Villa holiday rentals in Islamorada

A serene waterfront scene is depicted, featuring paddle boards laid along a grassy area beside a concrete pathway. Palm trees and a sunset over the water contribute to the natural beauty, while boats are visible in a nearby dock.

4.83 out of 5 average rating, 12 reviews

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!

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

4.95 out of 5 average rating, 147 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!

A circular table is positioned on a covered deck, accompanied by four lounge chairs. The view extends to the calm waters beyond, framed by green trees on the coastline, under a clear blue sky. Ceiling fans hang above, providing a cooling breeze.

4.83 out of 5 average rating, 104 reviews

Villa 5023 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.

A serene beachfront area is presented with several white lounge chairs facing the tranquil blue waters. Rocky shoreline and greenery outline the space, creating a peaceful environment for relaxation.

4.92 out of 5 average rating, 118 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.

A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.

4.96 out of 5 average rating, 168 reviews

Beach House - Kayak 2/2.5 Villa - OS Slip/Ramp/Pkg

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.

A private hot tub sits on the rooftop terrace, surrounded by a white railing. Lush greenery fills the foreground, while a view of the Gulf coast extends towards the horizon under a clear blue sky.

4.9 out of 5 average rating, 20 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.

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

4.9 out of 5 average rating, 472 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!

A two-story structure with a light-colored exterior is framed by well-maintained greenery. The front porch features a railing and is flanked by palm trees, creating a welcoming entrance. Large windows allow natural light to enter the home.

4.9 out of 5 average rating, 21 reviews

Islamorada house with best location. 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.

An open-concept living and dining area is showcased, featuring a large wooden dining table set for several guests. A comfortable woven sofa is positioned nearby, with a stylish floor lamp providing light. Natural light floods the space through numerous windows, enhancing the warm ambiance.

4.61 out of 5 average rating, 18 reviews

Gull's Nest #36 4BR Key Largo Villa w/ Beach &

Discover a serene vacation rental where luxury meets tranquility. Ocean Residences offers modern design, a secluded retreat vibe, and access to the exclusive amenities of Playa Largo Resort & Spa, including pools, dining, and beachside relaxation (wristband required). Pet-friendly with a stunning clubhouse and Atlantic views, this destination ensures unforgettable memories. Complimentary shuttle service makes exploring effortless. Book your ultimate getaway today!

An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.

4.88 out of 5 average rating, 115 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

The open-concept living area presents a spacious layout with a kitchen featuring a dark granite countertop and stainless steel appliances. A dining table accommodates several chairs, while comfortable seating is visible in the living room area. Large windows allow natural light to fill the space.

4.84 out of 5 average rating, 116 reviews

MODERN OCEANFRONT CONDO! OCEAN VIEWS! 2 KING BEDS!

You have just discovered one of the most unique properties in the heart of Key Largo. This OCEAN FRONT condo is located inside Kawama Yacht Club, a beautiful Hawaiian Island style resort that is situated along the southern border to the most popular park in all of the Keys, John Pennekamp National Underwater Park. Everything you could ever imagine making your Florida Keys vacation complete can be found here.

A charming two-story villa is framed by swaying palm trees against a bright blue sky. Lush greenery borders the pathway leading to the entrance, which features a porch with round windows and white railings, emphasizing the inviting exterior of the residence.

4.98 out of 5 average rating, 43 reviews

Seas the Keys Getaway with plunge pool/spa

Waterfront Spa Villa with Private Plunge Pool/spa, located in beautiful Hawks Cay situated conveniently between Marathon and Islamorada in the Florida Keys. Enjoy world-class fishing, diving & snorkeling, boating adventures and more. Swim with Dolphins, visit the Dolphin Research Center or spend the day at a tropical adventure park, all just minutes from your front door!

Popular amenities for Islamorada villa rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Private villa rentals

5 out of 5 average rating, 11 reviews

Isla Guava: FREE Boat Dockage Sept-Oct Only!

A modern oceanfront clubhouse is illuminated at night, featuring spacious outdoor seating and a swimming pool surrounded by palm trees. The serene water reflects the evening sky, enhancing the tranquil ambiance of the area.

4.68 out of 5 average rating, 19 reviews

Tranquility #19 Luxury Villa by the Ocean | Pool

A private outdoor terrace is shown with wooden flooring and a large ceiling fan. Two white chairs face a stunning sunset over lush greenery, with soft light illuminating the scene. The balcony railings feature a classic design, enhancing the serene waterfront view.

5 out of 5 average rating, 5 reviews

Bayberry Key: FREE Boat Dockage Sep-Oct Only!

The villa is set alongside a tranquil waterway, featuring a private pool surrounded by lounge chairs. A tiki hut and picnic area are visible, adjacent to a landscaped yard. The property showcases a two-story structure with balconies, offering a lush tropical ambiance.

4.67 out of 5 average rating, 6 reviews

Isla Acai: FREE Boat Dockage Sep-Oct Only!

4.76 out of 5 average rating, 25 reviews

Twilight #32 Key Largo 4BR Villa | Pool,

A spacious living area features a comfortable gray sofa with decorative pillows, accompanied by a natural wood coffee table. A large television is mounted on a light wall, while a dining area with white chairs is visible in the background.

4.78 out of 5 average rating, 124 reviews

Waterfront villa for families * Family friendly*

4.86 out of 5 average rating, 7 reviews

Villa 5008 on Duck Key - Boat Slip Available

A tranquil canal scene is displayed, featuring wooden docks lined with boats. Lush greenery surrounds the waterway, contrasted by clear blue skies. The inviting area suggests accessibility for water activities such as snorkeling and scuba diving.

Spacious Villa w/ Boat Slip

Luxury villa rentals

A spacious dining area features a long wooden table paired with matching benches. Bright artwork adorns the white walls, while a chandelier hangs above. Large glass doors open to a view of the outdoor space, allowing natural light to fill the room.

5 out of 5 average rating, 13 reviews

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

A bright and spacious living area features a large dining table with wooden chairs and a central coffee table. Soft seating is arranged around a sliding glass door that opens to the outdoor patio. Decorative curtains frame the windows, enhancing natural light.

4.94 out of 5 average rating, 100 reviews

Waterfront Island Escape with Private Plunge Pool

A spacious outdoor area features a private pool surrounded by a wooden deck. Loungers invite relaxation under the shade of palm trees. The home, with two stories, showcases a covered patio equipped with dining furniture, complemented by lush greenery for added privacy.

4.96 out of 5 average rating, 26 reviews

Florida Keys Sanctuary

Two comfortable white Adirondack chairs are positioned on a wooden deck, overlooking a lush green lawn and palm trees. A canal with a boat can be seen in the background, completing the serene waterfront view.

5 out of 5 average rating, 5 reviews

Luxury Waterfront Villa, Marathon, Florida Keys

The two-story villa presents a light green exterior with multiple large windows, allowing natural light to enter. Elevated on stilts, ample space underneath offers shade, while the stairway leads to the main entrance. Architectural details emphasize a welcoming coastal style.

4.88 out of 5 average rating, 60 reviews

New Paradise On Sombrero Beach

A covered porch features four white Adirondack chairs positioned on a wooden deck. Lush green palm trees and landscaping provide a tropical backdrop, while a sparkling pool is visible in the distance, completing the serene outdoor setting.

5 out of 5 average rating, 12 reviews

Waterfront Villa (38) w/ sunset views & boat slip

4.86 out of 5 average rating, 44 reviews

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

4.93 out of 5 average rating, 76 reviews

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

Villa rentals with a pool

The living area features a comfortable gray sofa and a patterned armchair surrounding a wooden coffee table. Sliding glass doors provide access to the pool area, allowing natural light to fill the room and offering views of the lush greenery outside.

4.43 out of 5 average rating, 28 reviews

2BR water view with private pool, balcony & kayak

A sparkling pool is set against a backdrop of lush greenery and calm water. A hammock is suspended between palm trees, inviting relaxation. Surrounding the pool, well-maintained landscaping features vibrant plants and manicured grass, enhancing the serene outdoor space.

4.75 out of 5 average rating, 4 reviews

Villa Sombrero

A serene outdoor seating area features two white Adirondack chairs set around a round table. A glass of white wine and a cocktail sit on the table, accompanied by a book. A vibrant pillow with an anchor design rests on one chair, with views of lush greenery and the water beyond.

5 out of 5 average rating, 24 reviews

Waterfront Villa with Boat Slip

A serene marina scene is captured with boats moored on calm waters surrounded by lush palm trees. The sky displays dramatic clouds illuminated by the golden hues of sunrise, creating a peaceful coastal atmosphere.

4.78 out of 5 average rating, 69 reviews

Oceanfront Villa overlooking the Atlantic

A charming round villa is elevated on stilts, surrounded by lush greenery and colorful landscaping. The exterior features a spacious balcony with white railings, while bright orange doors add a pop of color. A sandy path leads to the entrance.

Florida Keys Resort Villa

A charming waterfront property is framed by lush palm trees. This open dwelling features a dock extending into the water, with colorful kayaks resting alongside. Reflections of the house and trees are visible on the serene water surface, evoking a sense of tranquility.

4.87 out of 5 average rating, 15 reviews

"Casa Sea Keys"-Oceanfront 10 Guests, Private Dock

An aerial view captures a marina community surrounded by lush greenery and clear blue waters. The scene includes multiple townhomes lined along the waterfront, with boat slips visible along the shoreline. A resort-style pool can also be seen in the center of the community.

5 out of 5 average rating, 4 reviews

Refreshed & Elevated Indigo Reef Luxury Villa 15,

A private pool is surrounded by a paved patio, featuring comfortable lounge chairs and large umbrellas for shade. Nearby, a hammock is suspended between two posts, and tropical greenery provides a natural backdrop. The area is well-lit by natural sunlight.