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2026-08-01
2026-08-02
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Pet-friendly hotels in Islamorada

Sands Of Islamorada

80051 Overseas Highway, Islamorada, United States Show map

Located about 10 minutes by car from the Lobster Trap Art Gift Shop and Gallery, Sands Of Islamorada hotel offers air-conditioned rooms 3.4 km from the class museum "Florida Keys History and… More

From US$ 187 Book Now

Hadley Resort And Marina

82749 Overseas Highway,, Islamorada, United States Show map

Offering various recreational opportunities and barbecue, the smoke-free Hadley Resort And Marina Islamorada lies in an entertainment area of Islamorada, a 19-minute walk from the Upper Matecumbe Key… More

From US$ 147 Book Now

Amara Cay Resort

80001 Overseas Highway, Islamorada, United States Show map

The comfortable Amara Cay Resort Islamorada offers access to the Upper Matecumbe Key, which is located around 3 km away. The 4-star beachfront hotel has a heated swimming pool along with a tiki bar… More

From US$ 266 Book Now

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, United States Show map

Located merely 1.2 km from the Indian Key State Historic Site, the 4-star beachfront La Siesta Resort & Villas Islamorada offers amenities such as various recreational opportunities and watersports… More

From US$ 232 Book Now

Casa Morada

136 Madeira Road, Islamorada, United States Show map

Boasting the chance to relax by Barley Basin, situated approximately a 20-minute stroll away, the comfortable 5-star Casa Morada Hotel Islamorada also invites guests to go fishing. Featuring a heated… More

From US$ 464 Book Now

Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort

84457 Overseas Highway, Islamorada, United States Show map

The charming 4-star Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort, located just 1.2 km from the Windley Key Fossil Reef Geological State Park, offers 3 outdoor swimming pools… More

From US$ 180 Book Now

Islander Resort

82100 Overseas Highway, Islamorada, United States Show map

The 4-star luxury Islander Resort Islamorada is located within 25 minutes' walk of the Hurricane Monument and offers guided tour service for better sightseeing in Islamorada. Boasting a location a… More

From US$ 204 Book Now

Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, United States Show map

The oceanfront Chesapeake Beach Resort Islamorada enjoys a private location about 5 minutes' walk from the Whale Harbor Marina and offers 45 rooms with views of the pool. Featuring a heated pool, the… More

From US$ 149 Book Now

Bayside Villas By Islander Resort

81450 Overseas Highway, Islamorada, United States Show map

The contemporary 4-star Bayside Villas By Islander Resort Islamorada is situated only 600 metres from the Indian Key State Historic Site and boasts a sun deck and a picnic area. Boasting a heated… More

From US$ 191 Book Now

Sunset Inn

82200 Overseas Highway, Islamorada, United States Show map

Offering air-conditioned rooms and Wi-Fi in public areas, the smoke-free Sunset Inn Islamorada is only 1.3 km from the Gallery Morada and merely an 11-minute walk from the Upper Matecumbe Key. More

From US$ 107 Book Now

Drop Anchor Resort & Marina

84959 Overseas Highway, Islamorada, United States Show map

The 3-star Drop Anchor Resort & Marina Islamorada offers air-conditioned rooms around a 20-minute walk from Wilson Key. Located 2.8 km from the Rain Barrel Sculpture Gallery, this lovely resort… More

From US$ 274 Book Now

Margaritaville

87380 Overseas Highway, Islamorada, United States Show map

Margaritaville Islamorada villa is located 25 minutes' walk from the 45 - acre Founders Park and invites guests to enjoy a terrace. The 2-bedroom holiday home hosts up to 6 guests and provides them… More

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Executive Bay Islamorada By Sofla Vacations

87200 Overseas Highway, Islamorada, United States Show map

Offering sea views, Executive Bay Islamorada By Sofla Vacations villa is situated only 0.7 km from the Rain Barrel Sculpture Gallery. This 8-room holiday home features opportunities for snorkelling… More

From US$ 150 Book Now

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

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

Located merely a 7-minute walk from the Windley Key Fossil Reef Geological State Park, At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa offers snorkelling, ping pong, and… More

From US$ 467 Book Now

Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key

76400 Overseas Highway, Islamorada, United States Show map

Situated a few steps from the Lower Matecumbe Key, the elegant Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key Islamorada hotel offers air-conditioned rooms, Wi-Fi… More

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Casa Morada

136 Madeira Road, Islamorada, United States Show map

Casa Morada Hotel Islamorada, located 5 minutes on foot from the Lobster Trap Art Gift Shop and Gallery and just 1.3 km from the History of Diving Museum, features a swimming pool for guests to take… More

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Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

Offering sea views, Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa is situated 650 metres from the Windley Key Fossil Reef Geological State Park. The 3-bedroom holiday home hosts… 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

The 3-bedroom Isla Key Acai - 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$ 896 Book Now

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

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

Situated just 500 m from the class museum "Florida Keys History and Discovery Center", the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa is… 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

The 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa accommodates up to 6 guests and offers proximity to the Lobster Trap Art Gift Shop and Gallery… More

From US$ 590 Book Now

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

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

Situated just 1 km from the Michelle Nicole Lowe Art Gallery, the 3-bedroom Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa entices guests to explore… More

From US$ 587 Book Now

Heart Of Morada

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

At the 3-bedroom Heart Of Morada Villa Islamorada, guests can enjoy canoeing and cycling as well as a location nearly 5 minutes' walk from the Hurricane Monument. More

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Private Beach Private Overwater Dock Heated Pool Mahi Key

76321 Overseas Highway, Islamorada, United States Show map

Located just around the corner from the Lower Matecumbe Key, the 3-bedroom Private Beach Private Overwater Dock Heated Pool Mahi Key Islamorada villa offers opportunities for snorkelling in the area. More

From US$ 1956 Book Now

Antigua Place

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

Staying at the 3-bedroom Antigua Place Islamorada villa, guests can visit Anne's Beach, which is only 1.8 km away. Offering windsurfing, snorkelling, and fishing, the Islamorada holiday home is… More

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Lyons Landing

105 Severino Drive, Islamorada, United States Show map

The 4-bedroom Lyons Landing Villa Islamorada is located approximately 20 minutes' walk from the Rain Barrel Village and welcomes its guests to enjoy windsurfing, snorkelling, and diving. More

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Martin Family Fish Camp

106 Madeira Rd., Islamorada, United States Show map

At the 4-bedroom Martin Family Fish Camp Villa Islamorada, guests can enjoy windsurfing, snorkelling, and canoeing as well as a location about 5 minutes' walk from the Lobster Trap Art Gift Shop and… More

From US$ 823 Book Now

Villa Riolo

130 Columbus Dr, Islamorada, United States Show map

Situated right around the corner from the Lower Matecumbe Key, the 2-bedroom Villa Riolo Islamorada is ideal for up to 6 guests. More

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Little Bay Prime

82246 Overseas Highway, Islamorada, United States Show map

The 4-room Little Bay Prime Apartment Islamorada enjoys a beachfront location around a 10-minute walk from the Keys History & Discovery Center. The maximum occupancy at this apartment is 12 guests. More

From US$ 1510 Book Now

Sandglass 4

74980 Overseas Hwy 4, Islamorada, United States Show map

Situated about 15 minutes' walk from the Lower Matecumbe Key, the 5-bedroom Sandglass 4 Islamorada villa provides access to numerous tourist attractions in the area. Suitable for up to 12 guests, the… More

From US$ 696 Book Now

Peninsula Villa Boat Dock Heated Pool Sunset Point

76414 Overseas Highway, Islamorada, United States Show map

The 6-bedroom Peninsula Villa Boat Dock Heated Pool Sunset Point Islamorada hosts up to 12 guests and provides proximity to the Lower Matecumbe Key, situated only a 5-minute stroll away. Guests can… 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 swimming pool and is ideal for up to 8 guests.… More

From US$ 1011 Book Now

Sunshine Place

84371 Overseas Hwy, Islamorada, United States Show map

Accommodating up to 3 guests, the 1-bedroom Sunshine Place Islamorada villa is situated 3.8 km from renowned cultural sites such as the Rain Barrel Sculpture Gallery. The property features… More

From US$ 384 Book Now

Florida Keys Boat Charters

85920 Overseas Highway, Islamorada, United States Show map

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From US$ 324 Book Now

Little Bay Compound

82246 Overseas Highway, Islamorada, United States Show map

Featuring an indoor water park and a wellness centre, the 6-bedroom Little Bay Compound Villa Islamorada offers guests to enjoy a beachfront location only 10 minutes' walk from the Keys History &… 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

The 3-bedroom Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa is located a mere 1.2 km from the Upper Matecumbe Key, giving access to various tourist… More

From US$ 605 Book Now

Little Bay Lower

82246 Overseas Hwy, Islamorada, United States Show map

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

From US$ 621 Book Now

Snorkel In Islamorada'S Clear Blue Waters

85920 Overseas Highway, Islamorada, United States Show map

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The Oasis

82703 Old Highway, Islamorada, United States Show map

Hosting up to 8 guests, The Oasis Villa Islamorada is nestled in a beach area, only 1.7 km from Anne s Beach. Guests can enjoy snorkelling, canoeing, and cycling at this 3-bedroom villa, located 10… More

From US$ 1964 Book Now

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 the Lower Matecumbe Key… 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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Waterfront Private Home, Pool, Dock, Sunsets, Tiki

81912 Overseas Highway, Islamorada, United States Show map

Featuring a hot tub, the 4-bedroom Waterfront Private Home, Pool, Dock, Sunsets, Tiki Islamorada is located merely 7 minutes' walk from the Hurricane Monument and can host up to 7 guests. Providing… More

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Straight To The Islamorada Sandbar Charters

85920 Overseas Highway, Islamorada, United States Show map

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Florida Keys Boat Trips Multi Activity

85920 Overseas Highway, Islamorada, United States Show map

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From US$ 342 Book Now

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

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

The spacious 188 m² Ocean View Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key Two Islamorada apartment is a good choice for accommodating up to 6 guests, offering a convenient… 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

Located 25 minutes' walk from the Lower Matecumbe Key, the spacious Ocean View Two Duplex Penthouses Retreat Amenities: Tennis Court Heated Pool Vista Key Islamorada overlooks the sea. Boasting a… More

From US$ 1899 Book Now

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 accommodates up to 6 guests and offers proximity to the Windley Key Fossil Reef Geological State Park, located merely an 8… More

From US$ 1403 Book Now