Fitness-friendly holiday rentals in Big Pine Key

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

*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.

Palm - 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. Experience the charm of our recently renovated, one-of-a-kind two-bedroom beach bungalow, nestled right on the shore. Enjoy breathtaking ocean views from your private deck, relax on the sandy beach, and soak in the tropical ambiance. This family-friendly retreat offers the perfect setting to make you feel like you’re on your very own private island.

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

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.

Luxury 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 ft 2-bed luxury boat with island bright touches is tucked away from the crowds in a resort style marina while being just minutes from downtown Key West. Featuring indoor and outdoor spaces for living, dining, and relaxing, as well as hotel amenities such as a pool, 3 bars and restaurants, and a gym. Vacation differently on A Whim.

Waterfront luxury Villa (43) with sunset views and boat slip

This remodeled 3BR/2.5BA villa is pure paradise. Recent updates include a fully renovated second bathroom, as well as upgrades to the living room and kitchen. Just steps away, your private dock fits up to 35' (max 3' draft, boaters insurance required). The villa features a fully stocked kitchen, TVs in every room, and resort grills for your fresh catch. Sleeps up to 8 (fee for 7+). Note: Minimum weekly rental. All bedrooms and full baths are located upstairs and involve stairs.

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.

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.

Daily Housekeeping, Waterfront Suite, Pool, Marina

Welcome to Mellow Marlin—a brand-new 1BR/1BA luxury Waterfront Suite with stunning views of Boot Key Harbor. Step outside to your private boat slip, unwind by the resort’s sparkling pool, or enjoy the lively Tiki Bar and chef-inspired restaurant. With an on-site marina and a prime location in the heart of the Florida Keys, it’s the perfect spot to explore the islands or simply soak in the serene waterside atmosphere.

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.

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!