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2026-10-31
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Holiday Homes in Islamorada

Anglers Reef Paradise

110 Anglers Way 110, Islamorada, United States Show map

Situated approximately a 5-minute walk from Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise Islamorada villa entices guests with snorkelling, diving, and cycling in the area. More

From US$ 382 Book Now

Key Lime Cottage In The Heart Of Islamorada

76777 Overseas Highway, Islamorada, United States Show map

Located just near Lower Matecumbe Key Island, 2-bedroom Key Lime Cottage In The Heart Of Islamorada boasts a heated pool and can accommodate up to 5. Providing guests with Wi-Fi and parking, this… More

From US$ 326 Book Now

Margaritaville

87380 Overseas Highway, Islamorada, United States Show map

Up to 6 guests can stay at Margaritaville Islamorada villa and enjoy Cowpens Anchorage, located a 6-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

Located 500 metres from Windley Key Fossil Reef Geological State Park, At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa is suitable for 6 guests and provides a year-round… More

From US$ 467 Book Now

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

Located 8 minutes' stroll from Windley Key Fossil Reef Geological State Park, Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa is suitable for 7 guests and provides a heated pool to… More

From US$ 624 Book Now

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

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

Located nearly a 15-minute walk from Hurricane Monument, the 3-bedroom Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa gives access to various tourist… More

From US$ 1071 Book Now

Executive Bay Islamorada By Sofla Vacations

87200 Overseas Highway, Islamorada, United States Show map

Featuring an outdoor swimming pool as well as views of the sea, Executive Bay Islamorada By Sofla Vacations villa offers a prime location a mere 10 minutes' walk from Rain Barrel Sculpture Gallery. More

From US$ 150 Book Now

Pristine Islamorada Pool Home With Ocean View And Dockage

148 Anglers Way, Islamorada, United States Show map

Situated nearly 5 minutes' walk from Windley Key Fossil Reef Geological State Park, the 2-bedroom Pristine Islamorada Pool Home With Ocean View And Dockage is ideal for up to 7 guests. 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 just 6 minutes' walk from the class museum "Florida Keys History and Discovery Center", the 3-bedroom Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! Islamorada villa… More

From US$ 1093 Book Now

Islamorada Modern Penthouse With Private Beach

80639 Old Highway, Islamorada, United States Show map

The 3-bedroom Islamorada Modern Penthouse With Private Beach villa is situated approximately 5 minutes' walk from FNX Club by Islamorada Fitness and offers guests to relax with a Jacuzzi. Offering an… More

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

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

Offering an outdoor swimming pool, the 3-bedroom Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa is situated merely 9 minutes' walk from Lobster Trap Art Gift… More

From US$ 722 Book Now

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

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

Offering karaoke for a delightful experience, Ocean Views With Secret Speakeasy Bbq Patio Dock Pool 3Br With Private Bathrooms Islamorada villa is located within a 700-metre distance of Windley Key… More

From US$ 723 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

Offering live performances for a delightful experience, Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina is located merely an 8… More

From US$ 394 Book Now

Pineapple Beach

130 Aregood Lane, Islamorada, United States Show map

Along with access to such natural sites as the 45 - acre Founders Park, approximately 25 minutes' walk away, the 5-bedroom Pineapple Beach Islamorada villa offers a swimming pool. The property… More

From US$ 2875 Book Now

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

135 Gulfview Drive, Islamorada, United States Show map

Situated approximately a 15-minute walk from Anne's Beach, Waterfront 4Br,4Ba Home - Private Pool And Beach - Golf Cart - Dock - Sleeps 9 Islamorada entices guests to explore various tourist… More

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La Dolce Vita Villa

116 Stromboli Dr, Islamorada, United States Show map

Staying at the 3-bedroom La Dolce Vita Villa Islamorada, guests can easily reach Lobster Trap Art Gift Shop and Gallery, located approximately 6 km away. This Islamorada holiday home is suitable for… More

From US$ 333 Book Now

Beacon Reef 501

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

Featuring a fitness room for active guests, Beacon Reef 501 Villa Islamorada is just a 5-minute walk from History of Diving Museum. Located fairly close to Island Community Church, this 2-bedroom… More

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Private Beach Private Overwater Dock Heated Pool Mahi Key

76321 Overseas Highway, Islamorada, United States Show map

Situated right around the corner from Lower Matecumbe Key Island, the 3-bedroom Private Beach Private Overwater Dock Heated Pool Mahi Key Islamorada villa is suitable for 6 guests and provides a… More

From US$ 2307 Book Now

Casa Mar

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

Casa Mar Villa Islamorada enjoys a convenient location, 4 km from Craig Key Island, and offers guests to unwind in a hot tub. The 3-bedroom holiday home features a heated pool and is ideal for up to… More

From US$ 657 Book Now

Is55Flr Captain'S Cove

227 El Capitan Dr, Islamorada, United States Show map

Located a 15-minute walk from Anne's Beach, Is55Flr Captain'S Cove Islamorada villa offers fitness classes, as well as a fitness room for active guests. More

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Antigua Place

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

The 3-bedroom Antigua Place Islamorada villa is located about 20 minutes on foot from Anne's Beach and allows guests to enjoy windsurfing, snorkelling, and fisheries. More

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Beacon Reef 406

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

Located around 5 minutes' walk from History of Diving Museum, the 2-bedroom Beacon Reef 406 Villa Islamorada offers a Jacuzzi for additional relaxation. Providing guests with Wi-Fi and parking, this… More

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Paradise Palms Islamorada

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

Located just an 8-minute walk from Windley Key Fossil Reef Geological State Park, the 3-bedroom Paradise Palms Islamorada villa is suitable for 8 guests and provides an outdoor swimming pool to relax… More

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Little Bay Cottage

82246 Overseas Hwy, Islamorada, United States Show map

Situated about 10 minutes' walk from Keys History & Discovery Center, the 2-bedroom Little Bay Cottage Islamorada entices guests with snorkelling, diving, and fisheries in the area. Providing guests… More

From US$ 549 Book Now

Palms 404

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

Offering a Jacuzzi for a relaxing experience, Palms 404 Villa Islamorada is located a 20-minute walk from Lignumvitae Key Botanical State Park. The 2-bedroom villa features opportunities for… More

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Lyons Landing

105 Severino Drive, Islamorada, United States Show map

Located nearly 20 minutes' walk from Rain Barrel Village, the 4-bedroom Lyons Landing Villa Islamorada has a heated pool and is ideal for up to 10 guests. Guests can enjoy windsurfing, snorkelling… More

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Martin Family Fish Camp

106 Madeira Rd., Islamorada, United States Show map

Situated around 5 minutes' walk from Lobster Trap Art Gift Shop and Gallery, the 4-bedroom Martin Family Fish Camp Villa Islamorada entices guests with windsurfing, snorkelling, and canyoning in the… More

From US$ 823 Book Now

Palms 417

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

Featuring a heated pool, the 1-bedroom Palms 417 Villa Islamorada is suitable for up to 3 people and is located around 20 minutes' walk from Indian Key State Historic Site. Providing guests with Wi… More

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Palms 317

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

During the stay at the 1-bedroom Palms 317 Villa Islamorada, guests can indulge in a Jacuzzi or visit Indian Key State Historic Site, located about 20 minutes' walk away. This 1-bathroom villa… More

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

422 Palm Dr, Islamorada, United States Show map

Nestled 2.9 km from Craig Key Island, Bayside - Islamorada Waterfront, 360 Viewing Deck, Htd Swim Spa villa entices guests to explore various tourist destinations nearby. More

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Beacon Reef 503

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

During the stay at Beacon Reef 503 Villa Islamorada, guests can indulge in a hot tub or visit the world-class museum "Florida Keys History and Discovery Center", located an 18-minute walk away. The 2… More

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Villa Riolo

130 Columbus Dr, Islamorada, United States Show map

Providing guests with an aqua park and spa therapy to ensure a memorable stay, the 2-bedroom Villa Riolo Islamorada is a few moments from Lower Matecumbe Key Island. Located about 3 km from the 280 -… More

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Oceanside Anglers Reef Home With Beach Pool And Kayaks

119 Anglers Way, Islamorada, United States Show map

Located around a 5-minute walk from Windley Key Fossil Reef Geological State Park, the 2-bedroom Oceanside Anglers Reef Home With Beach Pool And Kayaks Islamorada offers a swimming pool for guests to… More

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Sandglass 4

74980 Overseas Hwy 4, Islamorada, United States Show map

Situated around 15 minutes' walk from Lower Matecumbe Key Island, the 5-bedroom Sandglass 4 Islamorada villa provides access to numerous tourist attractions in the area. Offering windsurfing… More

From US$ 696 Book Now

Peninsula Villa Boat Dock Heated Pool Sunset Point

76414 Overseas Highway, Islamorada, United States Show map

Located just moments from Lower Matecumbe Key Island, the 6-bedroom Peninsula Villa Boat Dock Heated Pool Sunset Point Islamorada provides a swimming pool as well as snorkelling to diversify guests'… More

From US$ 1939 Book Now

Fl Keys Venetian Shores Waterfront With Ocean Access, Pool

141 Stromboli Drive, Islamorada, United States Show map

Located approximately 25 minutes' walk from the 45-acre Founders Park, Fl Keys Venetian Shores Waterfront With Ocean Access, Pool Islamorada villa has a heated pool and is ideal for up to 8 guests. More

From US$ 1011 Book Now

Palms 309

79901 Overseas Hwy., Islamorada, United States Show map

Offering a Jacuzzi for a relaxing experience, Palms 309 Villa Islamorada is located a 10-minute drive from the world-class museum "Florida Keys History and Discovery Center". The 2-bedroom villa… More

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Sirens Cove - Ocean Views, Game Room, Pool And Dock Access

84745 Old Hwy, Islamorada, United States Show map

Along with proximity to Windley Key Fossil Reef Geological State Park, located only an 8-minute stroll away, the 3-bedroom Sirens Cove - Ocean Views, Game Room, Pool And Dock Access Islamorada villa… More

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Sunshine Place

84371 Overseas Hwy, Islamorada, United States Show map

Positioned 3.4 km from bustling shopping destinations such as Lobster Trap Art Gift Shop and Gallery, the 1-bedroom Sunshine Place Islamorada villa offers guests to use parking. Located around 10… More

From US$ 384 Book Now

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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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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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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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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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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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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