Fitness-friendly vacation rentals in Key West

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, 201 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

5 out of 5 average rating, 14 reviews

Boat in Key West

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.

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, 36 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, 173 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, 24 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.

4.83 out of 5 average rating, 110 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.

4.91 out of 5 average rating, 179 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.

5 out of 5 average rating, 22 reviews

Apartment in Marathon

Waterfront Escape | Pool, Tiki, Breakfast & Marina

Stay at Mystic Mermaid, a brand-new luxury 1BR/1BA Waterfront Villa that sleeps up to 4 guests. Located on a scenic canal in the heart of the Florida Keys, this elegant retreat offers marina views and resort-style amenities including a pool, Tiki Bar, restaurant, pickleball & sand volleyball courts, fitness center, and complimentary breakfast. Perfectly located between Islamorada and Key West for the ultimate island getaway.

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, 200 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.

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, 147 reviews

Paradise found

Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.

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 Key West fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

5 out of 5 average rating, 8 reviews

Apartment in Islamorada

Ocean View Duplex Penthouse | Pool | Vista Two

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

5 out of 5 average rating, 5 reviews

An inviting pool area is surrounded by palm trees and lounge chairs, creating a relaxed atmosphere. The spacious pool is illuminated by soft lights as twilight approaches, with a tiki bar nearby offering seating and scenic views of the tranquil waters.

Apartment in Marathon

Marathon Studio on Lovely Gulf Front 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

The resort's outdoor pool area features a clear blue pool surrounded by lounge chairs. Palm trees are seen in the background, alongside a two-story building. Red umbrellas provide shade for guests enjoying the poolside atmosphere under a bright blue sky.

Apartment in Marathon

4.63 out of 5 average rating, 1,415 reviews

Standard 1 Bedroom King Suite with Balcony

Fitness-friendly condo rentals

A bright, sunny pool area is surrounded by lush palm trees and vibrant yellow buildings. The heated pool features a clear blue surface and is framed by wooden decking, inviting relaxation. A staircase leads to the second floor, contributing to the open and airy feel of the space.

4.84 out of 5 average rating, 50 reviews

Chagall’s Corner | Newly Remodeled!

5 out of 5 average rating, 36 reviews

The view from the screened-in lanai displays a serene boat basin framed by palm trees. A ceiling fan adds a functional touch above a round dining table, while boats are moored in the distance under clear blue skies.

Condo in Islamorada

Luxury condo with boat slip overlooking the bay

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, 66 reviews

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

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, 81 reviews

EYW Getaway

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

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

4.94 out of 5 average rating, 32 reviews

A spacious living area is featured, with comfortable seating arranged around a coffee table. Large sliding glass doors provide a view of the ocean and access to an outdoor seating area. Light-colored walls and soft furnishings create a bright atmosphere.

Condo in Islamorada

Just a Few Friends - Ocean View and Bring your Boa

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, 95 reviews

Key West Paradise

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

5 out of 5 average rating, 84 reviews

Home in Marathon

Luxury Boating Paradise+Pool+Sailing Kayaks

4.73 out of 5 average rating, 15 reviews

Island Villas Rentals

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

Flipper's Lagoons

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.