Fitness-friendly holiday rentals in Big Pine Key

Refreshed & Elevated Indigo Reef Luxury Villa 15,

Sunset Villa is a Lux 3 BD, 2.5 BA marina home and a 31 ft dedicated boat slip located in the most exclusive townhome village on the island of Marathon in the Florida Keys. Newly remodeled to a casual coastal elegance by a professional designer, this private home shines. Sunset Villa has everything for a perfect island vacation: resort pool, 31 ft boat slip, gym, on site parking, lush grounds, and a designer villa. We also provide access to a private boat ramp and parking at a location closeby.

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

Waterfront 6BR Luxury Retreat w/ Pool & Dock

Welcome aboard Captain's Retreat, your 6BR/5BA tropical paradise in Marathon with 80 feet of dockage for up to 3 boats! I expanded from our popular Captain's Quarters to create this ultimate family compound with fast ocean access. Cruise the Atlantic on our premium Hobie kayaks, challenge family to shuffleboard by the heated pool, or rack 'em up in the billiards room – there's something for every generation in your crew! 🏊‍♂️ Luxury heated pool & spillover spa ⛵ Private 80ft dock with Hobie pe

*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.

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.

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

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.

Luxury Waterfront Suite w/ Marina, Pool, Tiki Bar

Welcome to the Bashful Barracuda—the brand-new 1BR/1BA luxury Waterfront Suite overlooking beautiful Boot Key Harbor. Enjoy peaceful water views, boat slips just outside your door, and a resort featuring a sparkling pool, a lively Tiki Bar, chef-crafted restaurant, and on-site Marina— located in the heart of the Florida Keys making it the perfect place to explore the Islands or just relax and enjoy this piece of paradise.

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.

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

Suntastic - Indigo Reef 11 - 3 BR & 31' Boat Slip

License # VACA-21-206 - Indigo Reef Villa 11 with Boat Slip #6. Classic Keys furnishings, a fully stocked kitchen, a private patio overlooking the Gulf of Mexcio, and plenty of space to ensure privacy and comfort for the entire group; all qualities of the Indigo Reef resort's villa 11. Your personal in-unit WiFi connection allows you to share the Florida fun with all of your friends.