Villa holiday rentals in Islamorada

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, 146 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!

4.75 out of 5 average rating, 102 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.

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, 115 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, 156 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.

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, 395 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 house is set against a clear blue sky, featuring balconies and a light blue exterior. A wooden dock extends into tranquil water, with paddleboards and kayaks visible. A heated pool is surrounded by palms, offering a relaxing outdoor space.

5 out of 5 average rating, 5 reviews

Marathon Villa w/ Priv Pool/Dock

Marathon, Florida is in the middle of all the beauty and action of what the Florida Keys have to offer. Sombrero Beach is at a bike ride or walking distance. It offers complimentary parking, outdoor grilling, beach volleyball, children play area, and public restrooms. 40 foot dock offers guests the option to bring their boats or rent one. Our heated pool is a perfect way to soak up the tropical vibes. Kitchen is fully equipped. We are at walking distance to grocery store!

4.9 out of 5 average rating, 21 reviews

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.

Villa in Islamorada

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.

Aerial view of a modern vacation rental surrounded by water, featuring a sleek design and a spacious pool area. Lush greenery contrasts with the pristine waters, and palm trees line the property, providing a tropical ambiance. Nearby structures are visible in the background.

4.69 out of 5 average rating, 26 reviews

Hideaway #23 Key Largo 3BR Villa | Pool, Kayaks &

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!

A Tiki Hut is seen with a thatched roof and an inviting seating area featuring plush cushions. A large grill is positioned nearby, and a flat-screen TV is mounted above. The backdrop includes a large private pool surrounded by green foliage, creating a relaxed outdoor space.

5 out of 5 average rating, 9 reviews

Discount to Jan 31! Private Pool, Fun Amenities!

This property has everything! 4 bed, 3 bath, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and a natural landscape view across the canal! The dock is shared with the unit next door. One boat only is allowed. Limited parking. 2-3 cars with trailer max. The pool can be heated for a fee of $ 150 plus tax, processing. Prorated for longer stays.

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.

4.89 out of 5 average rating, 110 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.

4.83 out of 5 average rating, 111 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 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.

5 out of 5 average rating, 18 reviews

Florida Keys Sanctuary

Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool and loungers. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play and kids dishware.

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, 7 reviews

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.

Villa in Islamorada

The Nest Villa & Marina in the heart of Islamorada

An aerial view captures a row of white-roofed villas along a turquoise lagoon, surrounded by lush greenery. The serene waters extend towards the horizon, with a distant shoreline visible, creating a tranquil and spacious atmosphere.

4.84 out of 5 average rating, 81 reviews

Villa 5034 on Duck Key BOAT SLIP available

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.

4.53 out of 5 average rating, 15 reviews

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

A wooden table with round seating is positioned on a covered porch, framed by vibrant tropical landscaping. Lush palm trees and clear blue skies are visible, creating a serene outdoor space. The view extends to a community pool area in the background.

4.74 out of 5 average rating, 61 reviews

Villa 5086 on Duck Key BOAT SLIP available

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, 119 reviews

Waterfront villa for families * Family friendly*

New place to stay

Villa 5021 on Duck Key - Boat Slip Available

A spacious outdoor area is showcased, featuring a covered porch with a ceiling fan. A view of the calm blue water and landscaped greenery is highlighted, presenting a sense of tranquility. The distant horizon features low buildings and sailboats, enhancing the serene coastal atmosphere.

4.91 out of 5 average rating, 47 reviews

Villa 5028 on Duck Key BOAT SLIP available

New place to stay

Villa 5008 on Duck Key - Boat Slip Available

Luxury villa rentals

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, 22 reviews

Indigo Reef water view Villa- #1 Guest Favorite

Villa in Islamorada

5 out of 5 average rating, 7 reviews

Isla Guava: FREE Boat Dockage Sept-Oct Only!

New place to stay

Isla Sol ~ Waterfront Oasis ~ Pool ~ Dock ~ Kayaks

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, 59 reviews

New Paradise On Sombrero Beach

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.

4.88 out of 5 average rating, 16 reviews

"Casa Sea Keys" -Oceanfront 8 Guests, Private Dock

A serene scene features palm trees silhouetted against a vibrant sunset sky. Warm hues reflect on the water's surface, while string lights hang delicately, adding a soft glow to the beachfront area. A sandy space below invites relaxation and enjoyment of the coastal view.

4.86 out of 5 average rating, 44 reviews

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

Aerial view of the Indigo Reef gated community, showcasing rows of villas surrounded by lush greenery. Crystal-clear waters are visible, with docks leading to the ocean. The vibrant blue sky extends over the scene, reflecting the peaceful coastal environment.

5 out of 5 average rating, 13 reviews

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

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.

4.41 out of 5 average rating, 27 reviews

2BR water view with private pool, balcony & kayak

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, 12 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.

4.96 out of 5 average rating, 93 reviews

Waterfront Island Escape with Private Plunge Pool

4.73 out of 5 average rating, 11 reviews

Latitudes #34 Key Largo 4BR Villa | Pool + Resort

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, 3 reviews

Luxury Waterfront Villa, Marathon, Florida Keys

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 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, 11 reviews

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

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.