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Florida's Pinellas Peninsula stretches from Clearwater Beach to St. Petersburg
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  • DestinationsUnited StatesFlorida

    20 Florida Monthly Rentals On The Pinellas Peninsula For Snowbirds

    Jeff Stahlhut
    Updated: March 07, 2023

    You’ve earned this. You’ve earned the time off. You’ve earned the chance to get away. And now it’s time for you and yours to take on full snowbird status and head to Florida for a month or more. Where do you start, you might ask? We’re here to help! If the Pinellas Peninsula in Florida sounds appealing to you (I’ve been, trust me… it’s appealing), then we hope you take a few moments to look at these 20 rental options selected just for you. These are nearly exclusively designed for couples — your chance to truly get away from it all!

    Videos by TravelAwaits

    While there are plenty more options than what we are offering up here, we think these rentals in Madeira Beach (Redington area), Sand Key/Clearwater Beach, Indian Shores, Treasure Island/Sunset Beach, and St. Petersburg/St. Pete Beach will be a great start to find what you’re looking for. If by chance you’re looking for more to do than relax on the beach or hang out in one of these amazing rentals, you’ll find lots to do in the St. Petersburg area and in Clearwater or Clearwater Beach. What are you waiting for?

    Clearwater Beach And Sand Key Snowbird Rentals

    Penthouse Suite At The Sandpearl Resort$602/nightly avg for long-term rentals

    This gorgeous penthouse suite, located within the Sandpearl Resort and Spa on Clearwater Beach, is situated on the top floor and was completely redone in May of 2020. The private balcony off of the living room affords you amazing views of the city and harbor. You’ll love the California king bed in the master suite that connects to the bathroom, large shower, and Jacuzzi tub. This suite faces to the east to give you a spectacular view of Mandalay Bay. This gorgeous gem is a must-see!

    Dreaming of Clearwater Beach – your dream vacation awaits you
    160 reviews
    Private vacation home
    5 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    loved every bit of my stay here but the cooler weather
    A great trip and a beautiful property! Has everything you need and more.
    Excellent stay at the Sandpearl, the best on the beach. The unit is gorgeous and met all of our needs.
    It’s our home away from home!!
    Beautiful, clean and updated suite!!
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    from USD 602
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    A Touch Of Paradise On Earth$261/nightly avg for long-term rentals

    This touch of paradise at Crescent Beach Club offers a 180-degree view of the Gulf of Mexico from the balcony and incredible views from every room. Located on the sixth floor, this luxury condo sits right on the beach, and the balcony — which includes a table, chairs, and loungers — is accessible from both the living room and master bedroom. Ready to head to the beach? This unit includes beach chairs, beach towels, and an umbrella. The Crescent Beach Club features two heated gulf-side pools, beach access, two outside spas, a tennis court, indoor hot tub, and much more. This condo and complex offer you the ultimate in luxury — don’t pass up on this one!

    Dreaming of Clearwater – your dream vacation awaits you
    43 reviews
    Condo
    2 Guests
    1 Bedroom
    2 Bathrooms
    Top guest reviews
    The condo was in a great location. There is a trolley service that makes traveling across the islands very easy and it is inexpensive.
    Super Clean, Awesome Views, Great Bed, Owner provides everything you need for Perfect Beach Day ie umbrellas, beach chairs, beach bag, small cooler. Beach is never crowded. This is our return stay it was so easy…even had a few Manatees swim by us in the water!!! Owner responds quickly….
    Beautiful view, extremely clean and great location.
    Easy process renting, great location, easy access, nice semi private beach ⛱️, Close to some great Restaurants, and close to Clearwater pier 60 if you’re looking to go there, would highly recommend!
    The condo was not only clean but had everything we could have needed. We enjoyed the pool, sunsets, the beach and even the pool table on the day it rained. Loved the location. Had a really great stay!
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    from USD 261
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    Remodeled Condo At The Crescent Beach Club$450/nightly avg for long-term rentals

    Enjoy a breathtaking view of the Gulf of Mexico from the 18th floor of the Crescent Beach Club 2 complex just steps from the beach. Newly remodeled and comfortably furnished, the floor-to-ceiling glass doors take you from your living room couch or king-sized bed to your balcony. From there, you are going to love the 180-degree westward view over a morning cup of coffee or an evening-time cocktail. Crescent Beach Club 2 is conveniently located and offers a pool, Jacuzzi spa, tennis courts, and more. You’re sure to love Pier 60 and all of the beautiful sights of Clearwater Beach!

    Dreaming of Clearwater Beach – your dream vacation awaits you
    42 reviews
    Condo
    2 Guests
    1 Bedroom
    2 Bathrooms
    Top guest reviews
    It was a very exciting experience. We had a very relaxing vacation.
    Our stay was in Mid May. The property is gorgeous, quiet and a fantastic location. (Not a place for a loud big group.) The beach is beautiful, not crowded at all
    The view from the deck and the beach is beautiful!! The condo has lots and lots of amenities. We enjoyed Clearwater tremendously!!!
    We had a great stay you couldn’t ask for a better view it was so beautiful. Wish we had better weather. I would definitely stay again it was so close to everything
    This was a beautiful clean condo that we will definitely plan to stay at again. The condo is very clean and has so much to offer. There was nothing more we could have asked for! Perfect location, beautiful sunsets, and great communication
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    from USD 450
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    Gorgeous Crescent Beach Club Hideaway$373/nightly avg for long-term rentals

    This gorgeous 12th floor hideaway at the Crescent Beach Club sits right on the beach and offers a 180-degree view of the Gulf of Mexico. Located on Sand Key, relax while watching the sailboats and dolphins from your kitchen or take in beautiful Florida sunsets from your patio — which comes equipped with a bistro table and chairs. Among the amenities at Crescent Beach Club are a swimming pool, fitness center, sauna, two hot tubs, and more. You’re going to love the views!

    Dreaming of Clearwater Beach – your dream vacation awaits you
    39 reviews
    Condo
    4 Guests
    1 Bedroom
    2 Bathrooms
    Top guest reviews
    The cleanliness was immaculate, as well as the modern furnishings… The kitchen appliances made me come home wanting to update my own! The view of the beach & ocean are spectacular, open the blinds in the kitchen/office area and you have an amazing 360° view of stunning Waters. The condo was stocked with everything you need minus food. They have extra blankets, plenty of towels including beach towels, even floor or table fans which we were pleased to find because we forgot ours! Nothing that is the renters fault, but, we didn’t find very many people staying there to be friendly. Not that we were there to visit them, but we are The type to speak to anyone we pass, especially if you ride an elevator together… the residence at this condo did not come off as those type of people… This would not deter me from staying here again, just a little heads up. This vacation was for pure relaxation and met that 100%! We took a vantage of the outdoor hot tub, the indoor Jacuzzi tub, the sauna, the pool, and of course the beautiful beach & ocean! You will have to drive or walk about 1 1/2 to 3 miles to get to any restaurants or markets, entertainment, etc. but the ones that we went to was delicious and we did enjoy a 3+ mile walk on a beautiful breezy day! If I had any critique whatsoever, it would be that the parking spaces are very tight and at times can be difficult to maneuver when the parking garage is full… Thank goodness my husband is excellent in this area! :)We look forward to staying here again in the future!
    Nothing really to do with the room, but the key to get everywhere was extremely annoying because you have to fidget with it for a minute to get it to work. The beach was honestly pretty gross. Sand isn’t soft what so ever and there’s shells all over. The room itself was pretty nice, the hot water wasn’t great for some reason but the place was nice to stay in.
    Would love to ret in the future. Great Condo. 🙂
    This condo is beautiful clean…… beach/oceanfront balcony to enjoy sunsets zero complaints perfect vacation definitely will stay here again !!thanks again to the owners for sharing their piece of paradise with us loved every minute!
    Beautiful beach views! Everything in walking distance!
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    from USD 373
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    Madeira Beach And Redington Area Snowbirds Rentals

    Ocean Sands Gulf Condo$196/nightly avg for long-term rentals

    Are you ready to book a trip to paradise? If so, this relaxing condo at Ocean Sands is for you! This 1,000-square-foot condo sits on the fourth floor, offering panoramic views and sunsets from the private balcony overlooking the Gulf of Mexico. The complex provides guests with a heated private pool and spa, accessible by keypad gates for residents and guests only. You’re going to love the living room and master bedroom, each of which feature a wall of glass that slides open to your balcony. Beach chairs, beach towels, and a beach umbrella are in the unit and yours to use, so you can pack just a little more lightly.

    Dreaming of Madeira Beach – your dream vacation awaits you
    82 reviews
    Condo
    4 Guests
    1 Bedroom
    2 Bathrooms
    Top guest reviews
    The views are like a poatcard. We had our morning coffee on the balcony listening to the waves and sat steps away on the beach itself to watch the sun set every night. Some nights dolphins were visible from the beach.The condo itself was clean and spacious and had everything we needed to enjoy our stay. Bruce was easy to communicate with and provided enough information so that we knew exactly what to expect, where to find what we needed, and how to access all parts of the fabulous property. 10/10 We would vacation here again!
    Absolutely loved the condo. Upon arrival the first thing we noticed was how clean the entire place was. It has everything you need to feel just like home. The living room area was very comfortable along with the beds in the bedroom. Loved having the double sink! Big bonus for us was the 5G wifi and the fact we could still connect while on the beach as we didn’t have data on our phones with not being from the States. The beach is beautiful and steps away along with the pool that was relaxing and refreshing after a day in the sand and ocean. Finally, the view is breathtaking from every single spot in the condo. We had morning coffee and dinner on the balcony watching the dolphins in the ocean and beautiful sunsets. The view is unbelievable!!!Bruce was so thoughtful and quick to respond to any inquires during our booking process. He even sent us a message on the day we arrived to check in to make sure we arrived safely and the condo was perfect. We loved our stay and will definitely be back. We didn’t want to leave.
    We just spent almost two weeks at Ocean Sands and we loved it! This property is in a great location, close to John’s Pass, lots of restaurants, grocery stores and shops and, most importantly…right on the beach! We watched dolphins daily from the balcony and beautiful sunsets every night. Bruce is terrific to deal with. He provided all information needed and answered any questions or concerns we had very quickly. The unit and the building are very well maintained and equipped. There are even some necessities there to get you started, or if you have forgotten things from home. There are beach towels, chairs and umbrellas available as well. The beds are very comfortable with nice quality cotton sheets (no microfibre). We look forward to spending time here again in the future…highly recommend this rental and owner!
    Wonderful Condo with everything you need!! Close to many restaurants & shops!! Would highly recommend!!
    This property was very clean and very well equipped with anything I needed! The view is priceless, the owner was easy to work with, and he provided detailed instructions for everything! Awesome stay!!
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    from USD 196
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    Secluded Condo Near John’s Pass$349/nightly avg for long-term rentals

    If amazing Gulf views in an upscale and secluded condo sounds good to you, then this rental is a must-see! Close to John’s Pass, restaurants, and shops, and within walking distance to Candy Kitchen, this centrally-located beauty is decorated “beach chic” with beach appointments throughout the living and family rooms. Step outside and enjoy your private, oversized balcony and watch the dolphins frolic!

    Dreaming of Madeira Beach – your dream vacation awaits you
    91 reviews
    Condo
    4 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    We have stayed in many different units all over St Petersburg/Treasure Island/Madeira Beach area. I loved everything that was provided. We have gotten to condos and there wasn’t even toilet paper, so we had to immediately go to the store. This condo had it all! Also, beach chairs, umbrellas, coolers, and even a box fan was provided. When flying down you can’t travel with all that stuff. We’ve had to go buy fans (for sleeping) then leave them. The only thing I would recommend is maybe getting some better pillows. Definitely worth the money and the location is perfect! We also like that there isn’t a bunch of units so it was quiter than some places we’ve stayed.
    The condo is a home away from home.It has all you need. You can walk to John’s Pass and find plenty to do and not have to pay for parking. We went to Salt Rock Grill for my birthday and it was exceptional. I can’t say enough about this rental.
    This condo is in a perfect location. It’s an extremely easy walk to the boardwalk and right on the beach with a great beach view. Updated appliances, clean, cozy, and big beach vibes. The pool and hot tub were great to hop in when you didn’t feel like making a day of it on the beach. The owner was extremely nice to work with. We had an awesome time!
    We visit Madeira Beach every year and really enjoy the area. This unit is clean, well supplied and we appreciated the washer/dryer in the unit. This was our second time to rent this unit and we hope to make it a third soon.
    Very nice property on a great beach! Awesome neighbors and nice amenities!
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    from USD 349
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    Updated Condo At Sunglow Seaside$204/nightly avg for long-term rentals

    This updated, ground-floor condo at Sunglow Seaside includes free lounger chairs, Wi-Fi, a barbecue, and a private umbrella patio table. This one is a great value! You’re going to love the majestic sunset views, your private covered porch, and your location — right in the middle of the three barrier reef islands. It’s located due north of Redington, Indian Shores, and Clearwater Beach, and is south of Treasure Island, Sunset Beach, and St. Pete Beach.

    Dreaming of Madeira Beach – your dream vacation awaits you
    35 reviews
    Condo
    4 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    Everything matched the description of property upon arrival. Communication was great with Doc and he kept us updated with weather alerts also! He checked in with us on numerous occasions make sure everything was good or if we needed anything further! Highly suggest this property and hope to return with family next time. This was for our honeymoon
    Man ! We loved our stay at the Sunglow, Dock is the man , He told me in the beginning I would love it , He was so right , Everything was spot on, Were looking forward to coming back , Thank a Bunch
    Laid back living. Sunsets and beach very nice.
    Property was very convenient to the beautiful beach and within walking distance to many restaurants and other shopping. Had some difficulty connecting with the manager to get check-in information, which wasn’t automatically provided with the rental agreement/notification.
    Sunglow Seaside is amazing & I wouldn’t think of going anywhere else to stay. Doc is the owner and he’s very nice. It’s just steps to the beach and people are so friendly here. I love it. The condo is beautiful – I love Doc’s decorating! For me this condo is an awesome vibe. There’s so much to do around here that’s walking distance. I could go on and on. I’m in my happy place for sure, I could stay forever! Really wish I could. The service is very good (I had to call doc at 1 am he’s so nice) #SaveTheTurtles
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    from USD 204
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    Tropical Beach Cottage At Madeira Beach$250/nightly avg for long-term rentals

    This “Old Florida” tropical beach cottage is full of modern amenities, privacy, and charm. You’ll have everything you need here including a fully-equipped kitchen, beach towels, and chairs. This location offers you no streets to cross to get to the beach, and is within walking distance to John’s Pass, restaurants, shopping, dolphin watching, and more. This little cottage is bright and fun and waiting for you!

    Dreaming of MADEIRA BEACH – your dream vacation awaits you
    119 reviews
    Cottage
    6 Guests
    2 Bedrooms
    1 Bathroom
    Top guest reviews
    Wonderful property that met our vacation needs! Everything you needed at your fingertips! Reviews re: street noise are true- so if you are looking for a quiet place and noise affects your sleep this may not be the place. Reviews re: bathtub not draining during showers were also true.The place was clean and beautifully decorated. Restaurants, beach etc so close!!! The host is wonderful and quick to respond. We would recommend this place!!
    2nd year we have stayed in this location…fantastic as always! Property is very clean and very well kept! Location is perfect! Walking distance to just about everything! Thank you
    This was the perfect little cottage for a sister’s get together! Great location with all the amenities thoughtfully available. Everything was exactly as described and pictured on the site. Our host was amazing and very responsive with any and all questions. Steps to the beach and shops. We would definitely come back for our next get together!
    The property was super cute, plenty of room for hanging out. The location was perfect, soo close to the beach and John’s Pass. An extra bonus was the availability of beach chairs available for use. Wonderful, would 100% be back.
    Will not stay there again. Had to pay for place to be cleaned but had to wash dishes before we could use them.
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    from USD 250
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    Indian Shores Snowbird Rentals

    One-Story Indian Shores Beach House$226/nightly avg for long-term rentals

    There are a lot of options to choose from when looking at beach rentals, but when you come across the chance to stay in a beach house, you can’t pass it up! This cozy one-bedroom house is one of the last beach houses on Indian Shores, and features granite countertops, a microwave, stove, toaster, coffee maker, refrigerator, Wi-Fi, and is near lots of local amenities. Jet ski rentals and fishing charters are close by at John’s Pass. Or head the other direction 10 minutes and check out Clearwater Beach. You don’t want to miss out on this one!

    Dreaming of Indian Rocks Beach – your dream vacation awaits you
    155 reviews
    Cottage
    4 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    Stay was wonderful. Small but has everything we needed for short stay. Beach accessible right out back door.
    Place is in a block where it doesn’t look attractive. Very small bath room. We had an issue with a/c rambled like it was so noisy that it was difficult to sleep. Just make sure they have fixed this problem. Other wise would recommend it.
    location on the beach cant be beat, small cottage, best for 2, not much else to do but very relaxing!
    This was by far my favorite VRBO experience. The place was perfect and just what we needed. It had everything you would need and it’s location on the beach was fantastic. We will definitely be back!
    We were looking for a place to be nestled cozily by the beach, and this cottage was perfect for our family of 4. The kids enjoyed the water so much and they had a cute beach shed with tubes and other fun stuff for them. The beach is not crowded which is a bonus. Wifii connection was decent and there was cable. If I wished for one thing, it would be laundry, but we really can’t complain…this place is great!
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    from USD 226
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    Indian Shores Cottage With Old Florida Charm$347/nightly avg for long-term rentals

    From your porch to the sand, the beachfront cottage with old Florida charm is just steps from the Gulf of Mexico and offers fantastic sunset views! With a private carport, you can park your car and enter this house without climbing any stairs. Inside, you’ll find an open-floor plan, well-stocked kitchen, new bathroom, and new furnishings. Add the fun beach decor inside and this cottage is definitely worth checking out.

    Dreaming of Indian Shores – your dream vacation awaits you
    95 reviews
    Cottage
    4 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    We had a fabulous time here. The view was perfect, the space was great and I don’t think there was anything that could make it better. We just loved looking at the water. We live on an island but we are 2 blocks in so we don’t have that kind of view. The restaurants we went to were also very good. Guppy’s was our favorite but Crabby Bill’s was good, too. We didn’t do as well with JD’s so we only went once. All in all it was a great 4 nights. The bed is also very comfortable.
    This was our second time staying, and we loved it just as much as the last time. The location can’t be beat. We’ll definitely be back!
    We enjoyed our stay in Indian Shores! Beautiful hidden gym right on the beach with the busy hustle of Clearwater just 15-20mins down the road.
    Exactly as advertised. Literally steps from the beach! Small, but includes absolutely everything you need! Perfect for a couple or family of 3 like ours. The kitchen and bathroom are updated and function well. Neighborhood is great. There is a mini mart very close by for food, drinks, or any other items you might need. We also loved the pizza place which was just a short walk to get to.
    Clean, quiet get away! Great communication with owners. Tons to do in the area. Would highly recommend this beautiful place.
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    from USD 347
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    Indian Shores Resort Villa$172/nightly avg for long-term rentals

    Just steps from Indian Shores Beach, this third-floor condo comes in a little less expensive with the caveat that it does not have a balcony or an ocean view. It does, though, sit just steps from the beach and is conveniently located at Villas 3 Resort. Here, you’ll find easy access to plenty of leisure and recreational activities. Be sure to take advantage of the heated pool and patio that overlook the Gulf of Mexico!

    Dreaming of Indian Shores – your dream vacation awaits you
    40 reviews
    Condo
    4 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    The location was absolutely perfect, we couldn’t have asked for a better place to stay. The home had everything we needed & it was such a great location that we really had no reason to even leave the property. The pool was clean, guests were respectful, and the patio with grills was a great hangout for us. We will definitely be back!
    This condo is located in an interior airshaft, four walls surrounded by four walls. There is no exterior view other than looking at the front doors of other condos that face the outside. The garbage shoot for all condos is located on the back wall of this condo, which is the bedroom, so you hear everytime throws their trash in all 77 condos. All 77 condos have access to the ONE elevator. Their is only one Handicap parking space for entire complex. This condo was recently renovated very tastefully BUT no matter how much lipstick you put on a PIG it is still a PIG
    Robert and Tetyana have been the best VRBO hosts and were most accommodating when I had to reschedule my trip, twice, due to a family illness. Third time was a charm and their sweet little place was so clean, welcoming and had everything I needed for my stay. The bed and pillows were so comfortable and the beach chairs, umbrellas, towels and cooler were all put to good use. The location was absolutely perfect with a beautiful, white sandy beach as you exit the condo. The only thing I did miss was a view out the windows (they open to condo’s interior courtyard), but in the end it didn’t matter as I didn’t spend much time inside anyway. I loved my stay so much, I even extended it a couple extra days. Thank you both for a wonderful trip and you will definitely hear from me again!
    Very comfortable, beautiful site seeing , pool and beach , close to restaurants. Great communication with the property manager
    The apartment was cute, comfortable, clean, & had everything we needed for the weekend. They even had beach towels, chairs & umbrellas, so no need to bring. No beach view from room didn’t bother us at all as we already knew it from the description. Robert was easy to contact & replies right away. Parking is across the street but was not an inconvenience until it was pouring down rain. We had left our umbrella in the room, so that’s our fault! Maybe wouldn’t recommend to someone who is elderly to cross the street, but it really was not a big deal to me & my teenage daughter. We immensely enjoyed our short stay & would stay again! Can’t beat the price for a short getaway on beachfront property.
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    from USD 172
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    A Little Slice Of Heaven In Indian Shores$280/nightly avg for long-term rentals

    With nothing obstructing your private, breathtaking ocean view, this first floor beachfront condo is a little slice of heaven on Indian Shores, offering quick and easy access to the sand and shore. Located directly across from the highly-rated Salt Rock Grille, Indian Shores sits conveniently close to Clearwater, St. Petersburg, and Tampa. The breathtaking ocean view offers the ultimate in relaxation!

    Dreaming of Indian Shores – your dream vacation awaits you
    50 reviews
    Condo
    4 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    This property was amazing and the view was just beautiful ! My husband and I will be back.
    Very nice. Loved every minute of it. Very clean, very accessible. Thank you from the both of us. We will definitely be back.
    This property was fantastic. Perfectly located on the beach and across from a great coffee shop. The incredible Salt Rock Grill restaurant was also within a very short walking distance (practically across the street). The owers were wonderful to deal with and the condo had everything anyone could need for a beach vacation. It also had all you need to relax inside and feel right at home – big screen TV and comfy sofas, flat screen TV in bedroom, fully equipped kitchen. It was extremely clean and comfortable. My husband and I hated to leave and will definitely book here again!
    Having stayed in this condo last year, we loved it so much we decided to return. Extremely clean, comfortable and incomparable views of the sunset. We didn’t use them but there are beach chairs, an umbrella and a few beach toys provided. We will definately consider staying here a third time in 2023.
    We couldn’t have asked for a better week at the beach. The condo is as advertised. Great furnishings in every room. A wonderful living space that looks right out to the ocean. We were literally steps from the beach. The kitchen had everything one would need. The bedroom is large with a closet full of stuff to take to the beach. Good communication with owner. Indian Shores is great- the beach, the restaurants and the people. Can’t say enough good things. We hope to return in the fall!
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    from USD 280
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    Treasure Island And Sunset Beach Snowbird Rentals

    Beachfront Parrot-Dise In Sunset Beach$276/nightly avg for long-term rentals

    If you’re looking for a beachfront “Parrotdise” condo with beautiful beachfront views of the gulf, then this vacationer’s delight might just be for you! Equipped with a large, private deck, you’re going to love watching the sea birds, parrots, and dolphins. Or take long walks on the beautiful, sandy beach. Looking to relax after your walk? Have a seat on the garden patio that overlooks the beach and take in a gorgeous Florida sunset. There are lots of amenities nearby — enjoy “Parrotdise” on your next vacation!

    Dreaming of Treasure Island – your dream vacation awaits you
    67 reviews
    Apartment
    4 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    Everything was awesome. Location was wonderful. The view was worth the price by itself.
    Great property! Really close to the beach and Caddy’s is just a 5 min walk away. Publix is about a mile so about a 30 min walk if you do not have a car. We arrived in the dark and the unit entrance is off to the side up some stairs, we missed that and had to call JoAnn. Property is really well appointed and we loved it. We extended our stay and JoAnn was accommodating and was able to get us into another unit of hers on the same property. Our only issue was the Internet at both locations was sketchy the entire trip. I had to use my hot spot most of the time, but that was my only issue. Aside from that, I would recommend!
    We thoroughly enjoyed our stay. It was great waking up with a cup of coffee just listening to the waves hit the beach from the deck. This beautiful & peaceful property is just steps from the water. We hope to be back again!
    Wonderful experience at this beautiful location. Excellent host.
    Condo was as advertised, right on the beach. Property was clean and very comfortable. Easy check in and check out. The Sunsets were spectacular, very fitting for the beach to be called sunset beach. This was our third visit and can’t wait for number four
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    from USD 276
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    Island Breeze At Bilmar Beach Resort$180/nightly avg for long-term rentals

    Located in the heart of Treasure Island, this Island Breeze motif condo is the perfect spot to take in stunning views of the Gulf of Mexico from your private balcony. Step out of your cozy unit at the Bilmar Beach Resort to take a dip in one of the heated pools, located directly beneath your unit. Or sit on your balcony to sip morning coffee and listen to the relaxing ocean sounds. This gem offers beautiful views with lots to do nearby!

    Dreaming of Treasure Island – your dream vacation awaits you
    103 reviews
    Condo
    2 Guests
    1 Bathroom
    Top guest reviews
    All you need right here. Comfortable room, clean pool, (2).Restaurants and entertainment. Park your car, really no need to go else where. Just what I was looking for. Already looking to book again. Thankfully.
    The shower was dirty the shower curtain was very dirty. The hot water to up to 25 minutes to get hot. Then it still was just warmThe floors had a fair amount of sand on themLocation was GREAT
    This was our fourth trip to stay in 242 I really enjoyed the fine upgrades the bed was extremely comfortable the room was clean as always Coral was very gracious host and very easy to communicate with everything Within walking distance and half of what you would pay to stay at the hotel
    This place exceeded our expectations! The room provided many little things, such as silverware, cups, and some bath products, which was nice in case we forgot anything. The room is actually a lot more spacious in person too. The location was unbelievably incredible, with a bar/restaurant and the beach just steps away (not to mention a pretty cool view from the balcony). The resort is in walking distance to everything and anything you need! We will definitely be coming back!!!
    This was our 1st time at Treasure Island . We had a wonderful time the room was nice clean bed was comfortable. Everything was right there you didn’t have to even drive anywhere. The only downfall is the walk up the the tiled area going down the ramp I slipped and fell L so beware when you’re 1st coming up the walkway why
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    from USD 180
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    Beachfront Condo In Sunset Beach$283/nightly avg for long-term rentals

    With gorgeous beach and gulf views, this beachfront condo with a private deck offers the sights and sounds of gentle waves, sea birds, parrots, dolphins, and more — all at a convenient and centrally-located spot. You’re going to love the cozy interior of this 600-square-foot unit. But, you’ll no doubt love even more relaxing under the shade tree while taking in gorgeous sunsets on the garden patio that overlooks the beach. Check out the provided photos for those amazing deck views!

    Dreaming of Treasure Island – your dream vacation awaits you
    73 reviews
    Condo
    4 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    This is one of the best places that I’ve stayed at! The deck right off the sand, and beautiful Gulf of Mexico, makes it well worth the price. Jo Ann was a great host, and a great communicator. The bed was super comfotable and everything in the condo was in perfect condition. A perfect place to enjoy the beach and all that Treasure Island has to offer!
    We stayed the weekend before hurricane Ian. Our gracious host was concerned for our safety and we left early and she refunded our remaining monies promptly. It is a perfect getaway and we truly love it there! This was our 3rd trip here and we plan to return in the future ❣️
    We had a fantastic week at Jo Ann’s condo! Perfect family spot, spent most of the time on the beach and relaxing on the deck. The sea turtle nests were so great to see! Perfect little condo with everything we needed to make breakfast and lunch! Too many wonderful beach restaurants to eat dinner in! Just a 5 min beach walk to Caddy’s, a fantastic beach bar and grill. Nothing like toes in the sand and an ice cold beer in your hand! We would absolutely stay here again!!
    This place was amazing for the price and location! Perfect access to the beach and all the amenities Treasure Island has to offer. The rental itself and the property owner were such a delight. My only complaint was the people below us playing extremely loud music at 3 in the morning and their very loud dog which came charging at my 3yr old one evening when we were hanging out outside and the owner no where to be seen. However, this is nothing negative against the property itself or the owner just the people staying below us which was out of anyone’s control really.
    This condo is absolutely perfect. It is in an excellent location and is extremely convenient to the beach. There are only a few condos in the building and we didn’t hear as much as a peep from any of the other guests. Loved being able to see the waves from the deck. The trees at the beach also provide awesome shade for most of the day. This was our first time to Treasure Island and We were blown away. When we return, we definitely will look to book this condo again. 5 stars!
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    from USD 283
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    Harbor House Sunset Beach Getaway$172/nightly avg for long-term rentals

    Just steps from the beach, the Harbor House Sunset Beach Getaway is a newly-renovated condo with amazing views of the Gulf of Mexico out front and the Intracoastal Waterway in the back. With a heated pool at your disposal, take advantage of your easy beach access — the beach towels, beach chairs, and umbrella are provided. Harbor House is walking distance to local restaurants, shops, and bars. This one is cozy and clean at a reasonable price!

    Dreaming of Treasure Island – your dream vacation awaits you
    15 reviews
    Condo
    2 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    Had a great getaway! Long time coming. Needed to get back to normal.
    Both the condo and the host were gems. The host, Jen, was quick to answer all questions and was genuinely interested in making sure we were comfortable during our stay. The condo felt like home. It was clean, had all the amenities, bed was extremely comfortable, and location was excellent. Steps away from the beach, views of the water both from balcony and bedroom. Restaurants and shops nearby. Beautiful sunsets. If I could give it more than five stars, I would.
    This was a great unit, which along with the perfect weather, made for a really enjoyable one week stay at Sunset Beach on Treasure Island. We have stayed in this area several times, but first time at this unit. The unit was clean, very well kept and convenient to the beach, local restaurants/bars and shopping in the area; most cases just a short drive or walk. The owners were very easy to work with and very accommodating in helping with any questions or needs. We would definitely stay here again with our next journey back to the area. Thank you, Jen and Traci, for helping to make our stay a GREAT one!
    Clean, pleasant, relaxing accomodations. Jen was available and very helpful. Highly recommend.
    Great experience with this rental thanks to the super owners who were beyond accommodating on so many levels. Condo had all the amenities you could ask for and in such great shape. Thank you for everything Jen and Traci!!
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    from USD 172
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    St. Petersburg And St. Pete Beach Snowbird Rentals

    Pass-A-Grille Studio In St. Pete Beach$129/nightly avg for long-term rentals

    This studio located in the heart of Historic Pass-A-Grille sits right on the Gulf of Mexico — a perfect spot for your cozy getaway! Completely remodeled and fully furnished, Pass-A-Grille is close enough to the action to be convenient yet remains a quaint beach community. This one is definitely worth a look — you’ll be glad you did.

    Dreaming of Saint Pete Beach – your dream vacation awaits you
    161 reviews
    Apartment
    3 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    Place is exactly as described. The location is supreme. Pass-a-Grille is the very end of St Pete Beach. A very cool bohemian vibe. The beach is narrow here but still not too crowded especially mid-week. The shared second-floor outdoor space in the building is PERFECT for viewing the sunset. Spectacular. The unit is completely utilitarian. Everything you need—beach chairs & towels, an umbrella, a couple of boogie boards, adequate kitchen utensils, etc. The room itself is dark. If you need to spend time indoors during the day, you might consider other options but that is nearly the only drawback. It’s not large but we happily sacrificed space for a great nightly rate. Unit was very clean. I’d come back again for sure.
    We love staying at this unit! It’s so close to the beach and has a great second floor shared balcony! We’ve stayed several times and the unit it always clean and comfortable! We’ve already booked for next year too!
    Our Small Piece of Paradise !!
    Cute little rental. It had everything we needed and the best part…. right across the street from the beach! There are also 3 restaurants and an ice cream parlor less than a block away. Don’t miss out on this one!
    Living in Florida is everyone’s dream.but for those who live here we treasure our staycations.this is my third time here,a true little gem.miss it already, until we meet again❤
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    from USD 129
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    Tropical Courtyard Paradise$125/nightly avg for long-term rentals

    This Tropical Courtyard Paradise offers a private entrance and courtyard along with a spacious heated pool. Just a 1-minute walk to Upham Beach or the fun on Gulf Boulevard, this unit comes at an affordable price in a premium beach location. Ready to hit the pool or the beach? A cooler, beach chairs, pool noodles, flip flops, a boogie board, beach towels, a carry-on wagon, and more are available for you. Be sure to take the time to relax on the private, shaded courtyard!

    Dreaming of St. Pete Beach – your dream vacation awaits you
    6 reviews
    Condo
    3 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    Very cozy, well appointed 1 bedroom. Ground floor, private entrance with patio., close to Upham Beach and restaurants. The owners were delightful to deal with and thought of all the details to visit gteat@
    We have stayed at this property twice now and would love to stay again. Perfect location, great outdoor space, property owners are great to work with.
    Loved the place..close to beach and many restaurants within walking distance!!
    Excellent location. Clean and the hosts were extremely helpful. I would stay again.
    Excellent location. Clean and the hosts were extremely helpful. I would stay again.
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    from USD 125
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    Gone Gulfin’ At Pass-A-Grille$259/nightly avg for long-term rentals

    Don’t come looking for us, we’ve Gone Gulfin’! This corner unit is nicely decorated and provides easy access to historic Pass-A-Grille. You’ll spend your mornings enjoying coffee and evenings sipping a cocktail on your porch, and in-between, spend some time in the heated pool. Pass-A-Grille is located within walking distance of shops, restaurants, and bars on 8th Avenue, or stroll a block to the Merry Pier for bird watching, bike rentals, fishing, or a sunset cruise. 

    Dreaming of St Pete Beach – your dream vacation awaits you
    96 reviews
    Condo
    4 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    Spent 8 days in this lovely condo. Quynh was only a phone call away if we had any concerns or questions. No concerns. Unit is directly across from the beach. Dewey’s restaurant was in the next block and our meal was excellent. We hope to return some day.
    We were steps away from the beach at this property. It was such a convenient place. The first time I stayed at a smaller condo but didn’t have any regrets – once seeing it showing up, I knew it was worth the money for the week. Reaching out for any needs, were met immediately & communication was always open. We stayed in the 1 bedroom, pull out couch unit with us 2 adults and our two daughters. Everything was supplied. Grocery store, fast food & restaurants were a short drive although there are ice creams and places to eat within steps from condo. Not a disappointment and would book again.
    Thank you again Quynh for a most enjoyable stay at Gone Gulfin. Everything was great and we appreciated your extra consideration. Look forward to my next visit
    Thoroughly enjoyed my week visit. Clean, comfortable place in an absolutely perfect location. Love the small community vibe and the sunset celebrations on the beach at Paradise Grille. Can’t wait to return!
    We’ve been vacationing in the St. Pete/Sarasota area for over 35 years. We’ve always loved Pass-a-Grille and this was our first week-long stay in PAG. Location was perfect and the home was not only clean and beautiful but also had everything we needed and more. We’re already talking about when we can get back. Thank you for being such perfect hosts!!
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    from USD 259
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    Sweet Spot In Downtown St. Pete$113/nightly avg for long-term rentals

    This Sweet Spot in Downtown St. Pete is within walking distance of just about everything! This spectacular condo is near some amazing museums, including The Dali, Museum of Fine Arts, Holocaust Museum, and St. Pete History Museum, to name a few. Is the restaurant scene more your thing? There is a long list of restaurants and breweries around. Or pay a visit to the local shops, art galleries, music venues, or boutiques. If you’re a sports fan, head over to Al Lang Stadium to watch the Tampa Bay Rowdies play soccer, or Tropicana Field to take in a Tampa Bay Rays baseball game. There’s so much to do — this one is a must-see!

    Dreaming of St. Petersburg – your dream vacation awaits you
    8 reviews
    Condo
    2 Guests
    1 Bedroom
    1 Bathroom
    Top guest reviews
    Wonderful location, accommodations and host
    Cant go wrong. Everything is easy to walk to. Publix is only two blocks away. Other tenants in the building seem to be friendly. The laundry room was never busy. When you come enjoy this great city.
    This place had absolutely everything I needed for a very comfortable stay. Everything in the place was very high quality, from the bed to the couches to even the bath towels. The owner was very quick to respond and checked in to make sure I had everything I needed for a nice stay. Also, the location was great and within walking distance to many places. This has been one of the best rental experiences I have had.
    This property is just far enough from downtown to be quiet yet close enough for easy walking/biking to attractions and sustenance. Grocery and drugstore are three blocks away. The owner was always helpful and changed out the shower head and even a light bulb during our stay. Saint Petersburg is full of great galleries and museums so you will never be bored. Take the Crossbay Ferry to Tampa for a fun ride and great views. From the dock you can ride the free trolley to Ybor City.
    I loved my stay at this comfortable, cozy and quiet apartment in the heart of downtown St. Pete. The host provided everything you could possibly need in terms of household supplies and necessities. She also was very considerate of my long and exhausting travels and accommodated my late arrival with a thoughtful presentation of comfort food and drink to get me through the next day. Off street private parking was also a plus. I highly recommend this rental.
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    from USD 113
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    To check out even more snowbird rentals around Florida:

    • 23 Monthly Rentals On Florida’s East Coast Perfect For Snowbirds
    • 19 Monthly Rentals On Florida’s Gulf Coast Perfect For Snowbirds

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