Villa vacation rentals in Islamorada

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.

Villa 5034 on Duck Key BOAT SLIP available

Boat slip available for an additional $100 per night. Ask about availability. This villa boasts breathtaking sunsets and is just minutes from watersports, charter fishing, waterfront restaurants, and local attractions, all while being surrounded by one of Duck Key’s most exclusive island neighborhoods with lush tropical landscaping. Duck Key is perfect for families or a serene couples retreat. Dine while watching spectacular sunsets from the rear deck, or explore the Middle Keys. No smoking/Pet

The Nest Villa & Marina in the heart of Islamorada

You will fall in love with the "Nest", a unique and peaceful villa in the heart of Islamorada with private sun terrace & stunning water views of Florida Bay. If you are seeking an unforgettable Keys getaway this is it! Bring your boat (or rent locally). Dock in our protected marina with launch ramp & on site trailer parking. Swim, snorkel & paddle in crystal waters directly from our jetty. World-class fishing and diving only minutes away. Take a short stroll to shops restaurants & a brewery!

Deep Blue ~ Waterfront Gem ~ Pool ~ Kayaks ~ Dock

Escape to the stunning Deep Blue, a 4BR 3BA waterfront retreat in the exclusive Key Colony Beach, Florida Keys. This expansive two-story estate offers the ultimate island getaway with its sophisticated design, luxurious amenities, and breathtaking water views from your private 112-foot dock. ✔ 4 Luxurious BRs ✔ Gourmet Kitchen ✔ Heated Swimming Pool & Spa ✔ Waterfront Yard (Fire Pit, BBQs, Games, Kayaks, Bicycles) ✔ 112ft Private Dock (Fishing Station, Water, Electricity) ✔ Smart TVs Throughout

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!

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

This oceanfront villa in the Florida Keys offers stunning views of the Marina and Atlantic Ocean, with 3 bedrooms, 3 bathrooms, and 2,035 square feet of tastefully furnished living space. Guests enjoy private TVs in each room and resort-style amenities, including two heated pools, tennis, pickle-ball, a playground, fire pit, and a 3-acre saltwater lagoon with a beach and diving board. A golf cart is available for scenic trips to the point (jetty), for fishing and watching sunrises or sunsets.

Top guest favorite

Guest favorite

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.

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! One private hot tub and one private plunge pool ensure you can star gaze on the rooftop or come home from a run or bike ride and go straight for a 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 two private parking spots.

Top guest favorite

Guest favorite

Beach House | Waterfront Villa | Kayaks

Wake up to beautiful water views and the laid-back charm of Duck Key. This beautifully renovated waterfront villa offers a relaxed coastal setting, comfortable living spaces, and inviting outdoor areas made for morning coffee, sunset views, and evening cocktails. Ideally located in the heart of the Florida Keys, it’s a perfect home base for boating, fishing, snorkeling, beach days, and waterfront dining, with Marathon, Key West, Islamorada, and other Keys favorites within easy reach.

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!

Top guest favorite

Guest favorite

Duck Key Waterfront Villa w/Kayaks, near 2 Marinas

Welcome to Crystal Waters Cay, an immaculate 2BR/2.5BA villa steps from the water inside the Hawks Cay Resort area and marina! Our unique hotel designation means 1-night stays are welcome—perfect for a quick Keys escape. Enjoy two private upstairs suites, free tandem kayaks, and plenty of unassigned first-come parking. Walk to public resort highlights like the 5-star dining at Salt + Ash, waterside eats at Angler & Ale, the marina, gym, and spa. Fixed cleaning fee applies.

Oceanfront Resort W/Indoor Pickleball - Speakeasy!

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Key Largo's most upscale oceanfront community. The area has the distinction of being Key Largo's newest oceanfront gated destination, with some of the most unique amenities in all of the keys. It caters to those who simple desire the very best in luxury accommodations. Unique amenities include a Speakeasy Themed Rec. Area.