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2026-08-03
2026-08-04
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Hotels in Upper Matecumbe Key area of Islamorada

Heart Of Morada

81906 Overseas Highway #3, Islamorada, United States Show map

The 3-bedroom Heart Of Morada Villa Islamorada is located about a 20-minute walk from the Lignumvitae Key Botanical State Park and provides canoeing and cycling for active guests. 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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Little Basin Villas

84 Johnston Road, Islamorada, United States Show map

Situated nearly a 5-minute stroll from Elena Madden Studio Gallery, the 9-room Little Basin Villas Islamorada offers quick access to numerous city landmarks nearby. More

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Cheeca Lodge & Spa

81801 Overseas Highway Mile Marker 82, Islamorada, United States Show map

Proud to offer 10 outdoor tennis courts, the exclusive 5-star Cheeca Lodge & Spa Islamorada hotel lies only 500 metres from the Gallery Morada in a cultural area. Located in proximity to the… More

From US$ 185 Book Now

The Caribbean Resort

117 South Carroll Street, Islamorada, United States Show map

Offering a swimming pool, the smoke-free The Caribbean Resort Islamorada is nestled in the cultural district of Islamorada, around a 10-minute walk from the Gallery Morada. Located just a few steps… More

From US$ 550 Book Now

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

Off The Charts-Waterfront Tiki Bar & Private Dock

110 Madeira Road, Islamorada, United States Show map

Situated about 5 minutes' walk from the Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Off The Charts-Waterfront Tiki Bar & Private Dock Villa Islamorada is ideal for up to 6 guests. Providing… More

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Islander Resort

82100 Overseas Highway, Islamorada, United States Show map

The 4-star Islander Resort Islamorada is situated in the cultural district of Islamorada, around a 20-minute walk from the Indian Key State Historic Site and features 114 rooms with views of the sea.… More

From US$ 204 Book Now

The Moorings Village

123 Beach Rd, Islamorada, United States Show map

The 3-star The Moorings Village Islamorada hotel, located just 9 minutes' walk from the Michelle Nicole Lowe Art Gallery and around 300 metres from Anne s Beach, features a heated swimming pool for… More

From US$ 459 Book Now

Casa Morada

136 Madeira Road, Islamorada, United States Show map

The elegant Casa Morada Hotel Islamorada, located a mere 1.1 km from Anne s Beach, offers a swimming pool, Wi-Fi throughout the property. The 5-star hotel is a good starting point for exploring… More

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Sunset Inn

82200 Overseas Highway, Islamorada, United States Show map

Nestled only 0.7 km from the Lobster Trap Art Gift Shop and Gallery, the comfortable 3-star Sunset Inn Islamorada welcomes guests with a picnic area and barbecue grills. Featuring an outdoor swimming… More

From US$ 107 Book Now

La Jolla Resort

82216 Overseas Highway, Islamorada, United States Show map

Situated only 7 minutes' walk from the Lobster Trap Art Gift Shop and Gallery, the charming La Jolla Resort Islamorada offers a picnic area and barbecue grills. Located on a private beach, this 2… More

From US$ 181 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

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

84 Johnston Avenue Unit #4, Islamorada, United States Show map

Staying at the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa, guests can visit the Hurricane Monument, which is approximately a 15-minute… More

From US$ 1360 Book Now

Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

84 Johnston Ave Unit #3, Islamorada, United States Show map

Located within 25 minutes' walk of the Indian Key State Historic Site, the 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa provides access to various… More

From US$ 590 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

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

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

84 Johnston Ave Unit #2, Islamorada, United States Show map

The 3-bedroom Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa hosts up to 6 guests and provides proximity to the Lobster Trap Art Gift Shop and Gallery… More

From US$ 587 Book Now

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

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

Situated approximately a 15-minute walk from the Upper Matecumbe Key, the 3-bedroom Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa entices guests to… More

From US$ 605 Book Now

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

84 Johnston Ave Unit #1, Islamorada, United States Show map

Located around a 25-minute walk from the Indian Key State Historic Site, Isla Honeydew - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa gives access to various tourist sites in… More

From US$ 957 Book Now

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

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

Staying at Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa, guests can visit the Hurricane Monument, which is just 1.2 km away. More

From US$ 872 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

Little Bay Lower

82246 Overseas Hwy, Islamorada, United States Show map

Little Bay Lower Islamorada apartment is located just 1 km from the Lobster Trap Art Gift Shop and Gallery and a 17-minute walk from the Upper Matecumbe Key. This apartment capacity is based on up to… More

From US$ 621 Book Now

Little Bay Prime

82246 Overseas Highway, Islamorada, United States Show map

Little Bay Prime Apartment Islamorada features a beachfront location 10 minutes' walk from the History of Diving Museum and hosts up to 12 guests. Wi-Fi is provided for both business and leisure… More

From US$ 1510 Book Now

Little Bay Upper

82246 Overseas Hwy, Islamorada, United States Show map

To enjoy your vacation in Islamorada, stay at the 2-room Little Bay Upper Apartment Islamorada, which is just 12 minutes' walk from the Lobster Trap Art Gift Shop and Gallery and a mere 1.4 km from… More

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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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Bayside Villas By Islander Resort

81450 Overseas Highway, Islamorada, United States Show map

Featuring a restaurant, the 4-star luxurious Bayside Villas By Islander Resort Islamorada lies 600 m from the Lignumvitae Key Botanical State Park. Boasting access to the History of Diving Museum… More

From US$ 191 Book Now

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

Hadley Resort And Marina

82749 Overseas Highway,, Islamorada, United States Show map

The comfortable 3-star Hadley Resort And Marina Islamorada, located just a 13-minute stroll from the Lobster Trap Art Gift Shop and Gallery, offers an outdoor swimming pool and Wi-Fi throughout the… More

From US$ 147 Book Now

The Islands Of Islamorada

82779 Old Highway, Islamorada, United States Show map

Located in the beach area of Islamorada, the comfortable 4-star The Islands Of Islamorada hotel offers air-conditioned rooms with tea and coffee making facilities. Boasting a swimming pool, this… More

From US$ 2000 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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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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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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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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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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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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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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Beacon Reef #204

83201 Old Highway, Islamorada, United States Show map

The spacious 118 m² Beacon Reef #204 Apartment Islamorada lies in a beach area, only 1.7 km from the class museum "Florida Keys History and Discovery Center" and nearly 25 minutes on foot from the… More

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Pines & Palms Resort

80401 Old Highway, Islamorada, United States Show map

Located 3 km from the Lobster Trap Art Gift Shop and Gallery, Pines & Palms Resort Islamorada includes 24 rooms with views of the sea. Located on a private beach, the hotel comes with a car park on… More

From US$ 134 Book Now

Sands Of Islamorada

80051 Overseas Highway, Islamorada, United States Show map

Located about a 25-minute stroll from the Indian Key State Historic Site, the 2-star Sands Of Islamorada hotel offers Wi-Fi in public areas and a car park. Boasting an outdoor swimming pool, this… More

From US$ 187 Book Now

Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, United States Show map

Located just 0.9 km from the History of Diving Museum, the 3-star Chesapeake Beach Resort Islamorada is only a 5-minute walk from the Whale Harbor Marina. Featuring 45 rooms with views of the sea… More

From US$ 149 Book Now

Breezy Palms Resort

80015 Overseas Highway, Islamorada, United States Show map

The comfortable 3-star Breezy Palms Resort Islamorada, located just 1.4 km from the Lignumvitae Key Botanical State Park, offers an outdoor swimming pool, Wi-Fi throughout the property. This… More

From US$ 142 Book Now

Amara Cay Resort

80001 Overseas Highway, Islamorada, United States Show map

Located in the beachfront, 3 km from the Upper Matecumbe Key, the family-friendly Amara Cay Resort Islamorada boasts a sun terrace, a golf course, and a living area. This 4-star hotel features 110… More

From US$ 266 Book Now