Fitness-friendly holiday rentals in Stock Island

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, 200 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

4.93 out of 5 average rating, 28 reviews

Boat in Key West

Waterfront Boat Stay + Resort Amenities

A Whim isn’t just a place to sleep—it’s permission to unplug and let vacation unfold naturally. Docked at the exclusive Perry Hotel & Marina, this 40-foot, 2-bedroom luxury yacht is tucked away from the crowds, while remaining just minutes from downtown Key West. Featuring inviting indoor and outdoor spaces for living, dining, and relaxing, it offers the perfect balance of comfort and adventure. Guests enjoy hotel amenities, including two pools, a gym, and three waterfront bars and restaurants.

Top guest favourite

Boat in Key West

5 out of 5 average rating, 12 reviews

3BR In Resort Village, Pools, Free Kayak & Shuttle

Experience the ultimate KEY WEST VIBE aboard our 3BR/2BA sailboat Located at the luxury Perry Hotel, you’ll enjoy ice-cold AC, palm trees, and salty air. Free Perks: Kayak, pools, parking, and free shuttle to Old Town! Full Resort Access: 2 sparkling pools & hammock park, 2 restaurants, ice cream shop, private bathhouse & Views of million-dollar yachts Live the island life w full access to all resort amenities. Your tropical escape awaits! This memorable place is anything but ordinary.

4.87 out of 5 average rating, 212 reviews

A crystal-clear saltwater pool reflects the sunlight, surrounded by lush tropical landscaping. Several lounge chairs are positioned along the pool deck, while vibrant palm trees and greenery create a serene atmosphere in the backdrop.

Townhouse in Key West

*Sparkling new kitchen* 3 bedroom/3 bath home.

Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 1 king size beds and two queen beds. The kitchen is fully equipped with modern appliances, dishes and cooking utensils. There is a new Whirlpool Duet washer/dryer installed. The salt water pool is perfect for lazing away your days. There is on street parking for two cars. The center of town is ten minutes away. An entire home for the price of one hotel room.

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, 34 reviews

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

Bring the whole family to this great place with lots of room for fun. Very clean, organized stand alone house with everything you will need to have a great stay! Fully stocked kitchen with a kuerig and drip coffee pot. Can have twin beds downstairs or convert into a king. Two king bedrooms upstairs. Each bedroom has its own bath! A queen sleeper couch in living room with a screen divider for privacy if needed. Steps away from the large heated community pool. Several nice restaurants around.

4.84 out of 5 average rating, 172 reviews

A shared pool area is surrounded by lush tropical landscaping, featuring palm trees and greenery. Sun loungers and umbrellas are arranged around the pool, offering ample space for relaxation. The water reflects the clear blue sky, creating a serene and inviting scene.

Townhouse in Key West

Charming Key West Vacation Rental 3bedrm/3bath

Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation. We have also updated the unit with new flooring throughout! Beach Gear is also available Beach towels, beach chairs, beach toys, floats and cooler. Baby / Toddler. Portable Crib, high chair & more. Items available upon request

4.83 out of 5 average rating, 23 reviews

Boat in Key West

43' Classic Yacht Views, Pools, Duval Shuttle

Create unforgettable Key West memories while staying on our long time charming liveaboard 43' Trawler. This 2 bedroom 1.5 Bath mini yacht will be the perfect home base for your adventures around town or to just sit and enjoy the incredible views and nature. Being at the award winning Perry Marina gives you all the amenities of a 5 star resort. 2 Pools, 3 Restaurants on site, free shuttle to town, hotel gym, laundry and all the charter and adventure options you could ever ask for.

4.82 out of 5 average rating, 108 reviews

A heated pool is surrounded by a spacious deck, featuring lounge chairs and a dining table with blue chairs. Beyond the pool, a pathway leads to lush greenery and the ocean view under a partly cloudy sky.

Home in Cudjoe Key

Palm Breezes! Room for Everyone on the Ocean.

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1.. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Grill, Jacuzzi. Full WiFi. TVs in every bedroom! Travel down our private dock way to the beautiful Cudjoe Bay, hop one of the many kayaks and take a healthy paddle with your friends/family or just enjoy the breathtaking ocean view while you sit on the porch.

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.

4.9 out of 5 average rating, 177 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.

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.

4.88 out of 5 average rating, 106 reviews

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

Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.

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, 199 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.

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, 314 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!

Popular amenities for fitness-friendly rentals in Stock Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

4.96 out of 5 average rating, 27 reviews

Casa Caribe 2bed2bath sleeps 6 beautiful decorated

New place to stay

Great Place for a week in Key West! Viel Spaß

A modern kitchen and dining area feature light tile flooring and dark cabinetry. A dining table, surrounded by upholstered chairs, sits adjacent to a comfortable living space with a sofa and decorative pillows. Natural light fills the room from large windows, inviting a pleasant ambiance.

5 out of 5 average rating, 12 reviews

Key West at Hyatt Beach House

A spacious resort pool is surrounded by palm trees, offering views of the beach in the distance. Lounge chairs are neatly arranged around the pool area, creating an inviting space for relaxation. Clear blue skies enhance the vibrant atmosphere.

4.5 out of 5 average rating, 66 reviews

Signature Double at Beachside Resort

A light-filled living area features a comfortable gray sofa and two accent chairs, arranged around a coffee table. A media console with a television is placed against the wall. Large sliding glass doors lead to a private screened-in porch, with views of palm trees.

4.91 out of 5 average rating, 11 reviews

Welcome to Your Tropical Key West Island Getaway

A fully equipped kitchen features modern wooden cabinetry and a stainless steel refrigerator. A countertop stretches along the space, complemented by a mosaic backsplash. Kitchenware is neatly arranged, and ample lighting illuminates the work area, enhancing functionality.

Beautiful Corner Condo Overlooking Pool

The image captures a scenic view of a zero-entry pool surrounded by lush palm trees and manicured landscaping. Several lounge chairs are positioned nearby. In the foreground, a straw hat and two beverages are placed on the poolside, creating a relaxed atmosphere.

Hyatt Resort Club at Beach House. 2 Bedroom/2 Bath

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.

4.92 out of 5 average rating, 12 reviews

Henry's Penthouse On The Ocean

Fitness-friendly apartment rentals

A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.

4.97 out of 5 average rating, 98 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

The image captures a waterfront view featuring a marina with several boats and yachts docked alongside wooden piers. In the background, a two-story structure with multiple balconies is visible, accompanied by palm trees and a historic red building, suggesting a blend of leisure and charm.

Beautiful Old Town Key West! Near Duval!

A crystal-clear pool is surrounded by vibrant blue umbrellas and comfortable lounge chairs. Lush palm trees frame the area, providing a tropical setting. The calm ocean sparkles in the background, reflecting sunlight against the sandy beach that leads to the water.

4.85 out of 5 average rating, 34 reviews

Key West's Crown Jewel

An open-concept living area offers a view of comfortable seating arrangements and natural light. The kitchen features a marble countertop and modern appliances. A balcony is visible through sliding glass doors, surrounding greenery enhancing the serene environment.

4.89 out of 5 average rating, 64 reviews

Key Lime Paradise 2bed 2bath Sleeps 6 Pool Hot tub

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.

4.83 out of 5 average rating, 30 reviews

Oceanfront Key West Condo

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.

4.99 out of 5 average rating, 80 reviews

EYW Getaway

4.59 out of 5 average rating, 106 reviews

Sunrise Suites Condo with Balcony - Shared Pool

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.

4.72 out of 5 average rating, 236 reviews

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

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.

4.88 out of 5 average rating, 93 reviews

Key West Paradise

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.

4.88 out of 5 average rating, 148 reviews

Gone Coastal

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.

4.87 out of 5 average rating, 23 reviews

Mermaid's Retreat at Coral Hammock Key West Islan

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, 144 reviews

Paradise found

4.79 out of 5 average rating, 14 reviews

Island Villas Rentals

Top guest favourite

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, 40 reviews

Funky Chicken Cottage with Shared Pool in Paradise

4.88 out of 5 average rating, 8 reviews

Seaside Retreat: Waterfront Home with private heat

A two-story house is presented with a covered porch on the main level, featuring bright red seating. The exterior is painted in soft yellow, with green shutters on the windows. Palm trees and landscaped greenery frame the property, enhancing the inviting atmosphere.