Villa holiday rentals in Islamorada

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Top-rated villa rentals in Islamorada

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Guest favourite

Villa in Duck Key

4.97 out of 5 average rating, 78 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 favourite

Villa in Marathon

4.95 out of 5 average rating, 126 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 favourite

Villa in Key Colony Beach

5 out of 5 average rating, 25 reviews

Keys Hideaway Completely Remodeled w/ Cabana Club

Completely remodeled, clean 2/2 villa with 40ft dock - bring your boat up to 50ft. Great view of both the canal and causeway from your back yard. Directly across the street are the following amenities: 9-Hole Golf Course Pickleball Tennis Basketball Children’s Playground Horseshoe Bocce Ball 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 favourite

Villa in Duck Key

4.95 out of 5 average rating, 40 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.

Guest favourite

Villa in Marathon

5 out of 5 average rating, 9 reviews

Waterfront Home w/Dock, Pool, Bikes & SO MUCH MORE

Looking for the perfect home for your next Florida Keys vacation? Our Waterfront home with over 30 feet of dock space is Just a short boat ride out to open water for a day of fishing, snorkeling, or cruising around. Our home features your own private dock & private pool... complete with chaise lounges, outdoor dining, gas grill, Adirondack chairs, fish cleaning station, bait freezer & so much more! Lastly, everyone is sure to enjoy water views & sunsets from our balcony that never disappoint.

Guest favourite

Villa in Key Largo

4.95 out of 5 average rating, 59 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 favourite

Villa in Key Largo

4.92 out of 5 average rating, 104 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 favourite

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

4.91 out of 5 average rating, 272 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Superhost

Villa in Marathon

4.96 out of 5 average rating, 26 reviews

Sombrero Beach house with private dock and pool

Casa MarBella @ Sombrero Beach offers plenty of indoor and outdoor space. Enjoy our beautiful pool with flowing waterfall which can be heated for an additional fee. Please inquire before booking. Dock on deep water canal with shore power and commercial ice maker in the garage. Weber gas grill, convenient outdoor counter with built-in ice chest and sink. Large yeti cooler with wheels, paddle board, 12ft fishing kayak, beach tricycle, pedal boat and 4 bikes.

Guest favourite

Villa in Duck Key

5 out of 5 average rating, 65 reviews

Duck Key *Bliss* Private Pool & Patio

Enjoy a great family vacation in this comfortable cozy home located in The Sanctuary, an exclusive gated area of Hawks Cay Resort. This home offers a private swimming pool and patio in a lush tropical setting, large Smart 4K TV's, high speed internet - 1,000 mbps, and fully equipped kitchen. Close to great restaurants and fun tropical activities. Relax, unwind, bond, and make new memories at the Florida Keys.