Fitness-friendly vacation rentals in Key Haven

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.

4.95 out of 5 average rating, 166 reviews

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

4.91 out of 5 average rating, 296 reviews

A shared pool area is depicted, featuring clear blue water and a thatched roof gazebo. Surrounding palm trees and lush greenery create a serene atmosphere. Lounge chairs are placed along the pool deck, complemented by the light-colored brick pathway paving the area.

Townhouse in Key West

Comfortable, clean, beautiful home Nov. Specials

Introducing a brand new property hosted by AirBnb Superhost Roy Svenningsen. This home was fully renovated in January 2019. It features all new furnishings, stainless steel appliances, new flooring, marble countertops, and top quality mattresses. I look forward to hosting you in this beautiful family oriented gated community situated across from the Key West Golf Course and only 3 miles from Duval St. The home comes with parking for 2 cars. I am always available to answer any questions. Roy

A large heated Olympic-sized pool is set within a tropical landscape, surrounded by palm trees and lounging chairs. The inviting blue water reflects the sky and is complemented by the nearby resort building, which features multiple levels and balconies.

4.92 out of 5 average rating, 194 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

1357 s f Luxury beachfront resort condo w/ all the amenities - beachfront heated Olympic pool, 3 lighted tennis courts, 20 man hot tub, tropical gardens, beach, saunas, Gym, BBQ Grills everything to make your vacation spectacular! You must be at least 25 years old to rent this property. This is a no animal rental due to extreme allergies of the owner. Thank you for understanding. Spalling work hs begun on the balconies of the other building this may impact your enjoyment of the pool

4.81 out of 5 average rating, 21 reviews

The Hunter 380 Sailboat is moored alongside palm trees, showcasing a sleek white hull and spacious deck. A tall mast with sails is prominently displayed against a clear blue sky, reflecting the tranquility of the marina setting.

Boat in Key West

Elegant Sailboat Stay

Nestle into comfort and embrace the charm of this Hunter 380 Sailboat , on waters edge at the Perry Hotel and Marina! This unique sailboat getaway offers a perfect blend of tranquility and adventure, providing an unforgettable escape for both relaxation and exploration enthusiasts. As a guest on Susquehanna you will be entitled to enjoy all the marina and hotel facilities including 2 pools , full gymnasium and regular free shuttle buses into the Old Town of Key West (15 minute ride)

A spacious swimming pool is surrounded by lush tropical greenery and lined with lounge chairs. Tiki-style huts provide shaded areas for relaxation, while the pool's clear blue water reflects the vibrant sky, creating a serene and inviting environment.

5 out of 5 average rating, 26 reviews

Funky Chicken Cottage with Shared Pool in Paradise

Funky Chicken Cottage is a charming and eclectic vacation rental located in Key West, just a short drive away from the main island on Stock Island, Florida. This 3 bedroom, 3 bathroom property is the perfect blend of comfort and style, with unique Martha DePoo art and Cuban art. The highlight of this property is the beautiful pool area, gated community. The property also features two parking spaces under the house, making it convenient for guests who are driving to the island.

A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.

4.89 out of 5 average rating, 147 reviews

Tropical Escape at Sunrise

We thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, basic cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests. Must be 25 and older.

4.9 out of 5 average rating, 62 reviews

The main saloon features wooden paneling, providing a warm atmosphere. Two leather couches flank a central table, while decorative pillows add comfort. A flat-screen TV is mounted above the seating area. A basket of towels sits on the table, with a soft rug running along the floor.

Houseboat in Key West

The simple life on Seaplicity!

Come stay on our beautiful & Super Comfy 38 ft Hunter Sailboat at the Perry Hotel & Marina! Start your morning with a fresh cup of coffee on board & "SIMPLIFY" your vacation with unrestricted access to all resort amenities! Two heated salt water pools, gym, laundry, and bathrooms and try one of the great restaurants onsite. Shuttle service takes you to old town Key West, leaving every hour from the hotel lobby.

4.95 out of 5 average rating, 44 reviews

A serene community pool is surrounded by lush tropical foliage and palm trees. Sun loungers are arranged along the edge, complemented by a shaded seating area nearby. The clear water reflects sunlight, creating a calming ambiance in the outdoor space.

Townhouse in Key West

Casa Coral

***Monthly Discount Promotion for August, September and October*** Bright and airy, Casa Coral offers an open living concept with all your vacation needs. This two bedroom, two and a half bath townhouse offers 3 outdoor balconies with seating and plenty of covered space to park your cars. Bikes and beach gear (no snorkel gear) provided. Please note: Bar-B-Q Grill pictured is now located in the carport below.

The expansive outdoor pool is framed by palm trees and surrounded by lounge chairs with blue umbrellas. The area is well-lit and features a shaded pavilion. The surrounding building showcases tropical landscaping, providing a relaxing atmosphere for guests.

4.9 out of 5 average rating, 153 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience. Great for Couples and Families We have a Website specific to our Condo where we offer special pricing, discounts and additional pictures Search-keywestbeachsidecondo

A light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.

5 out of 5 average rating, 41 reviews

EYW Getaway

Relax with the whole family at this peaceful place to stay. Our two-bedroom two-bathroom condo with complete kitchen is located at Sunrise Suites Resort. Amenities include shared heated pool, hot tub, tennis court and a basic gym. Our condo is located 1mile from the airport, 1.5 miles from the beach and 3.5 miles from downtown Duval St.

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.

4.78 out of 5 average rating, 300 reviews

Affordable Beachfront Luxury Condo Sleeps 6

My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!

A serene pool area is surrounded by lush tropical palm trees and vibrant landscaping. Sunlight reflects off the clear water, creating a calming ambiance. Nearby, a white lounge chair is positioned for relaxation, with a life preserver visible on the side.

4.89 out of 5 average rating, 114 reviews

Gone Coastal

Relax with the whole family at this peaceful place to stay. Completely renovated 3 bedroom 2.5 bath townhome in Coral hammock. Enjoy the pool and excellent location on Stock island. Walking distance to Roostica and Hogfish grill. Dogs are welcome but not over 25lbs. Pitsbulls are not allowed by hoa.

Popular amenities for Key Haven fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

A bright living area features light-colored furniture, including a comfortable sofa and armchair. A wooden coffee table is centrally placed. Art displays adorn the walls, enhancing the inviting ambiance. Nearby seating accommodates dining for four, with large windows allowing natural light to flow in.

4.91 out of 5 average rating, 82 reviews

Castaway Cove: Pet-friendly 2/2 condo near beach!

Private room in Key West

Hyatt Sunset Harbor Studio Oct 19-26th 2025

New place to stay

Key West Classic Gem

A spacious pool area features a large swimming pool surrounded by lounge chairs and vibrant blue umbrellas. Lush palm trees provide shade, and ocean views are visible in the background, enhancing the tranquil atmosphere of the outdoor space.

4.88 out of 5 average rating, 8 reviews

Henry's Penthouse On The Ocean

The exterior of a charming beachfront resort showcases three stories of pastel-colored buildings, framed by palm trees. A private marina with docks is visible in the foreground, while clear skies and vibrant greenery enhance the tropical setting.

Waterfront Sunset Harbor Club Resort+Amenites. 1BR

A vibrant pool area is surrounded by lounge chairs and palm trees, with azure water reflecting blue skies. The backdrop features the resort buildings and the ocean, showcasing an inviting atmosphere. Nearby, a terrace with tables can be seen for outdoor dining.

Beachside - Luxury for 8 people

A spacious living area is furnished with a comfortable sofa and armchair, complemented by a wooden coffee table. A large entertainment center features a television, while soft lighting enhances the room's ambiance. The space is adorned with tasteful decor and tiled flooring.

The Galleon Resort - Key West

A spacious living area features two sectional sofas arranged around a central wooden coffee table. A large flat-screen TV is mounted on the wall, and the open kitchen is visible in the background. Light-colored wood flooring and ceiling fan enhance the bright ambiance.

Cat Island Suite | Beautifully Renovated w/ Pool!

Fitness-friendly condo rentals

The image depicts a three-story building surrounded by palm trees, with a sandy beach in the foreground. A wooden dock extends into the water, providing access to the scenic waterfront. The clear blue sky enhances the serene atmosphere of the property.

4.75 out of 5 average rating, 405 reviews

HYATT BEACH HOUSE - Sleeps 4+2 - Great relaxation!

A large outdoor pool is framed by lounge chairs in vibrant blue, surrounded by tropical palm trees. The sun casts a warm glow over the water, while boats are visible in the distance, enhancing the serene atmosphere.

Condo in Stock Island

Private Parking & Waterfront - Grand Marina Suite

4.89 out of 5 average rating, 36 reviews

Key Lime Paradise 2BR w/ Pool, HotTub, Near Beach!

The living room is characterized by wood-beamed ceilings and spacious glass doors framing ocean views. Comfortable seating arrangements include a sofa adorned with colorful cushions. Natural light fills the space, enhancing the warm wood tones and elegant decor throughout.

4.93 out of 5 average rating, 28 reviews

Key West's Crown Jewel

An Olympic-sized swimming pool is surrounded by a sun deck, featuring lounge chairs and palm trees. The pool’s clear water reflects the sky, creating a serene atmosphere. The ocean and well-maintained tropical garden can be seen in the background.

4.79 out of 5 average rating, 24 reviews

Oceanfront Key West Condo

4.55 out of 5 average rating, 11 reviews

3-Bedroom 3-Bath Condo at Bayfront Suites & Marina

The bedroom features a spacious bed with light blue bedding against a red accent wall. A standing lamp provides soft lighting beside a dresser. A mirror reflects the bathroom area, showing a sink and light cabinetry with a contrasting black-and-white tiled floor.

4.7 out of 5 average rating, 210 reviews

Sunrise Suites Resort, Key West FL U #408 2bdr2bth

A serene pool area is surrounded by swaying palm trees, with inviting lounge chairs arranged for relaxation. The clear water reflects the sky, creating a tranquil atmosphere. A shaded seating area is visible nearby, adding to the vibrant landscape that leads towards the ocean.

5 out of 5 average rating, 6 reviews

Hyatt Windward Point Key West- Two Bedroom

Fitness-friendly house rentals

A well-maintained community pool is surrounded by lush tropical landscaping, featuring lounge chairs with blue umbrellas. The clear water reflects the bright blue sky and palm trees, creating a relaxing atmosphere for guests to enjoy.

4.87 out of 5 average rating, 69 reviews

Key West Paradise

A three-story townhome is presented, featuring a light blue exterior with multiple balconies. The structure is elevated on stilts with a staircase leading to the main entrance. A neatly landscaped area with shrubs surrounds the base, while a paved driveway is visible in the foreground.

4.92 out of 5 average rating, 85 reviews

Gone Coastal 2

A large resort-style pool is framed by tropical landscaping and palm trees, providing a serene atmosphere. The crystal-clear water reflects the blue sky, and a spacious deck is lined with lounge chairs for relaxation. A shaded cabana area is visible in the background.

4.92 out of 5 average rating, 13 reviews

Mermaid's Retreat at Coral Hammock Key West Islan

A well-maintained community pool is surrounded by lush tropical landscaping. Palm trees add to the serene atmosphere, while poolside loungers and a shaded area provide relaxation options. The water glistens under the clear blue sky, enhancing the inviting outdoor space.

4.85 out of 5 average rating, 161 reviews

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

The outdoor swimming pool features a circular design surrounded by tropical palm trees and lounge chairs. Bright blue umbrellas provide shade for guests, while the clear blue sky enhances the vibrant atmosphere of the gated community.

4.94 out of 5 average rating, 116 reviews

Paradise found

Island Villas Rentals

A well-maintained two-story house features light-colored siding and contrasting blue shutters. A spacious, welcoming front porch is framed by tropical plants and neatly arranged landscaping. Steps lead up to the front door, providing easy access to the entrance.

5 out of 5 average rating, 17 reviews

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

A serene pool area is surrounded by lush tropical landscaping. Several lounge chairs are positioned around the curved, clear blue water, reflecting the sky. In the background, two-story buildings line the pool, offering shaded areas under large umbrellas.