Holiday rentals with a hot tub in Summerland Key

5 out of 5 average rating, 5 reviews

Home in Key Colony Beach

Huge Swim Spa~ Incredible Special Fall Pricing

3 Bedroom~ 2 Bath Duplex With Outdoor Solar Shower, on a Deep Water Canal in Key Colony Beach. Near The Vaca Cut Makes For Easy Access To The Gulf Of Mexico or Atlantic Ocean. Boat Dockage for up to a 34' Boat. Golf Course, Pickle Ball~Tennis Courts, and Great Playground. We have a Large Swim Spa in The Private Garden, Arcade Game Room~Ice Maker, Paddle Board, 2 Kayaks, 4 Fishing Rods & Bait, Margarita Machine, Outdoor Shower. Cabana Club Membership With Free Beach/ Ocean Access & Huge Pool.

4.89 out of 5 average rating, 18 reviews

Boaters delight! 1 min to open water, Dock & Beach

Inquire for monthly discounts. The happy house 339 at ghee mail. Quaint and charming home nestled in the Florida Keys. Secluded single family property with open water access. Private Dock, Beach, kayak launch area with kayaks and bikes available to use. Very private tranquil location. See manatees/fish swimming by. Enjoy endless sunsets from the front porch. Fantastic views from every room in the house. Beds: 1 King bed, 2 twins, 2 trundle Marathon Vacation Rental License#. VACA-22-375

4.92 out of 5 average rating, 50 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

Meet Casa Kokomo, a laid-back luxe retreat in the Florida Keys. This home has a 7-night minimum stay requirement and offers the perfect blend of salt life and relaxation. Plenty of natural light enters through the large windows in the sunroom, creating a warm ambiance. For those who enjoy the outdoors, step out to the backyard for fresh ocean air, unwind in your private hot tub, or visit nearby sandbars. Property includes a 32-foot private dock with direct ocean access. Max boat size 30Ft.

4.67 out of 5 average rating, 411 reviews

Apartment in Key West

Sunshine Suite Condo Enjoy outdoor Hot tub & Pool

Our Private condo 2 bedrooms & 2 bathrooms is for you to Enjoy your Vacation. Full equipped kitchen King sized beds in each room and 1 Queen-sized pull out sleeper sofa-bed in the living room. Family friendly Free WiFi Free parking !NO SMOKING in the apartment - on the balcony only with the closed balconies doors! NO SHOES IN THE HOUSE NO FOOD IN BED NO OIL/ OILY SKIN in BED NO Make-up wash off with our towels NO auto tan and etc wash off with our towels Late check out fee: $50/hour

4.75 out of 5 average rating, 24 reviews

Sunset Views, Pool and Dock

Beautiful two bedroom two bath single family home with pool and spa with dock right on the water! Enjoy the beautiful sunset and bay views from our dock, deck or pool! Bring your boat and bathing suits and enjoy this wonderful home in the Heart of the Florida Keys! Pool heat is an additional fee Kayaks and golf carts rental available upon request Saturday to Saturday during busy months except September and October. And you can always ask 7 night minimum no exceptions VACA-22-34

4.92 out of 5 average rating, 137 reviews

Marathon Star - home with hot tub

Completely renovated 3 bedroom house in Marathon. Conveniently located near the Florida Keys Aquarium Encounters and the Marathon Lady. Enjoy a private hot tub and outdoor grill after a long day of Florida sunshine! Our home is not on the water but there is plenty of parking space for your boat trailer if needed. We hope our wonderful space becomes a great home away from home. ***Please see below for more information regarding hurricane season cancellation policy.

4.89 out of 5 average rating, 87 reviews

Home in Key West

Near Duval: Hot Tub, Sleeps 6, Top Location

Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.

4.64 out of 5 average rating, 50 reviews

Home in Cudjoe Key

Relaxing Cottage in Cudjoe

MANDATORY REGISTRATION FEE NOT INCLUDED. $125 DUE UPON ARRIVAL TO VENTURE OUT COMMUNITY. Venture out community offers many amenities including Heated Pool, Hot Tub, Basketball Courts, Tennis Courts, Marina, Boat Ramp, Private Convenience Store, Children's Pool, Bath Houses, Laundry Facilities, Fish Cleaning Station, Horseshoes, Ping Pong, Children's Play Area, Bocce Ball, 24 Hour Gated Security, Salt Water Swimming Area, Recreation Hall and Pickle Ball Court.

5 out of 5 average rating, 33 reviews

Oceanfront w/ Dock, Hot Tub & Secluded

Buchanan Keys Cottage Take a step back into “Old Keys” living. Once Upon A Tide; there was a sense of tranquility & peacefulness found throughout the Keys, like the one you will uncover when choosing to stay at this private, serene, 1/1 oceanfront cottage. Located on Grassy Key, this beautiful home is just 10 minutes from the City of Marathon. Far enough to be away from the hustle & bustle, but close enough to make a grocery/store run a “Keys breeze”.

4.82 out of 5 average rating, 28 reviews

Home in Key West

Casablanca Too ~Chicly updated home with hot tub

On the edge of Historic Old Town and tucked in a residential neighborhood, Casablanca Too is a great place to enjoy the fun, carefree vibe of Key West. This 1 bedroom/1 bath duplex was recently redesigned and will meet all your needs while away from home. THE PROPERTY: Enjoy fresh air and sunshine from your front porch or backyard hot tub at Casablanca Too. This unpretentious home has been beautifully updated and is ready to welcome you.

Top Guest favourite

5 out of 5 average rating, 17 reviews

*NEW!*Serenity Oasis~Kayaks~Bikes!~Hot Tub~Spa!

Welcome to your dream Serenity Oasis in the heart of the Florida Keys! This 3 BR sanctuary has been meticulously redesigned where every detail has been carefully curated to let you indulge in the ultimate vacation experience in paradise. From a bubbling jacuzzi hot tub under the stars, to kayak and bike adventures, foosball cornhole and popcorn machine for fun and laughter, spa like bathroom retreats, there's excitement in every corner!