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522 Villa rentals in Islamorada, FL
10 19 reviews
Islamorada, FL
08/07 – 08/23
$714/nighttotal: $11424 (16 )
Closest Oceanfront Home - 3 Stories, Views & Dock
3 4
house , Islamorada, Village of Islands
Paradise Palms, an oceanfront Islamorada villa in the Village of Islands, offers private dockage for boats up to 26 feet and is a five-minute walk from a Starbucks, near Robbie's Marina, Theater of the Sea, and Founders Park. This three-bedroom, three-bathroom vacation home sleeps eight, boasts a gourmet kitchen, 86-inch 4K TV, game room, community pool access, and expansive oceanfront balconies with views of Alligator Reef Lighthouse and the Islamorada Sandbar.
10 1 review
Islamorada, FL
06/27 – 07/04
$500/nighttotal: $3500 (7 )
149 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 2
house , Islamorada, Village of Islands
This 3-bedroom Islamorada, Village of Islands house is perfect for a family vacation. It has a spacious floor plan with 1600 square feet of living space and can accommodate up to 8 guests. The house is fully equipped with a kitchen, air conditioning, a swimming pool, a terrace, a garden, and parking. It also has internet access, making it easy to stay connected during your stay.
9.4 18 reviews
Islamorada, FL
09/08 – 10/06
$138/nighttotal: $3864 (28 )
Exec Bay W/heated Pool, Marina, Beach, Pets Ok, Tennis/pickleball
3 2
house , Islamorada, Village of Islands
This Islamorada townhouse rental, located at mile marker 87 in the Executive Bay Club, offers easy access to Founders Park and its beach, plus proximity to John Pennekamp Coral Reef State Park and Indian Key Historic State Park. This 1,370-square-foot, three-bedroom, two-bathroom vacation home sleeps six and features a fully equipped kitchen, in-unit laundry, a private terrace, access to a community pool, tennis/pickleball courts, and a private beach.
8.0 1 review
Islamorada, FL
10/09 – 10/12
$396/nighttotal: $1188 (3 )
Coral Penthouse Key Largo Ocean Pointe 4216
2 2
house , Tavernier
Coral Penthouse Key Largo Ocean Pointe 4216, located in Key Largo, offers stunning ocean views and is a short distance from Harry Harris Park Beach and John Pennekamp Coral Reef State Park. This 830-square-foot penthouse sleeps seven guests and boasts two bedrooms, two bathrooms, a private patio, swimming pool, Jacuzzi, full kitchen, and free Wi-Fi.
Islamorada, FL
01/01 – 05/31
$3074/nighttotal: $461100 (150 )
123 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 2
house , Islamorada, Village of Islands
House listing for up to 6 people. You will stay in Islamorada, Village of Islands. Services and facilities include a fridge, a freeze and a washing machine. Enjoy a swimming pool in this house in Islamorada, Village of Islands!
Islamorada, FL
09/08 – 10/06
$273/nighttotal: $7644 (28 )
Villa Riolo
2 2
house , Islamorada, Village of Islands
Villa Riolo, in Islamorada, Florida, offers a two-bedroom, two-bathroom house conveniently located 1.6 miles from Sea Oats Beach and within easy driving distance of Upper Matecumbe Key and Windley Key. This Islamorada vacation rental sleeps up to 11 guests and boasts a fully equipped kitchen, free Wi-Fi, on-site parking, a spa, and a fitness center, providing comfortable accommodations near Florida Keys attractions like John Pennekamp State Park.
Islamorada, FL
08/07 – 08/23
$490/nighttotal: $7840 (16 )
Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location
3 4
house , Islamorada, Village of Islands
Isla Key Lychee, a waterfront villa in Islamorada, is a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key, offering easy access to nearby attractions like Pigeon Key and John Pennekamp Coral Reef State Park. This 1680-square-foot, three-bedroom, three-bathroom house sleeps nine and features a fully equipped kitchen, swimming pool, fitness center, free Wi-Fi, and on-site parking.
Isla Key Lime: Waterfront Boutique Resort in Matecumbe, Islamorada, offers a three-bedroom villa within a 10-minute walk of the Islamorada Brewery & Distillery and Keys History & Discovery Center, and a 15-minute walk from the History of Diving Museum. This 1680-square-foot smoke-free property features a fully equipped kitchen, private balcony, heated pool, dock, and barbecue grills, accommodating up to six guests and offering free WiFi.
Islamorada, FL
09/08 – 10/06
$466/nighttotal: $13048 (28 )
Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
3 2
house , Islamorada, Village of Islands
Isla Mirabelle, a waterfront vacation home in Islamorada, offers private dock access and is a 12-minute walk from Upper Matecumbe Key, 2.7 miles from Windley Key, and 13 miles from Pigeon Key. This 1,680-square-foot house features three bedrooms, three bathrooms, sleeps nine guests, and includes a heated pool, fitness center, free Wi-Fi, and a fully equipped kitchen.
10 2 reviews
Islamorada, FL
08/07 – 08/23
$491/nighttotal: $7856 (16 )
Isla Kiwi: Waterfront Boutique Resort, Free Boat Dockage Sept-oct Only
3 4
house , Islamorada, Village of Islands
Isla Kiwi, a waterfront boutique resort in Islamorada's Matecumbe district, is within walking distance of the Islamorada Brewery & Distillery and Keys History & Discovery Center, and a short drive from the History of Diving Museum. This smoke-free, 1680-square-foot villa features three bedrooms, four bathrooms, accommodates six guests, and offers a private balcony, fully equipped kitchen, a swimming pool, and access to a garden with barbecue grills.
Islamorada, FL
08/07 – 08/23
$492/nighttotal: $7872 (16 )
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
3 4
house , Islamorada, Village of Islands
Isla Key Kiwi, a waterfront villa in Islamorada, offers stunning views and is a short walk from Upper Matecumbe Key, providing easy access to Windley Key, Pigeon Key, and John Pennekamp Coral Reef State Park. This 1680-square-foot vacation home features three bedrooms, three bathrooms, sleeps nine guests, and includes a private pool, fitness center, and fully equipped kitchen with a dishwasher; free Wi-Fi and parking are also provided.
Islamorada, FL
07/30 – 08/06
$292/nighttotal: $2044 (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.
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.
Isla Mirabelle, a three-bedroom waterfront villa in Islamorada's Matecumbe district, is a 10-minute walk from the Islamorada Brewery & Distillery and Keys History & Discovery Center, and within 15 minutes of the History of Diving Museum. This 1680-square-foot smoke-free property sleeps six, boasting a fully equipped kitchen, private balcony, heated pool, dock, and barbecue grills, all within walking distance of local attractions.
10 1 review
Islamorada, FL
08/03 – 08/05
$385/nighttotal: $770 (2 )
It's Island Time In The Keys Double King Ensuites 2 Balconies
2 5
house , Tavernier
This Key Largo vacation home is located a 15-minute walk from Harry Harris Park Beach, 2.8 miles from Pigeon Key, and within 11 miles of Upper Matecumbe Key and Windley Key Fossil Reef Geological State Park. This 830-square-foot property boasts two king ensuite bedrooms, two bathrooms, a private garden, swimming pool, Jacuzzi, and can comfortably accommodate eight guests, offering free Wi-Fi and a fully equipped kitchen.
Islamorada, FL
06/27 – 07/04
$3101/nighttotal: $21707 (7 )
Islamorada Beach - Beachfront, Fire Pit & Pool
6 2
house , Islamorada, Village of Islands
This 6-bedroom beachfront vacation home in Islamorada, Village of Islands, offers direct access to a private beach and is located 1.1 miles from Theater of the Sea and 1.6 miles from Windley Key. This spacious 3080 square foot residence accommodates up to 23 guests with a private outdoor pool, garden, terrace with sea views, a well-equipped kitchen, outdoor dining area, and a fire pit.
Islamorada, FL
07/30 – 08/06
$797/nighttotal: $5579 (7 )
Mirage - Islamorada Oceanfront Community, 3br, Near Sandbar, Pool
2 2
house , Islamorada, Village of Islands
This oceanfront villa in the Mirage community of Islamorada is located 2.9 miles from Upper Matecumbe Key and 10 miles from Pigeon Key, offering proximity to Windley Key Fossil Reef Geological State Park and Theater of the Sea. This 1680 sq ft villa accommodates up to 9 guests with 2 bedrooms and 3 bathrooms, featuring an oceanfront patio, balcony with sea views, a well-equipped kitchen, complimentary WiFi, private parking, an outdoor swimming pool, and a fitness room.
Best Islamorada, FL houses with a kitchen
9.3 3 reviews
Islamorada, FL
06/28 – 07/01
$416/nighttotal: $1248 (3 )
Salty Mermaid Ocean Pointe 4406
2 5
house , Tavernier
Salty Mermaid Ocean Pointe 4406, a Tavernier vacation home, is a short walk from Harry Harris Park Beach and minutes from Pigeon Key, Windley Key, and John Pennekamp Coral Reef State Park. This 860-square-foot rental boasts two bedrooms, two bathrooms, sleeps eight guests, and includes a private patio with ocean views, a fully equipped kitchen, swimming pool, Jacuzzi, and free Wi-Fi.
8.8 10 reviews
Islamorada, FL
08/03 – 08/05
$367/nighttotal: $734 (2 )
Ocean Pointe 2309
2 5
house , Tavernier
Ocean Pointe 2309, a Tavernier vacation home, is a 14-minute walk from Harry Harris Park Beach and 3 miles from Pigeon Key. This 910-square-foot property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private pool, bar, free Wi-Fi, and free parking.
Isla Guava: Waterfront Boutique Resort in Islamorada's Matecumbe district offers convenient access to the Islamorada Brewery & Distillery and Keys History & Discovery Center, both within a 10-minute walk, and the History of Diving Museum within 15 minutes. This 1680-square-foot, three-bedroom, four-bathroom villa sleeps six and boasts a fully equipped kitchen, private balcony, on-site garden with barbecue grills, a heated pool, dock, and free WiFi.
9.3 10 reviews
Islamorada, FL
10/09 – 10/12
$299/nighttotal: $897 (3 )
Modern And Coastal Ocean Pointe 2307
2 2
house , Tavernier
Ocean Pointe 2307 in Key Largo, a short 15-minute walk from Harry Harris Park Beach and near Pigeon Key (2.8 miles) and Windley Key (8.1 miles), offers this modern coastal-designed house with ocean views. This 900-square-foot vacation rental boasts two bedrooms, two bathrooms, accommodates eight guests, and includes a private patio, swimming pool, Jacuzzi, and fully equipped kitchen with a dishwasher, microwave, and refrigerator; free Wi-Fi and cable TV are also provided.
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?
This canal front vacation home is located on Lower Matecumbe Key in Islamorada, at Mile Marker 75, providing bayside access. This 2,770 sq ft villa accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, featuring a modern kitchen, air conditioning, a swimming pool, a tiki hut, and ample outdoor living space for family and friends.
Islamorada, FL
07/07 – 07/11
$889/nighttotal: $3556 (4 )
Oceanfront Cottage In Islamorada! Swimming Pool, Pets Allowed, Free Parking!
1 4
cottage , Islamorada, Village of Islands
This Islamorada pet-friendly cottage, located in the Matecumbe district, offers easy access to Bud n' Mary's Dive Center (a 14-minute walk) and Indian Key Historic State Park (a 6-minute walk). This one-bedroom, one-bathroom vacation home sleeps four and features a private balcony, shared pool access, kayaks, bicycles, free Wi-Fi, and a fully equipped kitchen; nearby attractions include Hurricane Monument and several state parks.
10 10 reviews
Islamorada, FL
08/07 – 08/23
$585/nighttotal: $9360 (16 )
Forever Views
3 4
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.
Islamorada, FL
09/08 – 10/06
$244/nighttotal: $6832 (28 )
Beacon Reef 307
2 2
house , Islamorada, Village of Islands
Beacon Reef 307, a beachfront Islamorada vacation home, is a short walk from the History of Diving Museum and less than 2 miles from Windley Key Fossil Reef Geological State Park and Upper Matecumbe Key. This two-bedroom, two-bathroom rental sleeps seven, boasting a fully equipped kitchen, private balcony with ocean views, Jacuzzi, fitness center, and free Wi-Fi; nearby activities include exploring the state park and museum.
Best Islamorada, FL villas and beach houses with jacuzzi
Islamorada, FL
07/07 – 07/11
$2650/nighttotal: $10600 (4 )
Oceanfront + Resort Perks | 4br Villa (Sleeps 8)
4 4
house , Islamorada, Village of Islands
This Islamorada vacation home, located in the Village of Islands, offers spectacular Atlantic Ocean views and proximity to local attractions. This 3,100-square-foot villa features four bedrooms, four bathrooms, and accommodates eight guests, boasting a private pool, jacuzzi, fitness center, full kitchen, and two-car garage.
Islamorada, FL
07/07 – 07/11
$324/nighttotal: $1296 (4 )
Marina And Ocean View 2 Bed 2 Bath End Unit 4201
2 4
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.
This waterfront estate in Tavernier features direct ocean views and is located near Old Road Gallery, History of Diving Museum, Hurricane Monument, and Indian Key Historic State Park. This 7390 square foot mansion accommodates up to 26 guests with 9 bedrooms and 10 bathrooms, offering a resort-style pool, hot tub, two secluded beaches, and a private deep water boat basin with over 100 feet of dockage and a boat ramp.
9.8 6 reviews
Islamorada, FL
10/09 – 10/12
$301/nighttotal: $903 (3 )
Marina To Ocean View Key Largo Ocean Pointe 5308
1 2
house , Tavernier
Ocean Pointe 5308 in Key Largo, a 15-minute walk from Harry Harris Park Beach, offers easy access to Pigeon Key (2.8 miles), Upper Matecumbe Key (11 miles), and Windley Key Fossil Reef Geological State Park (8.9 miles). This 830-square-foot Key Largo vacation home features two bedrooms, two bathrooms, accommodates six guests, and includes a pool, Jacuzzi, and fully equipped kitchen with a dishwasher; free Wi-Fi and cable TV are also provided.
