Villa vacation rentals in Islamorada

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Top-rated villa rentals in Islamorada

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Guest favorite

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 favorite

Villa in Marathon

4.95 out of 5 average rating, 123 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!

Superhost

Villa in Duck Key

4.81 out of 5 average rating, 36 reviews

Family Friendly Sunset Oasis!

Welcome to Driftwood Villa.This newly renovated 2 bed 1.5 bath luxury villa is located in the popular area duck key alongside of Hawks Cay Resort.Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including small kitchen appliances , silverware ,plates , cups , and pots. Linens and towels are also provided THIS PROPERTY DOES NOT HAVE ACCESS TO HAWKS CAY AMENITIES

Guest favorite

Villa in Key Colony Beach

5 out of 5 average rating, 24 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.

Superhost

Villa in Marathon

4.76 out of 5 average rating, 72 reviews

Villa 7075 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, NO pets.

Guest favorite

Villa in Key Largo

4.92 out of 5 average rating, 103 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 Marathon

5 out of 5 average rating, 6 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

4.91 out of 5 average rating, 226 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 Islamorada

4.9 out of 5 average rating, 10 reviews

Islamorada house next to sand bar. Lic # 24-0055

Relax with the whole family at this peaceful Angler's Reef boutique complex. Oceanfront community located at Mile Marker 85 has a beautiful community pool overlooking the Atlantic ocean. The community also offer kayaks, which can be launch from the private beach. This home has 2 bedrooms located on the 2nd floor with their private bathroom. The kitchen is fully equipped with stainless appliances, granite counters, 3 TVs & WiFi. The property has parking for 2 vehicles.

Guest favorite

Villa in Marathon

4.9 out of 5 average rating, 77 reviews

Villa in Paradise. Plunge pool. Middle of the Keys

Baja Breeze 🏝, a freshly updated, family-friendly, resort-style villa in the ♥ of the Keys. ♥ Please save Baja Breeze by clicking on the heart in the top right hand corner, this will help you find it again and share with others! 🛶 Waterfront canal view 🌴 Gated Resort Area 👙 Private spa pool 📍 Halfway between Key Largo and Key West ☀️ Outdoor dining/lounge area 🍳 Fully stocked Kitchen 📶 300Mbps+ Wifi

Guest favorite

Villa in Marathon

4.87 out of 5 average rating, 55 reviews

New Paradise On Sombrero Beach

Enjoy this BRAND NEW - 4/3, private pool and dock with room for up to a 40ft boat! This tropical getaway is in the heart of the Florida Keys. This beautiful and spacious villa is in Marathon, FL and is just one mile from the spectacular and famous Sombrero Beach. Sombrero Beach is the perfect place for a beach day with bathrooms, showers, a fishing pier, playground and beach volleyball.

Guest favorite

Villa in Duck Key

5 out of 5 average rating, 76 reviews

★Beautiful Gated Oasis★with private pool and patio

Enjoy a great family vacation with the conveniences of a modern home in this beautifully decorated gated house with private pool and patio, carport, 70" 4K Smart TV, high speed internet - 1,000 mbps, and fully equipped kitchen. Close to tropical activities and great restaurants. Relax, bond, and make new memories in the Florida Keys.