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2026-10-30
2026-10-31
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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 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 Discovery… More

From US$ 200 Book Now

Hadley Resort And Marina

82749 Overseas Highway, Islamorada, United States Show map

Offering an outdoor swimming pool, the 3-star Hadley Resort And Marina Islamorada is nestled in the entertainment district of Islamorada, a 19-minute stroll from Upper Matecumbe Key Island. Featuring… More

From US$ 147 Book Now

Amara Cay Resort

80001 Overseas Highway, Islamorada, United States Show map

Located within 3 km of Upper Matecumbe Key Island, the beachfront Amara Cay Resort Islamorada includes a sun deck, playground, and a golf course. More

From US$ 266 Book Now

The Islands Of Islamorada

82779 Old Highway, Islamorada, United States Show map

The 5-star The Islands Of Islamorada hotel, located in the cultural district of Islamorada, approximately a 20-minute walk from Hurricane Monument, features views of the pool. Boasting a location a… More

From US$ 721 Book Now

Casa Morada

136 Madeira Road, Islamorada, United States Show map

Situated around a 25-minute stroll from Hurricane Monument, the comfortable 5-star Casa Morada Hotel Islamorada can arrange guided snorkelling trips to ensure a more exciting holiday. Boasting a… More

From US$ 677 Book Now

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, United States Show map

The 4-star beachfront La Siesta Resort & Villas Islamorada, located in an entertainment area, offers Wi-Fi throughout the property, an outdoor swimming pool and a fitness area. Featuring a lobby area… More

From US$ 232 Book Now

Islander Resort

82100 Overseas Highway, Islamorada, United States Show map

The 4-star luxury Islander Resort Islamorada, located in a cultural neighbourhood, also stands within 25 minutes' walk of Hurricane Monument and provides guided tour service for better sightseeing. 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 Whale Harbor Marina and offers 45 rooms with views of the pool. Featuring a heated pool, the 3… More

From US$ 149 Book Now

Bayside Villas By Islander Resort

81450 Overseas Highway, Islamorada, United States Show map

Offering access to Hurricane Monument, which is only 0.9 km away, the contemporary 4-star Bayside Villas By Islander Resort Islamorada features a sundeck and a picnic area. The luxurious resort is… More

From US$ 191 Book Now

Sunset Inn

82200 Overseas Highway, Islamorada, United States Show map

The 3-star Sunset Inn Islamorada, located merely 5 minutes' walk from the class museum "Florida Keys History and Discovery Center" and a mere 1.3 km from Gallery Morada, features a year-round outdoor… More

From US$ 107 Book Now

Drop Anchor Resort & Marina

84959 Overseas Highway, Islamorada, United States Show map

Located around a 20-minute walk from Wilson Key, the 3-star Drop Anchor Resort & Marina Islamorada boasts a heated pool. Featuring 18 rooms with views of the sea, the resort is 2.8 km from Rain… More

From US$ 343 Book Now

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

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

76400 Overseas Highway, Islamorada, United States Show map

Situated just moments from Lower Matecumbe Key Island, 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 is located in Islamorada, 15 minutes' walk from History of Diving Museum, and offers a swimming pool. The hotel offers Wi-Fi throughout the property. More

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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

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

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

Located only a 6-minute walk from the world-class museum "Florida Keys History and Discovery Center", the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location… More

From US$ 1360 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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Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

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

Located merely a 9-minute walk from Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa features an outdoor… 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

Located just 1 km from Michelle Nicole Lowe Art Gallery, the 3-bedroom Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa has a heated pool and is ideal for… More

From US$ 587 Book Now

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

Beachfront Estate - Two Villas Heated Pools Docks Dolphin Mahi Key

76311 & 76321 Overseas Highway, Islamorada, United States Show map

The 7-bedroom Beachfront Estate - Two Villas Heated Pools Docks Dolphin Mahi Key Islamorada hosts up to 14 guests and provides proximity to Lower Matecumbe Key Island, situated only 5 minutes' walk… 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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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

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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Private Beach Heated Pool Private Dock Dolphin Key

76311 Overseas Highway, Islamorada, United States Show map

Situated in the immediate vicinity of Lower Matecumbe Key Island, Private Beach Heated Pool Private Dock Dolphin Key Islamorada villa offers guests to relax by a heated pool. Located a 10-minute ride… More

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Little Bay Prime

82246 Overseas Highway, Islamorada, United States Show map

The 4-bedroom Little Bay Prime Apartment Islamorada boasts a beachfront setting and in about 10 minutes' walk from Keys History & Discovery Center. Offering an aqua park and spa therapy, this… More

From US$ 1510 Book Now

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

Santorini- Islamorada Waterfront Condo, Ensuites, Pool, Hot Tub

101 Gulfview Dr Apt 202, Islamorada, United States Show map

To enjoy your vacation in Islamorada, stay at the 2-bedroom Santorini- Islamorada Waterfront Condo, Ensuites, Pool, Hot Tub, which is nearly a 15-minute walk from Anne's Beach and 3.5 km from Craig… 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

Private Beach Heated Pool Volleyball Court Orchid Beach Key

77145 Overseas Hwy, Islamorada, United States Show map

Located nearly 20 minutes' walk from Indian Key Historic State Park, the 4-bedroom Private Beach Heated Pool Volleyball Court Orchid Beach Key Islamorada villa boasts an outdoor swimming pool with a… More

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Florida Keys Boat Charters

85920 Overseas Highway, Islamorada, United States Show map

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From US$ 324 Book Now

Luxury 3Br Coastal Escape In Islamorada

80639 Old Highway, Apt 309, Islamorada, United States Show map

The 2275 m² Luxury 3Br Coastal Escape In Islamorada apartment is 17 minutes' walk from Gallery Morada and provides spa facilities such as a hot tub and a sauna. Situated within a few blocks of Indian… 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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Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location

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

Located merely 1.2 km from Upper Matecumbe Key Island, the 3-bedroom Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa has an outdoor swimming pool and is… 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-bedroom Little Bay Lower Islamorada apartment, which is 2.2 km from Lignumvitae Key Botanical State Park and just 12 minutes' walk from Lobster… More

From US$ 621 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 Lower Matecumbe Key… 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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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 heated pool, the 4-bedroom Waterfront Private Home, Pool, Dock, Sunsets, Tiki Islamorada is located about 5 minutes' walk from Michelle Nicole Lowe Art Gallery and is suitable for up to 7… More

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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

To enjoy your vacation in Islamorada, stay at the spacious 188 m² Ocean View Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key Two Islamorada apartment, which is only 1.2 km from Anne's… 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

The spacious Ocean View Two Duplex Penthouses Retreat Amenities: Tennis Court Heated Pool Vista Key Islamorada is located 3.6 km from Craig Key Island and a 15-minute stroll from Anne's Beach. Wi-Fi… More

From US$ 1899 Book Now

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

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

Situated only 8 minutes' walk from Windley Key Fossil Reef Geological State Park, the 3-bedroom Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool Islamorada villa entices guests with snorkelling,… More

From US$ 1403 Book Now