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522 Villa rentals in Islamorada, FL
9.7 7 reviews
Islamorada, FL
10/17 – 10/26
$571/nighttotal: $5139 (9 )
Isla Mirabelle: Free Boat Dockage Sep-oct Only!
1 6
house , Islamorada, Village of Islands
This upscale villa is located in the Art District of Islamorada, just a short walk from shops, restaurants, and parks. The villa is part of a luxurious community of nine villas, featuring a private heated pool and BBQ area. This 3-bedroom, 3-bathroom villa comfortably accommodates up to 6 guests. It offers breathtaking sunset views, direct access to a private boat dock on the bay, and a full-service Guest Experience Team for 24/7 support.
Islamorada, FL
07/19 – 07/26
$397/nighttotal: $2779 (7 )
House ∙ 3 Bedrooms ∙ 10 Guests
3 9
house , Islamorada, Village of Islands
This Keys-style waterfront home in Delray Beach offers direct ocean-access canal frontage, ideal for boating and fishing, with a private dock for immediate waterway exploration. This 3-bedroom, 3-bathroom villa accommodates up to 10 guests and features a heated pool, outdoor bar, shaded patio, high-speed Wi-Fi, and provided beach gear for a comfortable stay.
Islamorada, FL
09/08 – 10/06
$179/nighttotal: $5012 (28 )
Palms 301
2 2
house , Islamorada, Village of Islands
Palms 301, a two-bedroom Islamorada vacation home, is conveniently located 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key, offering easy access to nearby attractions like Pigeon Key (15 miles) and John Pennekamp Coral Reef State Park (23 miles). This Islamorada rental boasts a fully equipped kitchen, a private pool, jacuzzi, spa, and fitness center, comfortably accommodating up to 11 guests with free Wi-Fi and on-site parking.
9.8 22 reviews
Islamorada, FL
10/09 – 10/12
$285/nighttotal: $855 (3 )
Starfish Seas Key Largo Ocean Pointe 1302
2 2
house , Tavernier
Starfish Seas Key Largo Ocean Pointe 1302, located in Key Largo, offers ocean views and is a short walk from Harry Harris Park Beach, with easy access to Pigeon Key and other attractions like John Pennekamp State Park. This 830-square-foot Key Largo vacation home features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, Jacuzzi, and free Wi-Fi.
Islamorada, FL
07/01 – 07/08
$1185/nighttotal: $8295 (7 )
Heart Of Morada
3 2
house , Islamorada, Village of Islands
This 3-bedroom, 4-bathroom vacation home in Islamorada, Village of Islands, is a 2-minute walk from Upper Matecumbe Key and near attractions like Theater of the Sea. This 1850 square foot rental accommodates up to 10 guests and features a private pool, balcony with outdoor furniture, fireplace, barbecue, electric vehicle charging station, and access to water sports.
9.7 15 reviews
Islamorada, FL
10/09 – 10/12
$428/nighttotal: $1284 (3 )
The Nest Villa & Marina In The Heart Of Islamorada
1 2
house , Islamorada, Village of Islands
This Islamorada villa offers a central location, a short walk from shops, restaurants, and a brewery, providing easy access to world-class fishing and diving. The two-bedroom, two-bathroom house sleeps four, features a private rooftop terrace with Florida Bay views, a private jetty for swimming and snorkeling, and two parking spaces, plus a protected marina with boat launch (max boat 26ft, launch up to 18ft).
9.7 11 reviews
Islamorada, FL
10/09 – 10/12
$272/nighttotal: $816 (3 )
Reel Key Largo Escape Ocean Pointe 5209
2 2
house , Tavernier
Ocean Pointe 5209 in Key Largo, a 15-minute walk from Harry Harris Park Beach and near Pigeon Key, Windley Key, and John Pennekamp State Park, offers this two-bedroom, two-bathroom vacation home. This 830-square-foot property features a private patio with ocean views, a swimming pool, Jacuzzi, and in-house amenities including Wi-Fi, cable TV, and a fully equipped kitchen; it comfortably sleeps six guests.
Islamorada, FL
01/01 – 05/31
$679/nighttotal: $101850 (150 )
316 M² House ∙ 4 Bedrooms ∙ 11 Guests
4 2
house , Islamorada, Village of Islands
This 3400 square foot house in Islamorada, Village of Islands, located in Plantation Key at Mile Marker 90, offers direct waterfront access with a 65-foot dock and is 700 feet from Tavernier Creek, providing easy access to the Atlantic Ocean and Florida Bay. This family-friendly vacation rental accommodates up to 11 guests with 4 bedrooms and 3 bathrooms, featuring a private heated pool, outdoor cooking amenities like a Blackstone griddle and Solo Stove fire pit, dual living areas, a game room, and a screened-in porch, with optional concierge services available.
10 7 reviews
Islamorada, FL
07/30 – 08/06
$650/nighttotal: $4550 (7 )
Isla Mamey: Free Boat Dockage Sept-oct Only!
1 2
house , Islamorada, Village of Islands
Isla Mamey Villa #5, located in Islamorada's Art District, is a short walk from shops, restaurants, and parks, and minutes from attractions like Robbie's Marina and the Theater of the Sea. This three-bedroom, three-bathroom upscale villa offers a private pool, bayside boat dock, and sleeps six guests, boasting a modern, fully furnished interior with a sleek kitchen and private deck with partial water views.
Islamorada, FL
10/17 – 10/26
$510/nighttotal: $4590 (9 )
Waterfront Ocean Access Canal Kamp Key Homes
3 6
house , Islamorada, Village of Islands
This waterfront ocean access canal home in Islamorada offers direct canal access and is located 1.4 miles from Sea Oats Beach and 5.5 miles from Upper Matecumbe Key. This 3-bedroom, 3-bathroom villa accommodates up to 10 guests and features air conditioning, a balcony, a full kitchen with a dishwasher and oven, and a washing machine.
Islamorada, FL
07/02 – 07/05
$511/nighttotal: $1533 (3 )
Marina And Ocean View 2 Bed 2 Bath End Unit 4201
2 5
house , Tavernier
This Tavernier house rental boasts stunning sea views and offers a private patio, refreshing pool, and free Wi-Fi. The 910-square-foot home includes two bedrooms, two bathrooms, and accommodates up to nine guests, featuring a fully equipped kitchen with modern appliances and in-house laundry.
Islamorada, FL
07/01 – 07/08
$2728/nighttotal: $19096 (7 )
Private Beach Private Overwater Dock Heated Pool Mahi Key
3 2
house , Islamorada, Village of Islands
This Islamorada vacation home is located near Sea Oats Beach (1.4 miles), Upper Matecumbe Key (5.7 miles), and Theater of the Sea (8.3 miles), offering convenient access to local attractions. This 1,320-square-foot house features three bedrooms, three bathrooms, and accommodates up to ten guests, boasting a private overwater dock, heated pool, and balcony with ocean views.
Find the Best Holiday Houses with Swimming Pool in Islamorada, FL
A vacation home with a pool near the water in Islamorada, FL is the perfect base to complement your adventures.
Islamorada, FL
09/08 – 10/06
$2157/nighttotal: $60396 (28 )
Islamorada Retreat - Waterfront, Pool & Boat Dock
7 2
house , Islamorada, Village of Islands
This Islamorada vacation home is located directly on the waterfront with a private pool and boat dock, situated an 8-minute walk from Upper Matecumbe Key and 0.9 miles from the History of Diving Museum. This spacious 3150 sq ft air-conditioned house sleeps 29 guests with 7 bedrooms and 5 bathrooms, featuring a terrace with sea views, a well-equipped kitchen with a dishwasher and microwave, complimentary WiFi, and free private parking.
Islamorada, FL
07/19 – 07/26
$1095/nighttotal: $7665 (7 )
Tavernier Ocean Vista
5 9
house , Tavernier
Tavernier Ocean Vista is a five-bedroom, four-bathroom house in Tavernier, Florida, located 3.8 miles from Pigeon Key and 6.7 miles from Windley Key. This family-friendly vacation home sleeps 27 guests and boasts a private pool, free Wi-Fi, free parking, a fully equipped kitchen with a dishwasher, and free bikes for exploring the Tavernier area; it also includes on-site amenities like a mini-market and outdoor play equipment.
9.7 9 reviews
Islamorada, FL
10/09 – 10/12
$324/nighttotal: $972 (3 )
Ocean View Treehouse Double King Suite 3403
2 2
house , Tavernier
Ocean View Treehouse Double King Suite 3403 in Tavernier offers ocean views and is a short walk from Harry Harris Park Beach, 3.1 miles from Pigeon Key, and 8.3 miles from Windley Key. This 820-square-foot vacation rental boasts two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus a private patio, swimming pool, and garden.
10 10 reviews
Islamorada, FL
10/17 – 10/26
$596/nighttotal: $5364 (9 )
Forever Views
3 6
house , Islamorada, Village of Islands
This Islamorada vacation rental is located in the gated community of Bay Harbour at mile marker 77.5, just a short walk from a beach ideal for various water activities and a mile away from Anne's beach. The house has earned excellent ratings for its location, cleanliness, and overall user experience. The three-bedroom house comfortably accommodates up to six guests. The property features a gourmet kitchen, a private dock with a lift, a swimming pool, a spa, and a fitness center, making it perfect for a relaxing and enjoyable vacation.
Best Islamorada, FL houses with a kitchen
8.8 12 reviews
Islamorada, FL
10/09 – 10/12
$298/nighttotal: $894 (3 )
Lazy Daze Double King Suite Ocean Pointe 2310
2 2
house , Tavernier
Lazy Daze Double King Suite Ocean Pointe 2310, located in Key Largo, offers easy access to Harry Harris Park Beach, a 15-minute walk away. This 830-square-foot Key Largo vacation rental boasts two bedrooms with king-size beds, two bathrooms, a fully equipped kitchen, in-unit laundry, a private patio with ocean views, a swimming pool, and jacuzzi, accommodating up to six guests.
Islamorada, FL
07/01 – 07/08
$1789/nighttotal: $12523 (7 )
The Oasis
3 2
house , Islamorada, Village of Islands
This Islamorada vacation rental offers direct beachfront access with sea views from its terrace and lake views from its balcony, located a 0.5 mile walk from the History of Diving Museum and an 18-minute walk from Upper Matecumbe Key. This 2000 square foot, 3-bedroom, 3-bathroom house accommodates up to 14 guests and features a swimming pool, private beach area, complimentary bicycles, and is near water sports activities, Theater of the Sea (1.9 miles), and Windley Key (2.5 miles).
8.0 1 review
Islamorada, FL
07/01 – 07/08
$671/nighttotal: $4697 (7 )
At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom
1 2
house , Islamorada, Village of Islands
This Islamorada vacation home boasts an oceanfront location, a 10-minute walk from Windley Key and a short drive from Upper Matecumbe Key, Pigeon Key, and John Pennekamp Coral Reef State Park. This 1,750-square-foot property sleeps 12 guests and features a heated pool, spa, game room, free Wi-Fi, and a fully equipped kitchen with a dishwasher; on-site parking is also available.
Islamorada, FL
09/08 – 10/06
$235/nighttotal: $6580 (28 )
Beacon Reef 406
2 2
house , Islamorada, Village of Islands
Beacon Reef 406, a beachfront Islamorada vacation home, is a short walk from the History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park. This two-bedroom, two-bathroom rental sleeps seven guests and boasts a fully equipped kitchen, Jacuzzi, fitness center, spa, and free Wi-Fi, providing a luxurious and convenient stay.
Frequently Asked Questions about villa rentals in Islamorada, FL
What are the must-see attractions in and around Islamorada, FL?
Islamorada is known for its beautiful beaches and watersports, but you should also check out the Theater of the Sea, a marine park with dolphin and sea lion shows. If you're looking for a unique experience, head to the History of Islamorada Museum, which tells the story of the area's fishing and maritime heritage. And don't forget to take a drive down the Overseas Highway, a scenic route that connects the Florida Keys.
What are the best villa rentals in Islamorada, FL?
What types of wildlife can travelers expect to see in the area of Islamorada, FL?
You'll see lots of birds, including pelicans, herons, and osprey. The waters around Islamorada are home to a variety of marine life, such as dolphins, manatees, and sea turtles. You might even spot a shark or a ray if you're lucky.
What are the best villa rentals with a pool in Islamorada, FL?
The best time to visit Islamorada is during the shoulder seasons, from April to May and September to October. The weather is still warm, but the crowds are smaller and the prices are lower. You can also enjoy the best fishing during these months.
What are the best villa rentals with a jacuzzi in Islamorada, FL?
What are the top hiking trails near Islamorada, FL?
There aren't many hiking trails in Islamorada, as the area is mostly flat and coastal. However, you can enjoy a scenic walk along the Overseas Highway or take a kayak tour through the mangroves.
What are the best villa rentals for families and kids in Islamorada, FL?
What are the advantages of renting a house or a villa in Islamorada, FL
Renting a house or a villa in Islamorada gives you more space and privacy than a hotel room. You'll also have access to a kitchen, so you can save money by cooking some of your meals. And many rentals have a private pool or hot tub, which is a great way to relax and enjoy the Florida weather.
What are the best pet friendly villa rentals in Islamorada, FL?
Are there popular destinations near Islamorada, FL?
Yes, there are several popular destinations near Islamorada. You can easily drive to Key Largo, which is known for its diving and snorkeling. You can also visit the John Pennekamp Coral Reef State Park, which is home to a variety of marine life.
What are the best villa rentals with parking in Islamorada, FL?
Angler's Reef Resort is located in Islamorada, a short distance from Anne's Beach and within a 10-mile radius of Upper Matecumbe Key and Windley Key. The resort has received excellent ratings for location, cleanliness, and overall user experience. The resort offers a variety of accommodations, including rooms with private bathrooms and some with kitchens. Amenities include a private beach, a tranquil garden, an outdoor pool, BBQ facilities, free parking, and WiFi. Guests can also enjoy activities like cycling and exploring the surrounding area.
Islamorada, FL
09/08 – 10/06
$254/nighttotal: $7112 (28 )
Beacon Reef 222
2 2
house , Islamorada, Village of Islands
Beacon Reef 222, a two-bedroom Islamorada vacation home, is conveniently located near Upper Matecumbe Key and Windley Key, offering easy access to snorkeling and diving, with Pigeon Key 12 miles and John Pennekamp State Park 20 miles away. This 1,280-square-foot rental boasts two bathrooms, sleeps seven guests, and includes a private terrace with sea views, a swimming pool, fitness center, fully equipped kitchen, and free Wi-Fi.
Isla Lychee: Little Basin Villas, a waterfront boutique resort in Matecumbe, Islamorada, offers easy walking access to the Islamorada Brewery & Distillery and Keys History & Discovery Center, with the History of Diving Museum and Matecumbe United Methodist Church within a 15-minute drive. This smoke-free, 3-bedroom villa boasts 1680 square feet of space, accommodating up to 6 guests and featuring a fully equipped kitchen, private balcony, free Wi-Fi, and access to barbecue grills; a swimming pool is also available on the property.
Islamorada, FL
01/01 – 05/31
$2310/nighttotal: $346500 (150 )
Spectacular 4 Bedroom 4 1/2 Bath Villa On Tavernier Creek In Florida Keys.
4 2
house , Islamorada, Village of Islands
This villa in Tavernier offers direct access to Tavernier Creek, with immediate ocean and bay access, and is less than seven miles from Islamorada's dining and shopping. This four-bedroom, four-bathroom villa accommodates up to eight guests and features a private balcony, a summer kitchen with a professional gas grill, a swimming pool, a jacuzzi, and a stand-by generator.
Best Islamorada, FL villas and beach houses with jacuzzi
Islamorada, FL
07/01 – 07/08
$319/nighttotal: $2233 (7 )
Sunrise Penthouse 3316 Ocean Pointe 1br 2ba
1 2
house , Tavernier
This Tavernier vacation home offers a 13-minute walk to Harry Harris Park Beach, is 3.1 miles from Pigeon Key, and 9 miles from the Theater of the Sea. This 910 square foot house features 1 bedroom, 2 bathrooms, and accommodates up to 7 guests with air conditioning, a kitchen equipped with a fridge, microwave, and dishwasher, a Jacuzzi, garden, parking, and a private patio.
Islamorada, FL
09/08 – 10/06
$230/nighttotal: $6440 (28 )
Beacon Reef 501
2 2
house , Islamorada, Village of Islands
Beacon Reef 501 is a beachfront villa in Islamorada, Village of Islands, located 1.3 miles from Theater of the Sea and 1.5 miles from Upper Matecumbe Key. This 2-bedroom, 2-bathroom residence accommodates up to 7 guests and features a fully equipped kitchen, air conditioning, a jacuzzi, a terrace, a garden, a spa, a fitness center, and direct beach access with sea views.
9.5 6 reviews
Islamorada, FL
07/18 – 07/22
$383/nighttotal: $1532 (4 )
Ocean View Overlooking Marina Ocean Pointe 5305
2 4
house , Tavernier
Ocean Pointe 5305, a Key Largo vacation home near the marina, is a 12-minute walk from Harry Harris Park Beach and within 12 miles of Upper Matecumbe Key and 9 miles of Windley Key Fossil Reef Geological State Park. This 830-square-foot rental boasts two bedrooms, two bathrooms, sleeps seven, and features a private patio, swimming pool, Jacuzzi, and fully equipped kitchen with a dishwasher, microwave, and fridge; free Wi-Fi and cable TV are also included.
9.6 6 reviews
Islamorada, FL
07/30 – 08/06
$329/nighttotal: $2303 (7 )
Key Largo Baha Penthouse Ocean Pointe 1416
1 2
house , Tavernier
Key Largo Baha Penthouse Ocean Pointe 1416, a two-bedroom condo in Key Largo, offers stunning ocean views and is a short walk from Harry Harris Park Beach, with easy access to Pigeon Key, Windley Key, and John Pennekamp State Park. This 830-square-foot penthouse boasts two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, private patio, swimming pool, jacuzzi, and free Wi-Fi.
