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2026-10-30
2026-10-31
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Extended Stay in Islamorada

Beacon Reef 307

83201 Old Hwy #307, Islamorada, United States Show map

Located around a 5-minute walk from History of Diving Museum, the 2-bedroom Beacon Reef 307 Villa Islamorada is suitable for 4 guests and provides a Jacuzzi for a truly relaxing stay. This holiday… More

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Mirage - Islamorada Oceanfront Community, 3Br, Near Sandbar, Pool

84745 Old Hwy #13, Islamorada, United States Show map

Situated 600 metres from Windley Key Fossil Reef Geological State Park, Mirage - Islamorada Oceanfront Community, 3Br, Near Sandbar, Pool villa offers guests to relax by an outdoor swimming pool. The… More

From US$ 727 Book Now

Is39Flr Tollgate Tides

205 Tollgate Blvd, Islamorada, United States Show map

The 2-bedroom Is39Flr Tollgate Tides Villa Islamorada entices active guests with access to a fitness suite and is located around a 5-minute stroll from Anne's Beach. More

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Private Beach Heated Pool Volleyball Court Orchid Beach Key

77145 Overseas Hwy, Islamorada, United States Show map

Located nearly 20 minutes' walk from Indian Key Historic State Park, the 4-bedroom Private Beach Heated Pool Volleyball Court Orchid Beach Key Islamorada villa boasts an outdoor swimming pool with a… More

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Hidden Gem Duplex In Heart Of Islamorada Sleeps 8

82236 Overseas Highway, Islamorada, United States Show map

Hidden Gem Duplex In Heart Of Islamorada Sleeps 8 villa is located 25 minutes' walk from Lignumvitae Key Botanical State Park and invites guests to join fisheries. More

From US$ 1005 Book Now

Bella

109 Valencia Drive, Islamorada, United States Show map

Featuring an outdoor swimming pool, Bella Villa Islamorada is suitable for up to 9 people and is located around 15 minutes' walk from Rain Barrel Village. Located in proximity to Windley Key Fossil… More

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Luxury 3Br Coastal Escape In Islamorada

80639 Old Highway, Apt 309, Islamorada, United States Show map

The 2275 m² Luxury 3Br Coastal Escape In Islamorada apartment is 17 minutes' walk from Gallery Morada and provides spa facilities such as a hot tub and a sauna. Situated within a few blocks of Indian… More

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Waterfront Ocean Access Canal Kamp Key Homes

76412 Overseas Highway, Islamorada, United States Show map

Waterfront Ocean Access Canal Kamp Key Homes Islamorada is nestled in close proximity to Lower Matecumbe Key Island and can accommodate up to 6 guests. Located 10 minutes' drive from Anne's Beach… More

From US$ 450 Book Now

Is17Flr - Executive Bay Club Condo

87200 Overseas Highway Unit M-1, Islamorada, United States Show map

Providing guests with an aqua park and a dining table to ensure a memorable stay, the 2-bedroom Is17Flr - Executive Bay Club Condo Islamorada villa is only 10 minutes' walk from Rain Barrel Sculpture… More

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Palms 407

79901 Overseas Hwy Unit 407, Islamorada, United States Show map

Featuring an outdoor swimming pool, the 2-bedroom Palms 407 Villa Islamorada is suitable for up to 4 people and is located within 6 km of History of Diving Museum. This Islamorada holiday home boasts… More

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Little Bay Compound

82246 Overseas Highway, Islamorada, United States Show map

Providing guests with an aqua park and spa therapy to ensure a memorable stay, the 6-bedroom Little Bay Compound Villa Islamorada is around a 10-minute walk from Keys History & Discovery Center. More

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West Plaza Del Lago

63 W Plaza Del Lago, Islamorada, United States Show map

During the stay at West Plaza Del Lago Islamorada villa, guests can indulge in windsurfing, snorkelling, and diving or visit Lower Matecumbe Key Island, located a 25-minute walk away. With a maximum… More

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Off The Charts-Waterfront Tiki Bar & Private Dock

110 Madeira Road, Islamorada, United States Show map

Staying at the 3-bedroom Off The Charts-Waterfront Tiki Bar & Private Dock Villa Islamorada, guests can visit Hurricane Monument, which is a mere 14 minutes' stroll away. The Islamorada villa is… More

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Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location

84 Johnston Ave Unit #5, Islamorada, United States Show map

Located merely 1.2 km from Upper Matecumbe Key Island, the 3-bedroom Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa has an outdoor swimming pool and is… More

From US$ 605 Book Now

Beacon Reef 222

83201 Old Highway Unit 222, Islamorada, United States Show map

Located just 5 minutes' walk from History of Diving Museum, the 2-bedroom Beacon Reef 222 Villa Islamorada features an outdoor swimming pool and can accommodate up to 4 guests. This 2-bathroom villa… More

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Little Bay Lower

82246 Overseas Hwy, Islamorada, United States Show map

To enjoy your vacation in Islamorada, stay at the 2-bedroom Little Bay Lower Islamorada apartment, which is 2.2 km from Lignumvitae Key Botanical State Park and just 12 minutes' walk from Lobster… More

From US$ 621 Book Now

Island Time - Oceanview Balconies- Dock- Htd Pool

84745 Old Hwy #12, Islamorada, United States Show map

Situated only 8 minutes on foot from Windley Key Fossil Reef Geological State Park, the 3-bedroom Island Time - Oceanview Balconies- Dock- Htd Pool Villa Islamorada ensures a great leisure experience… More

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Ocean View Duplex Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key One

101 Gulfview Drive Apt 314 Building D, Islamorada, United States Show map

The spacious 325 m² Ocean View Duplex Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key One Islamorada is located in Islamorada, around a 25-minute stroll from Lower Matecumbe Key… More

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Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location

84 Johnston Ave Unit #6, Islamorada, United States Show map

Located just a 9-minute walk from Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa features an… More

From US$ 872 Book Now

Beacon Reef #204

83201 Old Highway, Islamorada, United States Show map

The 118 m² Beacon Reef #204 Apartment Islamorada offers setting in a beach area of Islamorada, about a 5-minute walk from History of Diving Museum. Offering a terrace and barbecue, this 2-bedroom… More

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Tea Table Key

79775 Overseas Highway, Islamorada, United States Show map

The 6-bedroom Tea Table Key Villa Islamorada is located around 10 minutes' drive from Lignumvitae Key Botanical State Park and provides a Jacuzzi. With a maximum capacity of 12 guests, the property… More

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Is12Flr Paradise Beach

245 Sunset Dr, Islamorada, United States Show map

Situated 3 km from Lower Matecumbe Key Island, Is12Flr Paradise Beach Islamorada villa entices guests to explore various tourist attractions in the area. The 3-bedroom holiday home hosts up to 8… More

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Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida

10610 San Remo Dr, Islamorada, United States Show map

The 3-bedroom Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida is located about a 20-minute stroll from the 45-acre Founders Park and allows guests to enjoy diving… More

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Beacon Reef 306

83201 Old Hwy Unit 306, Islamorada, United States Show map

The 2-bedroom Beacon Reef 306 Villa Islamorada is located within 5 minutes' walk of Island Community Church and offers a hot tub for guests' relaxation. This Islamorada holiday home can accommodate… More

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Waterfront Private Home, Pool, Dock, Sunsets, Tiki

81912 Overseas Highway, Islamorada, United States Show map

Featuring a heated pool, the 4-bedroom Waterfront Private Home, Pool, Dock, Sunsets, Tiki Islamorada is located about 5 minutes' walk from Michelle Nicole Lowe Art Gallery and is suitable for up to 7… More

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Palms 301

79901 Overseas Hwy Unit 301, Islamorada, United States Show map

During the stay at the 2-bedroom Palms 301 Villa Islamorada, guests can indulge in windsurfing, snorkelling, and bowling or visit Lignumvitae Key Botanical State Park, located about 20 minutes' walk… More

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Palms 313

79901 Overseas Hwy Unit 313, Islamorada, United States Show map

The 2-bedroom Palms 313 Villa Islamorada can host up to 5 guests, boasting a beachfront location within a 6-km distance of iconic cultural attractions such as History of Diving Museum. Featuring a… More

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Beacon Reef 310

83201 Old Highway #310, Islamorada, United States Show map

Offering guests to unwind in a Jacuzzi, Beacon Reef 310 Villa Islamorada is located 25 minutes' walk from Upper Matecumbe Key Island. Guests can enjoy windsurfing, snorkelling, and canyoning at the 2… More

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Ocean View Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key Two

101 Gulfview Drive Apt #D316 Building D, Islamorada, United States Show map

To enjoy your vacation in Islamorada, stay at the spacious 188 m² Ocean View Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key Two Islamorada apartment, which is only 1.2 km from Anne's… More

From US$ 1446 Book Now

Ocean View Two Duplex Penthouses Retreat Amenities: Tennis Court Heated Pool Vista Key

101 Gulfview Drive Apt 314-316, Islamorada, United States Show map

The spacious Ocean View Two Duplex Penthouses Retreat Amenities: Tennis Court Heated Pool Vista Key Islamorada is located 3.6 km from Craig Key Island and a 15-minute stroll from Anne's Beach. Wi-Fi… More

From US$ 1899 Book Now

Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool

84745 Old Hwy #14, Islamorada, United States Show map

Situated only 8 minutes' walk from Windley Key Fossil Reef Geological State Park, the 3-bedroom Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool Islamorada villa entices guests with snorkelling,… More

From US$ 1403 Book Now