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2026-08-11
2026-08-12
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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 the 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 just steps from the Lower Matecumbe Key, 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 the Indian… More

From US$ 681 Book Now

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

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

Offering a wellness centre and an outdoor swimming pool for guests' leisure, Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! Islamorada villa is situated just 1 km from the… More

From US$ 1093 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 the Islamorada, located merely a 10-minute walk away. Providing guests with Wi-Fi and a private… More

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Executive Bay Islamorada By Sofla Vacations

87200 Overseas Highway, Islamorada, United States Show map

Situated within 5 minutes' walk of the Islamorada, the 8-room Executive Bay Islamorada By Sofla Vacations villa offers quick access to numerous city landmarks nearby. Providing guests with Wi-Fi and… More

From US$ 150 Book Now

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

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

Along with proximity to the Windley Key Fossil Reef Geological State Park, merely 500 metres away, At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa offers opportunities for… More

From US$ 467 Book Now

Pineapple Beach

130 Aregood Lane, Islamorada, United States Show map

During the stay at Pineapple Beach Islamorada villa, guests can indulge in cycling and fishing or visit the Rain Barrel Village, located 2.5 km away. Featuring a hot tub, this holiday home is 25… 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

Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa is nestled 9 minutes' walk from the Lobster Trap Art Gift Shop and Gallery and can accommodate up to 6 guests. More

From US$ 722 Book Now

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

The 3-bedroom Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa accommodates up to 7 guests and offers proximity to the Windley Key Fossil Reef Geological State Park, located just… 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 hosts up to 8 guests and provides proximity to the Windley Key Fossil Reef Geological… More

From US$ 723 Book Now

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

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

Along with proximity to the 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

Islamorada Modern Penthouse With Private Beach

80639 Old Highway, Islamorada, United States Show map

Located only a 7-minute walk from the Indian Key State Historic Site, the 3-bedroom Islamorada Modern Penthouse With Private Beach villa is suitable for 7 guests and provides a Jacuzzi for a truly… More

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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 the 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

During the stay at Bella Villa Islamorada, guests can indulge in bowling and billiards or visit the 45 - acre Founders Park, located 20 minutes' walk away. More

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Paradise Palms Islamorada

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

Paradise Palms Islamorada villa entices guests to enjoy snorkelling, canoeing, and ping-pong and offers proximity to the Windley Key Fossil Reef Geological State Park, located only 0.7 km away. More

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The Oasis

82703 Old Highway, Islamorada, United States Show map

The 3-bedroom The Oasis Villa Islamorada is situated approximately 2 km from the Michelle Nicole Lowe Art Gallery and boasts bicycles for active guests. This property is nestled in a beach area of… More

From US$ 1964 Book Now

Palms 407

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

During the stay at the 2-bedroom Palms 407 Villa Islamorada, guests can indulge in windsurfing, snorkelling, and bowling or visit the Michelle Nicole Lowe Art Gallery, located 3.2 km away. Featuring… More

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Beacon Reef 501

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

The 2-bedroom Beacon Reef 501 Villa Islamorada is nestled nearly 5 minutes' walk from Island Community Church and entices guests with a hot tub. Located within 2 km of the Lobster Trap Art Gift Shop… More

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

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

Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool Islamorada villa enjoys a convenient location 600 metres from the Windley Key Fossil Reef Geological State Park, and invites guests to spend time… More

From US$ 1403 Book Now

West Plaza Del Lago

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

Situated approximately 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. Suitable for up to 5 guests,… More

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Villa Riolo

130 Columbus Dr, Islamorada, United States Show map

The 2-bedroom Villa Riolo Islamorada hosts up to 6 guests and provides proximity to the Lower Matecumbe Key, situated merely a 5-minute stroll away. The Islamorada holiday home features opportunities… 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 the Lower Matecumbe Key, situated just a 5-minute walk away. This Islamorada villa… More

From US$ 450 Book Now

Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida

10610 San Remo Dr, Islamorada, United States Show map

Situated around 20 minutes' walk from the Rain Barrel Village, the 3-bedroom Waterside Cottage Accommodation With Private Swimming Pool In Islamorada, Florida invites guests to relax at a patio. More

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Waterfront Private Home, Pool, Dock, Sunsets, Tiki

81912 Overseas Highway, Islamorada, United States Show map

Waterfront Private Home, Pool, Dock, Sunsets, Tiki Islamorada with a prime location merely a 7-minute walk from the Hurricane Monument entices guests with a hot tub. Located just 1.8 km from the… 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. The 2-bedroom villa features… More

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Beacon Reef 306

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

Boasting a Jacuzzi, the 2-bedroom Beacon Reef 306 Villa Islamorada is located only 5 minutes' walk from the 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

Lyons Landing Villa Islamorada is located 7 km from the class museum "Florida Keys History and Discovery Center" and provides windsurfing, snorkelling, and diving for active guests. More

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Beacon Reef 222

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

The 2-bedroom Beacon Reef 222 Villa Islamorada entices guests to enjoy snorkelling and offers proximity to the History of Diving Museum, located just 300 metres away. The Islamorada villa can host up… 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 the Rain Barrel Sculpture Gallery, located 1.7 km away. The… More

From US$ 1011 Book Now

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 swimming 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 3.8 km from the Lobster Trap Art Gift Shop and Gallery and provides windsurfing, snorkelling, and bowling for active guests. Offering a Jacuzzi… 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 just 300 metres from the Lobster Trap Art Gift Shop and Gallery and can accommodate up to 12 guests. This 4-bedroom villa features opportunities… More

From US$ 823 Book Now

Beacon Reef 310

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

Offering a Jacuzzi for guests to unwind, the 2-bedroom Beacon Reef 310 Villa Islamorada is located within 5 minutes' walk of the History of Diving Museum. This Islamorada villa features opportunities… More

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La Dolce Vita Villa

116 Stromboli Dr, Islamorada, United States Show map

Situated nearly a 20-minute 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

Situated within 10 minutes' walk of the Keys History & Discovery Center, the 4-bedroom Hidden Gem Duplex In Heart Of Islamorada Sleeps 8 villa entices guests with fishing in the area. Providing… More

From US$ 1005 Book Now

Palms 313

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

During the stay at Palms 313 Villa Islamorada, guests can indulge in windsurfing, snorkelling, and bowling or visit the Lignumvitae Key Botanical State Park, located around 20 minutes' walk away. 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 the Lobster Trap Art Gift Shop and Gallery, located 3.4 km away. Offering a… More

From US$ 384 Book Now

Palms 309

79901 Overseas Hwy., Islamorada, United States Show map

Staying at the 2-bedroom Palms 309 Villa Islamorada, guests can easily reach the Indian Key State Historic Site, located approximately a 20-minute walk away. Suitable for up to 5 people, this… More

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Private Beach Private Overwater Dock Heated Pool Mahi Key

76321 Overseas Highway, Islamorada, United States Show map

At the 3-bedroom Private Beach Private Overwater Dock Heated Pool Mahi Key Islamorada villa, guests can enjoy snorkelling as well as a location in the immediate vicinity of the Lower Matecumbe Key. More

From US$ 1956 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 the Lobster Trap Art Gift Shop and Gallery, located 3.8 km away. The 1-bedroom holiday home… 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 the History of Diving Museum and provides a hot tub. With a maximum capacity of 3 guests, the Islamorada villa offers a… More

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Antigua Place

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

Offering a location around 4 km from the Craig Key, the 3-bedroom Antigua Place Islamorada villa gives access to various tourist spots in the area. Suitable for up to 6 guests, the property offers… 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 the 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 approximately 7… More

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Palms 301

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

The 2-bedroom Palms 301 Villa Islamorada is located around a 10-minute drive from the Hurricane Monument and provides a Jacuzzi. The Islamorada villa boasts an indoor water park and spa therapy… More

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Peninsula Villa Boat Dock Heated Pool Sunset Point

76414 Overseas Highway, Islamorada, United States Show map

Situated a stone's throw from the Lower Matecumbe Key, the 6-bedroom Peninsula Villa Boat Dock Heated Pool Sunset Point Islamorada is ideal for up to 12 guests. The holiday home features… More

From US$ 1939 Book Now

Little Bay Cottage

82246 Overseas Hwy, Islamorada, United States Show map

During the stay at Little Bay Cottage Islamorada, guests can indulge in windsurfing, snorkelling, and diving or visit the Michelle Nicole Lowe Art Gallery, located 15 minutes' walk away. More

From US$ 549 Book Now

Little Bay Compound

82246 Overseas Highway, Islamorada, United States Show map

The 6-bedroom Little Bay Compound Villa Islamorada entices guests to enjoy windsurfing, snorkelling, and diving and offers proximity to the Keys History & Discovery Center, located nearly a 10-minute… More

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Beacon Reef 406

83201 Old Hwy Unit #406, Islamorada, United States Show map

Beacon Reef 406 Villa Islamorada is situated just a 5-minute walk from the History of Diving Museum and offers a Jacuzzi, ensuring a more relaxing stay. This 2-bedroom villa features opportunities… More

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