Holiday rentals in Windley Key

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Top-rated holiday rentals in Windley Key

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Guest favourite

Boat in Tavernier

4.91 out of 5 average rating, 375 reviews

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Guest favourite

Apartment in Tavernier

4.9 out of 5 average rating, 295 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Guest favourite

Home in Islamorada

4.93 out of 5 average rating, 46 reviews

Beautiful Anglers Reef - 2/2.5 - Pool+Marina+Beach

Slip available for rent 6/22/24 & 7/20/24. DM for details Sat - Sat preferred, inquire as needed Awesome family get-a-away in beautiful Islamorada. The Oceanfront pool is serene! The gated community is an immaculately kept flora fauna setting. Located in walking distance to swim with the dolphins at Theater of the Sea and local restaurants and bars. Anglers Reef is perfect for boaters, kayaker's, foodies, honeymooners, couples, snowbirds or anyone that wants to experience the Florida Keys.

Top guest favourite

Home in Key Largo

4.99 out of 5 average rating, 190 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Superhost

Boat in Marathon

4.8 out of 5 average rating, 276 reviews

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

Top guest favourite

Home in Islamorada

4.97 out of 5 average rating, 196 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Superhost

Apartment in Tavernier

4.84 out of 5 average rating, 227 reviews

Toes in the Sand - 2 Bedroom Condo Sleeps 4

2-bedrooms, 2 full baths located on the 4th floor with ocean views. This condo has a beach, viewing pier, rentable boat slips, & boat trailer storage, café and a very large heated pool with a bar and gated entry with 24 hour security! Perfectly located between Key Largo and Islamorada, close to Pennekamp State Park, Harry Harris State Park, popular restaurants on the water, and the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer at your footsteps.

Top guest favourite

Boat in Islamorada

4.93 out of 5 average rating, 351 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Top guest favourite

Townhouse in Islamorada

5 out of 5 average rating, 12 reviews

Panoramic Oceanside Luxury, Dockage & Gameroom

🌴 Paradise Palms - Guest Favorite 🌴 Indulge in luxury & exclusivity at Paradise Palms, a newly built oceanfront gated home with dockage and panoramic views. This three-story retreat blends modern design with tropical charm. Enjoy breathtaking sunrises, unforgettable sunsets, and unmatched ocean views from nearly every room—you won’t find a home closer to the water! We believe in offering the best and are committed to ensuring your stay is nothing short of exceptional.

Guest favourite

Villa in Islamorada

5 out of 5 average rating, 36 reviews

Anglers Reef Islamorada

2 Bed & 2.5 Bath Villa in Anglers Reef .Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, upstairs balcony. Spacious villa, one of the biggest 2 bedroom villas in the community. Cherry hardwood floors, kitchen granite counter tops, boat slip can be reserved for additional fee, if available .

Guest favourite

Cottage in Key Largo

4.89 out of 5 average rating, 359 reviews

Cottage By The Sea

Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Be sure to meet Frank out 120 pound Sulcata tortoise.Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals

Top guest favourite

Townhouse in Islamorada

4.98 out of 5 average rating, 58 reviews

Peacock Shores Islamorada - Vacation On The Beach!

The ocean is your front yard at this modern, luxurious townhome hidden away in a small, private seaside community. Enjoy the pool, the beach, the dock and the peacocks! Walk to restaurants or cook at home on your private grill. We are work-from-vacation-home friendly with desk, chair, hi-speed wifi. Amazing fishing, boating, sightseeing, relaxing and dining experiences are all around you here, come visit and invent your perfect vacation!