For the 50+ Traveler

1
Sweet Escape! Minutes to the Beach!

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Bedrooms: 1

Baths: 1

Starting Price: $82

This clean and simple rental duplex in Clearwater offers many options to travel the 2.2 miles to the beach, including free bikes and both a local trolley and ferry within walking distance. The home includes all the basic amenities for a comfortable stay, with bonus additions like a washer/dryer and covered parking. For those that travel with their pets, small dogs are welcome!

Mid-Range

2
NEW! Minutes to Beaches, Spring Training & MORE!

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Bedrooms: 2

Baths: 2

Starting Price: $90

This traditionally-decorated bungalow offers 7 sizeable rooms and a huge private fenced-in backyard. For the baseball fans, it's minutes from both the Philadelphia Phillies’ and Toronto Blue Jays’ Spring Training facilities. It's also a quick drive to Clearwater Beach, local golf courses, and excellent fishing areas. This rental specializes in long-term rentals for those looking to escape the cold weather at home and spend the winter in the brilliant Florida sunshine.

Splurge

3
Bay Breeze House Waterfront Home with Pool

Top Splurge
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Bedrooms: 4

Baths: 3

Starting Price: $233

This simply majestic waterfront home in Clearwater offers many deluxe amenities, including a 2,500-square-foot pool, hot tub, and adorable Floridian tiki hut! Each room is designed for maximum ocean views, wrapping guests in peaceful serenity. This beauty sleeps up to 10 guests, perfect for those looking for a vacation home large enough for the extended family.

Florida Keys

Bargain

4
Two-story Waterfront House With Dock

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Bedrooms: 4

Baths: 4

Starting Price: $196

This gorgeous, tastefully decorated waterfront property on Key Largo sleeps up to 9, making it ideal for a large family getaway. The dog-friendly house is equipped with all sorts of indoor and outdoor activities, including scuba and snorkeling gear, a hammock, a telescope, and even a popcorn machine for movie nights. It's steps away from the water and offers idyllic canal views from almost every room.

Mid-Range

5
Cozy, Dog-Friendly Home With Patio And Pool

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Bedrooms: 2

Baths: 2

Starting Price: $247

Attention snowbirds: This Key West retreat is only available for those looking for a long-term stay -- at least 28 days or longer. It's designed to provide all the comforts of home, including allowing the family dog to join. The robin's egg blue cottage has its own private pool and relaxing, fenced sandy backyard. It has extremely high walk and bike scores, meaning visiting most attractions and running errands are easily accomplished without a car.

Splurge

6
Modern Marathon Oceanfront Home

Best Of The Keys
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Bedrooms: 4

Baths: 2

Starting Price: $435

This oceanfront home on the canal in Marathon is complete with a private pool, boat slip, and a rooftop patio with a TV and fire pit. The house is stocked with tons of games and all-ages entertainment. It also comes with plenty of outdoor toys, including paddleboards, a kayak, and four bikes. Don't miss this five-star getaway!

Rosemary Beach

Bargain

7
Perfect Seacrest Beach Cottage With Pool And Bikes

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Bedrooms: 3

Baths: 2

Starting Price: $94

The "Beachy Keen" vacation cottage is located 200 yards from the magnificent white sandy beaches of Rosemary Beach. The huge community pool and veranda offer excellent relaxation options steps outside. Local restaurants and boutiques are within walking distance. This cute home is priced affordably for couple travelers but sleeps up to 7 people for larger family options.

Mid-Range

8
Amazing Location! Walk to Rosemary, Pool, & Beach

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Bedrooms: 4

Baths: 3

Starting Price: $124

This adorable home on Rosemary Beach has a second story front balcony and a five-star resort-style pool. Sleeping up to 11 people and starting at only $124 per night, it's a true bargain vacation home. It's conveniently located within walking distance of the beach and all of Rosemary Beach's favorite attractions, so you can explore without ever needing a car.

Splurge

9
Newly Remodeled Beach Home

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Bedrooms: 4

Baths: 4

Starting Price: $189

This home was remodeled prior to Summer 2020 and has all the newest and nicest amenities for a memorable stay. Don't miss the chandeliers and canopy bed! The private beach is a short half-mile walk, or use the owner-provided bikes. While it does not have its own private pool, access to the Seacrest neighborhood pool and jacuzzis is included. It offers plenty of outdoor lounging with a ground-level porch and second-story balcony.

Siesta Key

Bargain

10
1 Block from Siesta Key Beach With Private Heated Pool

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Bedrooms: 3

Baths: 2

Starting Price: $145

This beautiful modern home is only one block from the bustling streets of Siesta Key Beach and also includes a private screened-in lanai with a pool. In addition, there is plenty of outdoor seating. To complete the vacation, this home includes a garage, washer and dryer, barbecue pit, pool toys, beach chairs, outdoor shower, and free Wi-Fi.

Mid-Range

11
Ocean Beach Gleason Home With Heated Saltwater Pool And Spa

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Bedrooms: 3

Baths: 2

Starting Price: $274

This luxurious Ocean Beach Gleason home sits on a small lake offering gorgeous water views from the private saltwater pool and back patio dining area. The nearest public beach is only one mile away in Siesta Key Village, which is a quick walk or bike ride. The home includes all the beach toys required to easily kill a day in the sand.

Splurge

12
Coolest House in Siesta Key Village

Most Unique Home
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Bedrooms: 2

Baths: 2.5

Starting Price: $299

This super unique Siesta Key rental home has been dubbed The Coolest House in Siesta Key Village thanks to its Sarasota School of Architecture styling. The art enthusiast will absolutely fall in love with this decor. On top of the visual appeal, it's less than 10 minutes from the beach and includes a private pool and spa.

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