Villa vacation rentals in Islamorada

Find and book unique villas on Airbnb

Top-rated villa rentals in Islamorada

Guests agree: these villas are highly rated for location, cleanliness, and more.

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Guest favorite

Villa in Marathon

5 out of 5 average rating, 10 reviews

Harbor hideaway 50’dock 3Br/2Ba All amenities

VACA-23-42 is a charming villa that perfectly serves as your cozy retreat, featuring a private saltwater pool right by the water’s edge. There’s ample space available for your boat, trailer, and several vehicles. Enjoy our bicycles and kayaks during your stay. The property also boasts a tiki hut equipped with a commercial ice machine, grill, and a fish freezer for all your fishing needs. This unique getaway is conveniently situated near all local attractions, making your trip planning a breeze.

Guest favorite

Villa in Duck Key

4.95 out of 5 average rating, 86 reviews

Waterfront Island Escape with Private Plunge Pool

Come and relax in your own private plunge pool that overlooks a turquoise canal on the beautiful Duck Key. The outdoor living space is quiet and serene, making it a perfect place to unwind. Families and honeymooners alike can enjoy this island oasis. Centrally located at Mile Marker 61, Duck Key is just a short drive to Key West. Explore everything the Florida Keys have to offer or stay locally to enjoy world-renowned restaurants, fishing, snorkeling, and diving. The opportunities are endless.

Guest favorite

Villa in Marathon

4.95 out of 5 average rating, 135 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Guest favorite

Villa in Duck Key

4.91 out of 5 average rating, 46 reviews

Villa 5028 on Duck Key BOAT SLIP available

Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

Top guest favorite

Villa in Key Colony Beach

5 out of 5 average rating, 27 reviews

Canal/Dock - Cabana Club - Pickleball - Remodeled

Keys Hideaway - Remodeled, clean 2/2 villa w/ 30ft dock. We boast one of the largest and most private canals in KCB. Enjoy the nightly walks along 7th Street's boardwalk that runs along the canal. Directly across the street are the following amenities: 10 Pickleball Courts 9-Hole Golf Course Walk to the beach, pool and Tiki bar at the Cabana Club (membership included with the rental). You can either relax and grill on the back patio and/or walk to a local restaurant/bar on the waterfront.

Guest favorite

Villa in Key Largo

4.95 out of 5 average rating, 66 reviews

Oceanfront/2 Pools/Lagoon/Tennis/Picketball/Marina

This Ocean Front Key Largo Villa is located on MM 100 in a secure gated community with 24 hr security. This two-story, 3-bed, 3-bath 2035 sq ft. Villa overlooks the Marina and the Atlantic Ocean! Inside you’ll find tasteful furnishings with TV in each room, Outdoors you’ll enjoy many amenities at the Yacht Club, two heated pools, tennis, pickle-ball, playground, fire pit, a salt water lagoon with a sandy beach and diving board. Fishing, sunset and sunrise views at the end of the Jetty.

Guest favorite

Villa in Key Largo

4.92 out of 5 average rating, 113 reviews

Kawama Yacht Club and Molasses Reef Marine

Vacation in paradise. Beautiful sunsets. Swim at the salt water lagoon or at the beach plus two pools. Our villa is fully equipped, 3 bedrooms wish tv and 3 full baths First floor: garage, 1 bedroom, full bathroom, game room, pool table, bar, family room with TV, and terrace with barbecue and swing. Second floor 2 bedrooms and 2 full bathrooms, fully equipped kitchen and living a big TV, outside balcony with outdoor furniture . Tennis courts available. Optional 24' ft boat slip available.

Guest favorite

Villa in Duck Key

4.95 out of 5 average rating, 135 reviews

Beach House - Kayaks & 2/2.5 Villa

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

Guest favorite

Villa in Marathon

5 out of 5 average rating, 7 reviews

Villa Marlin - Perfect Vacation in Florida Keys

Spacious house, newly built with a private outdoor pool in the beautiful Florida Keys. This is the perfect location for boating enthusiasts. There is space for both parking and boat trailers. An exclusive ramp is a block away (30-second drive or 1-minute walk), leads to Gulf of Mexico, and 10 minutes to the Atlantic Ocean. A pool heater is provided for free for renters during the Winter. Outdoor pool shower included. Barbecue gas always provided. Games include corn hole, domino, billard.

Superhost

Villa in Marathon

5 out of 5 average rating, 9 reviews

Marlin House (52): Luxury 3/3 Villa w/ Dock, Pool

Welcome to the Marlin House. This 3 bed 3 bath luxury villa is located in the gated community of Indigo Reef. Immediate boat access to the Gulf and Ocean. 31' dockage incl. You'll appreciate the professionally decorated open floor plan that expands through the gourmet kitchen, family room and onto the outdoor lanai. Three private bedrooms, each with decks. Enjoy happy hour and grill your catch as you watch the sunset! Free WiFi, Parking & Dockage Contact owners 24/7 for any assistance

Superhost

Villa in Marathon

4.92 out of 5 average rating, 12 reviews

Florida Keys Wellness Gem Tranquility & Activity

Enjoy yourself in the Florida Keys in this spacious, 3 BR, 3 baths condo in Marathon, right on the Gulf coast! TWO private hot tubs ensure you can star gaze on the rooftop or come home from a run or bike ride and go straight for a hot soak! The view from the rooftop is amazing, rooms are spacious and clean. Add the fully equipped kitchen, washer & dryer as well as fresh sheet service and so much more. This home also has a shared pool and beach area and two private parking spots.

Guest favorite

Villa in Marathon

4.85 out of 5 average rating, 41 reviews

(#4)Beautiful 4 Bed 3 Bath Pool Home w Free Dock

#4: A WAVE💦 FROM IT ALL (Partial Ocean View Property-approximately 150 ft from beach entrance)🌸 Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming Pool 🤿and BBQ Patio. Includes Private Guest Beach🏖 with Kayaks and Paddle boards and Private powered ⛵Boat Dock right on the Gulf of Mexico! 🌅🥂 Kick back and completely🍷 relax in our Beautiful and 🍹comfortable home! Perfect for 🍻Adults and kids of all Ages!

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What guests are saying

Sunset Villa in Duck Key

4.75 out of 5 average rating, 142 reviews3 days ago

I had a wonderful stay at Gabriel’s house! The home was very welcoming and spotlessly clean, with an absolutely amazing view. Gabriel was a fantastic host—super friendly and always quick to respond to any questions. I would definitely recommend this place to my friends and would love to stay here again!

Villa in Marathon

What guests are saying

Isla Acai: Waterfront Htd Pool, Dock, Walkable

4.5 out of 5 average rating, 4 reviews6 months ago

We really enjoyed our stay at this villa. The location was great. The villa is bright and clean. We enjoyed the dock a lot. We saw many types of fish and even manatees at the dock.! We used the gas grill 2 nights and that was an amazing amenity to have! The villa is close to grocery stores and a good midway point on the island to see many things and visit great snorkeling spots. We enjoyed a fishing charter nearby and caught tuna! We also did a snorkeling trip and ended our stay with a private sunset charter by a local family.

Villa in Islamorada

What guests are saying

Waterfront villa for families * Family friendly*

4.83 out of 5 average rating, 99 reviews2 weeks ago

We had a fantastic stay at this Airbnb! The space was spotless, well-maintained, and exactly as described in the listing. It had everything we needed for a comfortable and relaxing visit. The host was also very responsive and made check-in super easy. The neighborhood was quiet and safe, and we really appreciated all the thoughtful touches throughout the home. We’d definitely book again the next time we’re in the area. Highly recommend!

Villa in Duck Key

What guests are saying

Tranquil Ocean View Villa with relaxing tiki

5 out of 5 average rating, 6 reviews12 months ago

We loved this place. It looks brand new and has a beautiful setting on a canal looking out to the ocean. Very close to Sombrero Beach and less than a 10 minute drive to all of the best restaurants in Marathon. Perfect location and great house - highly recommended.

Villa in Marathon

What guests are saying

Key Lime Cottage - Lovely Duck Key Villa, Dip Pool

4.53 out of 5 average rating, 15 reviews4 months ago

Beautiful little townhome on duck key! I had a medical conference, and I walked to it every morning. Very convenient. We would stay again. Our only complaint was that the larger bedroom bed was so uncomfortable. I woke with severe back pain first 2 nights. My husband and I then slept in the twin beds in the other bedroom which were much more comfortable! Other than that, no complaints. It was December, so dipping pool of course was cold, but it would be so nice to have during a summer stay! Quick responses from the owner or manager! We had enough trash bags, toilet paper and paper towels for 2 people for our 6 day stay, which was very nice! Kitchen is fully functional and full size fridge!

Villa in Marathon