Fitness-friendly holiday rentals in Key West

Wake Up On the Water with Southernmost Serenity

Experience life on the water with a unique Key West stay aboard a comfortable yacht docked at the beautiful Perry Hotel & Marina on Stock Island. Enjoy ocean breezes, waterfront sunsets, and resort-style amenities while staying just minutes from the energy of downtown Key West. The boat offers a comfortable and inviting space designed for relaxing after a day exploring the island, chasing sunsets, or enjoying life on the water. Inside, you’ll find cozy sleeping accommodations, thoughtful essentials, and everything you need for an easy, memorable Key West stay. *Please note that the sofa bed in the salon is actually a convertible dinette. Additional details below. Boat Features - Comfortable sleeping areas (two bedrooms that sleep four comfortably, plus a convertible dinette in the salon that will sleep another 1-2 guests comfortably) - Induction cooktop for simple meals - Microwave - Electric toilets for added comfort - Cozy interior living space - Unique waterfront stay experience (Please note: for safety, the propane powered oven in the galley has been unhooked and is not functioning.) -Propane grill on the sundeck for grilling while watching the historic Key West sunset Perry Hotel & Marina Amenities - Private marina showers and bathrooms to compliment the shower and bathrooms on the boat itself - Two outdoor resort-style pools - 24-hour fitness center - Yoga classes - On-site dog parks - Water sports and excursions (jet ski tours, fishing charters, sunset sails) - On-site laundry Dining & Drinks Nearby - Matt’s Stock Island Kitchen & Bar - Salty Oyster Dockside Bar & Grill Getting Around - Complimentary shuttle to and from Old Town Key West every half hour - Easy access to Duval Street, beaches, restaurants, and nightlife - Valet or self-parking available at the marina (self-parking is free) Whether you’re visiting for sunshine, boating adventures, or the vibrant Key West atmosphere, this marina stay offers a fun and memorable way to experience the island. Come live like the Songs You Know By Heart

Accuracy · Location · Indoor spaces

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

Parks · Access · Air conditioning

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.

Condition · View · Sleep quality

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

Biking · Pool · Beach

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.

Biking · Walkability · Air conditioning

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.

Biking · Decor · Access

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.

Biking · Laundry · Nearby

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.

Biking · Sleep quality · Nearby

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.

Nearby · Pets · Location

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.

Biking · Cleanliness · Parking

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!

Biking · Decor · Wi-Fi

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

Biking · Beach · Access