Fitness-friendly holiday rentals in Big Pine Key

5 out of 5 average rating, 60 reviews

A tray displays two coconut cups filled with a refreshing beverage, each adorned with a pink paper umbrella. Slices of watermelon are arranged on a plate beside the drinks. The vibrant blue water of the heated pool glistens in the sunlight, surrounded by tropical greenery.

Home in Marathon

Luxury Boating Paradise+Pool+Sailing Kayaks

Captains Quarters, Your 4BR Waterfront Oasis on a deep-water ocean canal. This meticulously remodeled home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ Luxury heated pool & spillover spa ⛵ Private 75ft dock with sailing kayaks for ocean adventures 🕹️ Epic game room with Golden Tee, Pack Man, foosball table, Ping Pong & Infinity Game Table 🍳 Outdoor patio with BBQ grill & waterfront dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

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, 167 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

4.81 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)

Home in Upper Sugarloaf Key

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

4.94 out of 5 average rating, 105 reviews

Lighthouse - Beach Houses Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings.

4.81 out of 5 average rating, 97 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.

4.89 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.

5 out of 5 average rating, 8 reviews

A covered porch features a wooden deck with several outdoor seating options. Palm trees sway gently in the background, overlooking a marina with docked boats and lush greenery lining the waterfront. The sky is clear with a bright sunlit atmosphere.

Townhouse in Marathon

Waterfront Villa (21) w/ sunset views & boat slip

This spacious 3BR/2.5BA Villa at Indigo Reef Marina Homes offers sunset views over the Gulf, a private dock (max 35’, 3' draft, no overhang, boaters insurance required), and easy access to parking, a quiet pool, and a gym. 75” TV with HBO. Sleeps up to 8 (fee for 7+ guests). Pet-friendly ($350 fee per pet). No smoking. (Note: bedrooms and full baths are located on the second floor of the Villa. Minimum weekly rental.)

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.

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, 154 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 fitness-friendly rentals in Big Pine Key

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

5 out of 5 average rating, 5 reviews

A spacious living area features large glass doors that open to reveal ocean views. The comfortable seating arrangement includes a light-colored sofa and a wooden coffee table. Natural light floods the room, creating a bright and inviting atmosphere. A dining area is visible in the background.

Flat in Islamorada

Ocean View Duplex Penthouse | Pool | Vista Two

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.

4.9 out of 5 average rating, 83 reviews

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

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.

4.67 out of 5 average rating, 3 reviews

Welcome to Your Tropical Key West Island Getaway

5 out of 5 average rating, 3 reviews

A tranquil pool area features lounge chairs arranged around a crystal-clear pool. Palms sway gently nearby, and a tiki bar with a roof can be seen in the background, overlooking calm waters. The sky transitions to a soft blue as evening approaches.

Flat in Marathon

Marathon Studio on Lovely Gulf Front Resort

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 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.

Flat in Marathon

4.61 out of 5 average rating, 912 reviews

Standard 1 Bedroom King Suite with Balcony

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.

The Cat Island Suite | Beautifully Renovated w/ Po

The modern building is designed with balconies overlooking a serene pool area. A turquoise pool is bordered by lounge chairs and palm trees, creating a refreshing outdoor space. The backdrop features a clear sky and a sandy waterfront, enhancing the tranquil ambiance.

4.91 out of 5 average rating, 34 reviews

Oceanfront Condo in Key West

Fitness-friendly apartment rentals

The living area features a light-colored sofa and a wooden coffee table, complemented by a flat-screen television. A kitchen bar with tall blue stools is visible in the background, along with refreshing aqua-colored walls that enhance the spacious atmosphere.

4.54 out of 5 average rating, 143 reviews

Cozy 2BR 3rd-Floor | Pool | Dog Friendly

A refreshing outdoor pool area is surrounded by palm trees under a bright blue sky. A poolside cabana with a green roof provides shade. The well-maintained pool deck offers ample space for relaxation and sunbathing.

4.67 out of 5 average rating, 96 reviews

Free Parking, Pool, & Pet Friendly - The Trinidad

5 out of 5 average rating, 29 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.

Apartment in Islamorada

Luxury condo with boat slip overlooking the bay

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, 38 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

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 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

5 out of 5 average rating, 17 reviews

The exterior of a twin home is depicted, showcasing a welcoming entryway with a landscaped front yard. A paved path leads to the entrance, framed by palm trees and vibrant foliage, while a spacious balcony extends over the ground floor.

Home in Key Colony Beach

Welcome to the Ocean Nest in Key Colony Beach, FL

A well-manicured exterior showcases a welcoming entrance framed by palm trees and tropical landscaping. A path of laid bricks leads to the front door, while a central fountain adds a tranquil focal point in the soft morning light.

Home in Key Colony Beach

4.6 out of 5 average rating, 35 reviews

Waterfront Oasis with Boat Dock & Pool!

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, 26 reviews

Funky Chicken Cottage with Shared Pool in Paradise

A two-story townhome is depicted, showcasing a light-colored exterior with white railings on the porches. Lush tropical landscaping surrounds the fenced property, with green foliage and colorful flowers visible. A paved pathway leads towards the entrance, framed by palm trees.