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2026-11-10
2026-11-11
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Holiday Homes in Islamorada

Anglers Reef Paradise

110 Anglers Way 110, Islamorada, United States Show map

Anglers Reef Paradise Islamorada villa is located 5 minutes' walk from Windley Key Fossil Reef Geological State Park and offers guests to enjoy snorkelling, diving, and cycling. More

From US$ 382 Book Now

Key Lime Cottage In The Heart Of Islamorada

76777 Overseas Highway, Islamorada, United States Show map

Located only steps away from Lower Matecumbe Key Island, Key Lime Cottage In The Heart Of Islamorada is suitable for 5 guests and provides a heated pool to relax in. Located a 25-minute walk from… More

From US$ 326 Book Now

Margaritaville

87380 Overseas Highway, Islamorada, United States Show map

The 2-bedroom Margaritaville Islamorada villa accommodates up to 6 guests and offers proximity to Islamorada, located merely a 10-minute walk away. More

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At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom

84745 Old Hwy #6, Islamorada, United States Show map

Situated just 500 metres from Windley Key Fossil Reef Geological State Park, the 3-bedroom At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa is suitable for 6 guests and provides… More

From US$ 467 Book Now

Pineapple Beach - Luxury 5Br Oceanfront Estate With Heated Pool & Private Dock

130 Aregood Lane, Islamorada, United States Show map

During the stay at Pineapple Beach Islamorada villa, guests can indulge in cycling and fisheries or visit Rain Barrel Village, located 2.5 km away. Featuring a Jacuzzi, the 5-bedroom holiday home is… More

From US$ 2875 Book Now

Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

84 Johnston Ave Unit #7, Islamorada, United States Show map

Located 9 minutes' walk from Lobster Trap Art Gift Shop and Gallery, Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa is suitable for 6 guests and provides a… More

From US$ 722 Book Now

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

Situated only 0.7 km from Windley Key Fossil Reef Geological State Park, the 3-bedroom Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa is ideal for up to 7 guests. Providing guests… More

From US$ 624 Book Now

Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms

A1, 84745 Old Highway, Islamorada, United States Show map

The 3-bedroom Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms Islamorada villa accommodates up to 8 guests and offers proximity to Windley Key Fossil Reef Geological… More

From US$ 723 Book Now

Pristine Islamorada Pool Home With Ocean View And Dockage

148 Anglers Way, Islamorada, United States Show map

Located only 5 minutes' walk from Windley Key Fossil Reef Geological State Park, the 2-bedroom Pristine Islamorada Pool Home With Ocean View And Dockage boasts an outdoor swimming pool and can… More

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

84 Johnston Ave Unit #8, Islamorada, United States Show map

Along with proximity to Lobster Trap Art Gift Shop and Gallery, located only 9 minutes' stroll away, the 3-bedroom Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location… More

From US$ 1071 Book Now

Executive Bay Islamorada By Sofla Vacations

87200 Overseas Highway, Islamorada, United States Show map

Located just 0.7 km from Rain Barrel Village, the 2-room Executive Bay Islamorada By Sofla Vacations villa offers opportunities for snorkelling, diving, and fisheries in the area. This Islamorada… More

From US$ 150 Book Now

Waterfront 4Br,4Ba Home - Private Pool And Beach - Golf Cart - Dock - Sleeps 9

135 Gulfview Drive, Islamorada, United States Show map

Staying at Waterfront 4Br,4Ba Home - Private Pool And Beach - Golf Cart - Dock - Sleeps 9 Islamorada, guests can visit Craig Key Island, which is approximately a 10-minute ride away. More

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Islamorada Modern Penthouse With Private Beach

80639 Old Highway, Islamorada, United States Show map

Located just a 7-minute walk from Indian Key State Historic Site, the 3-bedroom Islamorada Modern Penthouse With Private Beach villa invites guests to enjoy a Jacuzzi. Located fairly close to FNX… More

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Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!

84 Johnston Ave Unit #9, Islamorada, United States Show map

Located 750 metres from Lobster Trap Art Gift Shop and Gallery, Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! Islamorada villa is suitable for 6 guests and provides an outdoor… More

From US$ 1093 Book Now

Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina

135 Anglers Way, Islamorada, United States Show map

Along with proximity to Windley Key Fossil Reef Geological State Park, a mere 0.6 km away, the 2-bedroom Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool… More

From US$ 394 Book Now

Bella

109 Valencia Drive, Islamorada, United States Show map

Featuring an outdoor swimming pool, Bella Villa Islamorada is located in a business part of Islamorada, 20 minutes' walk from the 45 - acre Founders Park. Providing guests with Wi-Fi and parking, the… More

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Is39Flr Tollgate Tides

205 Tollgate Blvd, Islamorada, United States Show map

Situated about 10 minutes by car from Lower Matecumbe Key Island, the 2-bedroom Is39Flr Tollgate Tides Villa Islamorada entices guests to explore various tourist attractions in the area. Guests can… More

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Paradise Palms Islamorada

84745 Old Highway Unit 9, Closest To The Ocean!, Islamorada, United States Show map

Located just 8 minutes on foot from Windley Key Fossil Reef Geological State Park, the 3-bedroom Paradise Palms Islamorada villa provides an outdoor swimming pool as well as canyoning, ping pong, and… More

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Palms 407

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

Nestled 3.2 km from Michelle Nicole Lowe Art Gallery, the 2-bedroom Palms 407 Villa Islamorada is boasting an aqua park and spa therapy for guests' enjoyment. This holiday home features opportunities… More

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Beacon Reef 501

83201 Old Highway #501, Islamorada, United States Show map

Located within 25 minutes' walk of Lobster Trap Art Gift Shop and Gallery, the 2-bedroom Beacon Reef 501 Villa Islamorada offers fitness classes, as well as a fitness room for active guests. Guests… More

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

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

Located 8 minutes' walk from Windley Key Fossil Reef Geological State Park, Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool Islamorada villa is suitable for 6 guests and provides a heated pool… More

From US$ 1403 Book Now

West Plaza Del Lago

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

Situated nearly 15 minutes' walk from Anne's Beach, the 2-bedroom West Plaza Del Lago Islamorada villa provides access to numerous tourist attractions in the area. The accommodation hosts up to 5… More

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Villa Riolo

130 Columbus Dr, Islamorada, United States Show map

Situated just moments from Lower Matecumbe Key Island, the 2-bedroom Villa Riolo Islamorada ensures a great leisure experience by offering snorkelling, diving, and bowling. The Islamorada holiday… More

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Waterfront Ocean Access Canal Kamp Key Homes

76412 Overseas Highway, Islamorada, United States Show map

The 3-bedroom Waterfront Ocean Access Canal Kamp Key Homes Islamorada hosts up to 6 guests and provides proximity to Lower Matecumbe Key Island, situated just a 5-minute walk away. This Islamorada… More

From US$ 450 Book Now

Is55Flr Captain'S Cove

227 El Capitan Dr, Islamorada, United States Show map

Situated nearly 15 minutes' walk from Anne's Beach, the 2-bedroom Is55Flr Captain'S Cove Islamorada villa provides fitness classes, as well as a fitness room for active guests. 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 around 20 minutes' walk from the 45-acre Founders Park and provides diving, canyoning, and… More

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Waterfront Private Home, Pool, Dock, Sunsets, Tiki

81912 Overseas Highway, Islamorada, United States Show map

Located 550 metres from Hurricane Monument, Waterfront Private Home, Pool, Dock, Sunsets, Tiki Islamorada is suitable for 7 guests and provides a Jacuzzi for a truly relaxing stay. This 4-bedroom… More

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Beacon Reef 307

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

Beacon Reef 307 Villa Islamorada provides an opportunity to stay a 5-minute walk from Island Community Church and offers a Jacuzzi, perfect for decompressing. Located 3 km from the shallow coral reef… More

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Is12Flr Paradise Beach

245 Sunset Dr, Islamorada, United States Show map

Staying at the 3-bedroom Is12Flr Paradise Beach Islamorada villa, guests can visit Anne's Beach, which is just a 5-minute walk away. Featuring fitness classes, as well as a fitness room for active… More

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Beacon Reef 306

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

Boasting a hot tub, the 2-bedroom Beacon Reef 306 Villa Islamorada is located around a 5-minute walk from History of Diving Museum and can accommodate 4 guests. This holiday home features… More

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Lyons Landing

105 Severino Drive, Islamorada, United States Show map

Featuring a heated pool, Lyons Landing Villa Islamorada is suitable for up to 10 people and is located about 7 km from the world-class museum "Florida Keys History and Discovery Center". Providing… More

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Beacon Reef 222

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

Situated approximately 5 minutes on foot from History of Diving Museum, the 2-bedroom Beacon Reef 222 Villa Islamorada ensures a great leisure experience by offering snorkelling. Hosting up to 4… More

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Fl Keys Venetian Shores Waterfront With Ocean Access, Pool

141 Stromboli Drive, Islamorada, United States Show map

During the stay at Fl Keys Venetian Shores Waterfront With Ocean Access, Pool Islamorada villa, guests can indulge in a Jacuzzi or visit Rain Barrel Sculpture Gallery, located 1.7 km away. The… More

From US$ 1011 Book Now

Bayside - Islamorada Waterfront, 360 Viewing Deck, Htd Swim Spa

422 Palm Dr, Islamorada, United States Show map

Bayside - Islamorada Waterfront, 360 Viewing Deck, Htd Swim Spa villa entices active guests with access to a fitness centre and is located around a 10-minute drive from Lower Matecumbe Key Island. More

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Casa Mar

115 Ponce De Leon Blvd, Islamorada, United States Show map

Located within 20 minutes' walk of Anne's Beach, the 3-bedroom Casa Mar Villa Islamorada boasts a heated pool with a hot tub. More

From US$ 657 Book Now

Palms 404

79901 Overseas Hwy Unit 404, Islamorada, United States Show map

The 2-bedroom Palms 404 Villa Islamorada is located approximately 10 minutes by car from Lobster Trap Art Gift Shop and Gallery and provides a Jacuzzi. This accommodation boasts an aqua park and spa… More

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Martin Family Fish Camp

106 Madeira Rd., Islamorada, United States Show map

Martin Family Fish Camp Villa Islamorada is nestled only a 5-minute walk from Lobster Trap Art Gift Shop and Gallery and can accommodate up to 12 guests. Located 2.2 km from Indian Key State Historic… More

From US$ 823 Book Now

Beacon Reef 310

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

Situated nearly 5 minutes' walk from Island Community Church, the 2-bedroom Beacon Reef 310 Villa Islamorada offers guests to take advantage of an aqua park and spa therapy. Featuring a Jacuzzi, this… More

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La Dolce Vita Villa

116 Stromboli Dr, Islamorada, United States Show map

Situated about 20 minutes' walk from the 45 - acre Founders Park, the 3-bedroom La Dolce Vita Villa Islamorada provides access to numerous tourist attractions in the area. With a maximum capacity of… More

From US$ 333 Book Now

Hidden Gem Duplex In Heart Of Islamorada Sleeps 8

82236 Overseas Highway, Islamorada, United States Show map

Along with proximity to Keys History & Discovery Center, merely a 10-minute walk away, the 4-bedroom Hidden Gem Duplex In Heart Of Islamorada Sleeps 8 villa offers opportunities for fisheries in the… More

From US$ 1005 Book Now

Palms 313

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

Nestled approximately a 20-minute walk from Lignumvitae Key Botanical State Park, the 2-bedroom Palms 313 Villa Islamorada is boasting an aqua park and spa therapy for guests' enjoyment. This holiday… More

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Sunshine Place

84371 Overseas Hwy, Islamorada, United States Show map

During the stay at Sunshine Place Islamorada villa, guests can indulge in windsurfing, snorkelling, and bowling or visit Lobster Trap Art Gift Shop and Gallery, located 3.4 km away. The 1-bedroom… More

From US$ 384 Book Now

Palms 309

79901 Overseas Hwy., Islamorada, United States Show map

The 2-bedroom Palms 309 Villa Islamorada, located nearly 20 minutes' walk from Indian Key State Historic Site, invites guests to relax in a Jacuzzi. Offering a heated pool, this accommodation invites… More

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Private Beach Private Overwater Dock Heated Pool Mahi Key

76321 Overseas Highway, Islamorada, United States Show map

Located just a few steps from Lower Matecumbe Key Island, the 3-bedroom Private Beach Private Overwater Dock Heated Pool Mahi Key Islamorada villa offers a swimming pool for guests to relax by. This… More

From US$ 2307 Book Now

Palms 417

79901 Overseas Highway #417, Islamorada, United States Show map

During the stay at Palms 417 Villa Islamorada, guests can indulge in a Jacuzzi and a sauna or visit Lobster Trap Art Gift Shop and Gallery, located 3.8 km away. The 1-bedroom holiday home features… More

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Palms 317

79901 Overseas Hwy Unit 317, Islamorada, United States Show map

The 1-bedroom Palms 317 Villa Islamorada is located within a 6-km distance of History of Diving Museum and provides a Jacuzzi. With a maximum capacity of 3 guests, the Islamorada villa offers parking. More

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Antigua Place

126 Ponce De Leon Blvd, Islamorada, United States Show map

Offering a location approximately 4 km from Craig Key Island, the 3-bedroom Antigua Place Islamorada villa gives access to various tourist spots in the area. The property hosts up to 6 guests and… More

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Sandglass 4

74980 Overseas Hwy 4, Islamorada, United States Show map

During the stay at Sandglass 4 Islamorada villa, guests can indulge in windsurfing, snorkelling, and diving or visit the 280 - acre island "Lignumvitae Key Botanical State Park", located 5 km away. More

From US$ 696 Book Now

Beacon Reef 503

83201 Old Highway #503, Islamorada, United States Show map

Situated nearly 5 minutes' walk from History of Diving Museum, the 2-bedroom Beacon Reef 503 Villa Islamorada is ideal for up to 4 guests. Offering a hot tub, the accommodation is within 7 km of… More

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Palms 301

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

Located around a 10-minute ride from Michelle Nicole Lowe Art Gallery, the 2-bedroom Palms 301 Villa Islamorada boasts an outdoor swimming pool with a Jacuzzi. Featuring ocean views, the Islamorada… More

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