Fitness-friendly holiday 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, 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

ParksWalkabilityPool

4.93 out of 5 average rating, 27 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.

ConditionValueHospitality

5 out of 5 average rating, 12 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.

Check-inLocationGetting 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

BikingGetting aroundLocation

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.

BikingViewParking

4.82 out of 5 average rating, 108 reviews

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.

BikingQuietWi-Fi

A modern kitchen is showcased, featuring stainless steel appliances, including a microwave, oven, and refrigerator. Sleek white cabinetry complements the light-colored countertops. A view into the adjoining space is visible, hinting at a well-lit dining area.

4.9 out of 5 average rating, 176 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.

BikingBathroomView

A light-filled living area is furnished with a large sectional sofa and a wooden coffee table. A ceiling fan features tropical leaf blades, while a wall-mounted television is visible. The space opens to a breakfast bar with seating for four, leading into a bright kitchen.

4.88 out of 5 average rating, 105 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.

DecorAccessLocation

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.

BikingCheck-inHeating

4.99 out of 5 average rating, 80 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.

BikingDecorFamily

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!

BikingWalkabilityLayout

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.

4.91 out of 5 average rating, 165 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

BikingSleep qualityLaundry

Popular amenities for Key West fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-Friendly apartment accommodation

5 out of 5 average rating, 8 reviews

Apartment in Islamorada

Ocean View Duplex Penthouse | Pool | Vista Two

Getting aroundTVLocation

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 and Hyatt Beach House

FamilyBeachComfort

5 out of 5 average rating, 21 reviews

Apartment in Marathon

Waterfront Escape | Pool, Tiki, Breakfast & Marina

AmenitiesKitchenAccuracy

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

ComfortAmenitiesSleep quality

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

FamilyComfortCleanliness

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

Check-inCleanlinessCheckout

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

PoolBathroomLocation

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, 1,377 reviews

Standard 1 Bedroom King Suite with Balcony

ParksBikingComfort

Fitness-friendly condo rentals

A serene view of the marina is presented, featuring multiple boats docked along the water. The bright blue pool, surrounded by lush green palm trees, reflects the clear sky above. A white pergola frames the outdoor area, enhancing the coastal landscape.

4.97 out of 5 average rating, 98 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

BikingDecorView

5 out of 5 average rating, 36 reviews

Large sliding glass doors provide a view of the boat basin and lush palm trees. The spacious living area features a comfortable sofa and ceiling fan, with tiled flooring that enhances the airy atmosphere. The outdoor patio showcases a dining set with chairs, inviting serene waterside relaxation.

Condo in Islamorada

Luxury condo with boat slip overlooking the bay

AccuracyBeachView

A waterfront view showcases a two-story building with a teal roof, framed by palm trees. Two boats are docked alongside the marina, reflecting on the gently rippling water under clear skies.

Condo in Stock Island

4.75 out of 5 average rating, 430 reviews

Grand Marina Suite - Poolside & Waterfront Condo

DecorIndoor spacesLayout

4.71 out of 5 average rating, 24 reviews

Salvador's Seclusion | Cozy Studio Retreat w/ Pool

BikingConditionQuiet

4.85 out of 5 average rating, 34 reviews

Key West's Crown Jewel

ConditionAmenitiesOutdoor spaces

4.59 out of 5 average rating, 106 reviews

Sunrise Suites Condo with Balcony - Shared Pool

Outdoor spacesQuietParking

4.72 out of 5 average rating, 236 reviews

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

BikingOutdoor spacesAccuracy

A shaded pergola is positioned within a landscaped yard, featuring a wooden swing. Surrounding palm trees and flowering plants create a vibrant setting, with the ocean visible beyond a white picket fence under a clear blue sky.

5 out of 5 average rating, 6 reviews

Hyatt Windward Point Key West- Two Bedroom

BikingComfortCleanliness

Fitness-Friendly Holiday House

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

ConditionCheck-inDecor

The spacious canal-front home is showcased from an aerial view, highlighting its private pool and lush palm trees. A dock with boat access extends into the water, while comfortable outdoor seating is positioned nearby, creating a relaxed atmosphere for guests.

5 out of 5 average rating, 36 reviews

Spacious lux home, private pool/spa, 80' dock

BikingBackyardIndoor spaces

5 out of 5 average rating, 82 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

BikingIndoor spacesTV

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

WalkabilityBreakfastIndoor spaces

A tranquil lagoon is seen, featuring clear, shallow waters that gradually deepen. Lush palm trees border the sandy beach area, providing shade. A Tiki hut is visible in the background, enhancing the serene outdoor setting under a partly cloudy blue sky.

Flipper's Lagoons

LocationAmenitiesCleanliness

New place to stay

Emerald Palms, Canal-Front, Dock, Gulf Access, Ma

4.88 out of 5 average rating, 8 reviews

Seaside Retreat: Waterfront Home with private heat

Outdoor spacesSleep qualityWalkability

A light green two-story house is surrounded by lush tropical plants. The front porch features white railings and is accessed by a set of stairs. Nearby parking is available, and sunlight brightens the exterior under a clear blue sky.