Pack your bags and spend the season in paradise! We picked the perfect monthly rentals on Florida’s Gulf Coast for snowbirds seeking sand between their toes. We only chose stays that are on or near the beach so you can sunbathe, swim, and collect shells. The warm waters of the Gulf of Mexico have almost medicinal effects, while Gulf Coast sunsets set the sky on fire.
Several of these monthly rentals feature resort-style amenities so you can play a round of tennis or golf and catch some rays by the pool. Many also feature lush, tropical landscaping. Not all of these options are pet-friendly, so be sure to read the fine print if you want to bring your pet along. Also, be mindful of the minimum stays. Enjoy 70-degree temps all winter long on the sleepy west coast of Florida in these fantastic monthly rentals!
Located on the southwestern tip of Florida’s Gulf Coast, Marco Island is one of the largest of Florida’s Ten Thousand Islands. It also happens to be the safest city in Florida. Be sure to explore the 32 acres of Tigertail Beach.
2 Bed, 2 Bath Luxury Beachfront Condo$1,386
This beachfront villa boasts panoramic views of mesmerizing sunsets over the Gulf of Mexico. The two-bedroom, two-bath unit includes an in-unit washer and dryer a private balcony.
It also comes with resort amenities, including premium access to the white sandy beach, two heated pools, a whirlpool, and a grotto pool, complete with a waterslide. Rent a poolside cabana if you really want to go all out! Stilts Bar and Grill has casual bites by the beach, while the Marketplace Express offers sustenance on the go.
Culture and sophistication along with white sands and pretty views make Naples a crowd-pleaser for solo travelers, couples, and families. Just a half-hour from Marco Island, Naples is part of Southwest Florida’s Paradise Coast. Explore Old Naples and check out the stunning Naples Botanical Garden.
2 Bed, 2 Bath On Golf Course$95
Stay in this two-bedroom, two-bath condo in popular Turtle Lake. It features a screened-in lanai, where you can enjoy your morning coffee or evening cocktail overlooking Quail Run Golf Course. Beautiful beaches are just minutes away, while Publix, Starbucks, and plenty of other shops and dining are within walking distance.
The master has a queen-size bed, while the guest has two twins. Resort-style amenities include a heated saltwater pool, a sauna, grills, lighted tennis courts, pickleball, shuffleboard, bocce ball, and a clubhouse with a library, gym, and pool tables. Keep your calendar full of activities with everything between water aerobics and coffee and donuts to bridge and bingo. No membership is required to play golf at Quail Run. Do keep in mind that there’s a minimum stay of 30 days.
2 Bed, 2 Bath Condo$525
Location, location, location! Stay in the exclusive and desirable multi-million dollar neighborhood of downtown Naples on tony 3rd Street South. Walk to the beach about a block and a half away and walk to the best shopping and bars and restaurants in town.
Upscale yet comfortable, this two-bedroom, two-bathroom is in a boutique building with only seven units. It comes fully equipped with a washer and dryer. There’s even private covered parking and an elevator or stairs to take up to the second level. Plus, there’s lush landscaping as well as lovely outdoor courtyards and fountains. There is a minimum 30-day stay, with a preference given to long-terms stays of 90 days or more.
Only 15 miles long and 5 miles wide, Sanibel Island is an oasis with a laid-back, cozy feel. About 25 miles south of Fort Myers, this quaint beach town is full of Old Florida charm. Not only does this snowbird destination sport one of the greatest shelling beaches in the United States, but it also has great fishing and birdwatching. Flying into the Southwest Florida International Airport makes this an easy journey from just about any major city.
2 Bed, 2 Bath Beachfront Condo
Offering much more than Gulf views, this two-bedroom condo on Sanibel Island is a weekly rental. Nestled on 23 acres, the resort offers beach access, where you can paddleboard, kayak, boat, fish, or have a bonfire as the sun goes down over the water. It’s also got tons of amenities — from the Gulf-side pool to tennis courts, complete with an onsite tennis pro. Treat yourself to an in-suite spa treatment.
Biking is a great way to get around the island. Pick up a bike from the concierge or, take a trolley ride. Relax in a lounge chair on the beach or a hammock under a palm tree with a book in one hand a daiquiri in the other. The Thistle Lodge and Coconuts Poolside Bar and Grill make sure you won’t go hungry.
Another small, family-friendly island, Captiva Island is Sanibel’s neighbor. Both islands are known for their undisturbed beaches, rich wildlife, and even richer cuisine. When you tire of shell-hunting, check out the island’s funky boutiques, coffee shops, and ocean-themed bars and restaurants.
4 Bed, 4 Bath House With Pool$850/nightly avg
Located in the Village of Captiva, Aah!!! Poppy’s Paradise is within walking distance of shops and restaurants. It is also just 400 feet from the beach and features private beach access. After a long day at the beach, relax in the private heated pool and connected hot tub. Other highlights include a ping pong table and pool table. This Captiva vacation rental can accommodate up to 10 guests and requires a minimum stay of seven nights.
1 Bed, 1 Bath Beachfront Condo$491/nightly avg
Not only does this stunning modern beachfront condo boast ocean views, but it also comes with a golf cart! Watch the sunset from your private balcony at this condo within the South Seas Island Resort. Guests can enjoy the condo pools that lie within steps of the unit, but do not have access to the main resort pool. An in-unit washer and dryer is handy for long-term stays. Although it is a one-bedroom, the condo can sleep up to five people thanks to the pullout sofa and Murphy bed. It comes equipped with beach amenities, too. Take the golf cart around the island to the Mucky Duck, Bubble Room, Doc Fords, Green Flash, and Starbucks.
Another prime spot for shelling, Manasota Key is a small beach community south of Sarasota and Venice. Relax on the beach of this 11-mile barrier island, or go paddleboarding or fishing.
3 Bed, 2 Bath Home With Pool$600
This Manasota Key home doesn’t just have its own pool, it also boasts easy access to the beach and bay. Access the beach across the street, while bay access and a shared neighborhood dock are also just steps away. Located on a peaceful shady private lane, it is still in close proximity to restaurants and shops on the south end.
Perfect for sharing with two families, this three-bedroom home can sleep up to 10. Both master suites have king-sized beds. The sitting room has a queen sleeper sofa, while the air-conditioned sleeping porch has a twin bed, a bunk bed, and a double bed that sleep four kids comfortably.
Minutes from Sarasota and Bradenton, Siesta Key is home to one of the best beaches in the U.S. according to our readers. From shelling to sunbathing, kayaking to day drinking, fine dining to boating, you’ll have no shortage of fun offerings in Siesta Key. Savor succulent crab or the fresh catch-of-the-day as you watch stellar sunsets. Collect shells along the waterfront as you watch seagulls and pelicans pick out their lunch. Read a book nestled on a comfy blanket on the sandy beach or enjoy a leisurely bike ride.
6 Bed, 4 Bath Home$1,254
Located in Siesta Key Village, just 60 steps from Siesta Keys’ world-famous beach, this Vrbo boasts a roof deck with beautiful ocean views, chaise lounges, and room for al fresco dining. This spacious, fully renovated two-unit property has gorgeous interiors. The rental includes the three-bedroom, two-bath penthouse as well as the three-bedroom two-bath unit below. Ask about additional accommodations for larger groups.
A block away, guests can find the best shopping, dining, and entertainment in the Village. Enjoy fresh oysters and other seafood, tropical drinks, ice cream, and gourmet donuts. Cars are not necessary on the island, but the rental does come with a parking spot.
Panoramic north, west, and south views of the Gulf make for amazing sunset views. Look for dolphins, sand dollars, and giant conch at nearby Sand Dollar Island. Your knowledgeable host can recommend the best fishing spots, restaurants, family-friendly activities, and more during your beach vacation.
South of Anna Maria Island, Longboat Key’s sugar-sand beaches are a playground for the wealthy. Although it’s a prestigious address, it comes with a laidback vibe. Flanked by beautiful sea oats, its beaches are perfect for swimming, boating, and kayaking.
2 Bed, 2 Bath Condo$241
Surrounded by recreation, views, and amenities, this spacious updated two-bedroom, two-bathroom condo is a beautiful upscale and private retreat. Lounge by the pool or at the beach, work out at the gym, play tennis or bocce, kayak, or fish. Shop and dine as you explore Florida’s west coast.
This rental comes with a washer and dryer and does not allow pets. There is a 30-day minimum stay. Longer-term rentals for the season are preferred. December through April and have a three-month minimum.
Old Man And The Sea Inn$319/nightly avg
Dubbed the Old Man and the Sea Inn, this Key West-style Victorian two-bedroom, one-bath apartment sits just eight steps from the sand path that leads to Siesta Key’s best beach. Get some sun on the balcony, lie in a hammock, dine al fresco, and walk to town for drinks or ice cream.
No car is necessary. Here, there’s no thru traffic, commercial businesses, or public parking. Walk to top beaches, outdoor activities, and dining, including the highest-rated seafood and Siesta’s only waterfront dining. Find fresh fish at Crescent Market or catch your own to grill up on the downstairs gas grill.
Home to some of the top snorkeling, fishing, and kayaking on the island, the limestone reef just 50 yards south features tide pools and colorful marine life. Search for miniature conch, dolphins, and turtles!
3 Bed, 3 Bath Waterfront Home With Pool$914
This three-bedroom, three-bath listing sleeps 10 and is actually made up of three large side-by-side one-bedroom units. Set on exclusive Heron Lagoon, surrounded by mangroves The Siesta Key Bungalows feature a heated pool, courtyard, and private on-water deck that’s great for lounging or eating outdoors.
Although this is a quiet escape from the resort super-highway, there’s no shortage of activities. One mile south you can find Turtle Beach, Palmer Bird, and Marine Preserve as well as a few good places to eat. A couple of miles north, there’s Crescent Beach where you can snorkle Point of Rocks reef. Several of the top restaurants and bars can be found in South Village. No stop signs or traffic lights make driving, biking, and walking a breeze. Plus, there are free taxi services and trolley rides day and night.
In addition to the swimming pool, onsite activities include kayaking, paddle boarding, and fishing off the dock. Relax in a hammock or lounge chair on some of the world’s best beaches. Indulge in oysters, gourmet donuts, daiquiris, ice cream, seafood towers teeming with shrimp and stone crab, craft beer, and enormous breakfasts. Listen to live music, rent a scooter or boat, and enjoy eco-tours through mangrove tunnels!
Anna Maria Island
Head past Sarasota to this gulf-side slice of serendipity. This quaint Florida beach town has resisted corporate development to preserve its idyllic feel of Old Florida. Anna Maria Island’s beaches have some of the whitest, softest, cleanest sand in the country. In fact, our readers voted Anna Maria Island public beach as one of the best beaches in the U.S. It’s also famous for its beachside horseback riding. Here, unique boutiques rub shoulders with local cafes and an impressive assortment of high-quality restaurants.
4 Bed, 4 Bath Beachfront Home$1,375
This luxury beachside home has its own heated pool and a balcony with gorgeous sunset views. With four bedrooms and four bathrooms, it sleeps eight adults. Tranquil yet close to everything, it is centrally located just south of downtown Holmes Beach. The property includes two parking spaces and offers easy access to the free trolley stop. Head south to charming Coquina Beach or north to Pine Avenue for restaurants and bars, boutiques, and Anna Maria City Pier.
This multi-level home features huge windows with views of the surf. Grill up some dinner on the balcony, or enjoy a fire on the back patio surrounded by Australian Pine trees, sea oats, and white powdery sand. A seven-night minimum stay is required.
4 Bed, 3 Bath Home$1,271
Located on the beach with sunrise views over Tampa Bay, Tropicottage is a charming, newly remodeled island getaway. Nestled in the quintessential Anna Maria Island North End neighborhood, this rental is just minutes from the heart of Anna Maria Village. Rent a golf cart and bikes to ride to restaurants, bars, and boutiques.
Dine alfresco in the lush, tropical courtyard, complete with a heated pool, lounge chairs, outdoor dining, and seating areas. A converted garage “man cave” with full bar, ping pong table, large flat-screen TVs, and comfy couch is adjacent to the pool.
This “mini-compound” is ideal for a family or group. In addition to the main house, there is a guest cottage. In the main house, the doors of the great room open out to the beach, as well as a putting green. Kids will love the cool coastal bunk beds with a door that opens to the pool courtyard. The second-floor master suite features a king-sized bed, an en-suite bathroom, desk, TV, a balcony overlooking the bay, and a large sun deck with sweeping views of the beach and courtyard pool.
In the guest cottage, you’ll find a private master suite, kitchenette with refrigerator and coffeemaker, a full bath, seating with a large flat-screen TV, and balcony with breathtaking water views!
St. Pete Beach
Set on a barrier island just west of St. Petersburg, St. Pete Beach is home to fabulous beaches, from Treasure Island to Tierra Verde. Check out Pass-a-Grille at the southern end of St. Pete Beach.
1 Bedroom, 1 Bath Condo$394
This beachfront condo overlooks the Gulf of Mexico and boasts an outdoor swimming pool. There’s only one bedroom and bathroom, but the couch pulls out to sleep four total. Your unit is assigned upon check-in, but is guaranteed to have a balcony.
Nearby activities include fishing, boating, windsurfing, waterskiing, scuba diving, tennis, golf, shopping, and dining. Nearby attractions include a playground, The Florida Aquarium, Florida International Museum, and The Dalí. Busch Gardens and Adventure Island theme parks can be found in Tampa, about 45 minutes away.
Close to the Tampa Bay region and all of its attractions, Clearwater is home to Clearwater Beach, which is widely regarded as one of Florida’s best beaches.
3 Bed, 3 Bath Townhome
Located on Clearwater Bay, this townhome has a game room and a boat slip! Housed in a newer townhome community, Brightwater Blue is within easy walking distance to Clearwater Beach, Beach Walk, restaurants, and shopping.
Guests have access to all three floors. The first floor has a two-car garage, the game room with pool table and ping pong top, as well as a lanai with views of Clearwater Bay. The living room, dining area, gourmet kitchen, laundry room, work station/computer nook, and large balcony with outdoor dining area are all located on the second floor. On the third floor, you’ll find the bedrooms. The master bedroom has a king-sized bed, a large balcony overlooking Clearwater Bay, a master bath with dual sinks, and a large walk-in shower. The second bedroom also has a king-sized bed, while the third has two full/double beds. For reservations of over six people, add $50 per person per night.
A deepwater boat slip can accommodate a 40-foot vessel, but keep in mind the water is only five feet deep at low tide. This rental comes with everything you need for a great day at the beach — including beach towels, a beach cart, and a cooler. Community features include a resort-style heated pool and spa, grills and outdoor entertaining area, and a beach rinse-off station.
Would you like your vacation home rental featured on TravelAwaits?
For even more vacation rentals on Florida’s Gulf Coast, check out: