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2026-11-03
2026-11-04
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Pet-friendly hotels in Islamorada

Sands Of Islamorada

80051 Overseas Highway, Islamorada, United States Show map

Located about a 25-minute stroll from 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$ 200 Book Now

Hadley Resort And Marina

82749 Overseas Highway, Islamorada, United States Show map

Located only a 13-minute stroll from Lobster Trap Art Gift Shop and Gallery, the charming 3-star Hadley Resort And Marina Islamorada offers Wi-Fi throughout the property and a car park. Boasting an… More

From US$ 147 Book Now

Amara Cay Resort

80001 Overseas Highway, Islamorada, United States Show map

Offering a sunbathing terrace, playground, and a golf course, the 4-star Amara Cay Resort Islamorada is situated in Islamorada, about 3 km from Upper Matecumbe Key Island. The resort lies 10 minutes'… More

From US$ 266 Book Now

The Islands Of Islamorada

82779 Old Highway, Islamorada, United States Show map

Located in the beach area of Islamorada, the comfortable 5-star The Islands Of Islamorada hotel offers air-conditioned rooms with tea and coffee making equipment. This Islamorada hotel is in a… More

From US$ 945 Book Now

Casa Morada

136 Madeira Road, Islamorada, United States Show map

Situated around 5 minutes' walk from a beach, the 5-star boutique-style Casa Morada Hotel Islamorada offers rooms with views of the patio. Offering snorkelling, kayaking, and boating in the area… More

From US$ 677 Book Now

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, United States Show map

Located 3.1 km from Lobster Trap Art Gift Shop and Gallery, the 4-star La Siesta Resort & Villas Islamorada offers air-conditioned rooms nearly a 25-minute walk from Gallery Morada. This Islamorada… More

From US$ 232 Book Now

Islander Resort

82100 Overseas Highway, Islamorada, United States Show map

Offering a sundeck, a veranda, and grill, as well as the views of the sea, the 4-star Islander Resort Islamorada is located approximately a 20-minute walk from Indian Key State Historic Site. The… More

From US$ 204 Book Now

Chesapeake Beach Resort

83409 Overseas Highway, Islamorada, United States Show map

The 3-star Chesapeake Beach Resort Islamorada offers air-conditioned rooms about a 10-minute walk from Wilson Key. Located around 5 km from Rain Barrel Sculpture Gallery, the hotel offers views of… More

From US$ 149 Book Now

Bayside Villas By Islander Resort

81450 Overseas Highway, Islamorada, United States Show map

The 4-star luxurious Bayside Villas By Islander Resort Islamorada sits just 7 minutes' walk from Lignumvitae Key Botanical State Park and offers a restaurant. Boasting access to History of Diving… More

From US$ 191 Book Now

Sunset Inn

82200 Overseas Highway, Islamorada, United States Show map

The comfortable 3-star Sunset Inn Islamorada is approximately 700 metres from Islander resort and offers a year-round outdoor swimming pool. The inn is a good starting point for exploring Islamorada,… More

From US$ 107 Book Now

Drop Anchor Resort & Marina

84959 Overseas Highway, Islamorada, United States Show map

The 3-star oceanfront Drop Anchor Resort & Marina Islamorada is located merely 100 metres from Windley Key Fossil Reef Geological State Park, offering 18 rooms, Wi-Fi, and parking. Boasting a heated… More

From US$ 343 Book Now

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

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

Situated just 500 metres from Windley Key Fossil Reef Geological State Park, the 3-bedroom At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa is suitable for 6 guests and provides… More

From US$ 467 Book Now

Casa Morada

136 Madeira Road, Islamorada, United States Show map

The elegant Casa Morada Hotel Islamorada, located merely 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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Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key

76400 Overseas Highway, Islamorada, United States Show map

The elegant Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key Islamorada hotel, located nearly a 5-minute walk from Lower Matecumbe Key Island and 3.8 km from San Pedro… More

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

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

Situated just 9 minutes' stroll from Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa is suitable… 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

Staying at the 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa, guests can visit Indian Key State Historic Site, which is nearly a 25-minute walk away.… More

From US$ 590 Book Now

Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool

84745 Old Hwy 11, Islamorada, United States Show map

Situated only 0.7 km from Windley Key Fossil Reef Geological State Park, the 3-bedroom Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa is ideal for up to 7 guests. Providing guests… 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

Along with proximity to 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

Executive Bay Islamorada By Sofla Vacations

87200 Overseas Highway, Islamorada, United States Show map

Located just 0.7 km from Rain Barrel Village, the 2-room Executive Bay Islamorada By Sofla Vacations villa offers opportunities for snorkelling, diving, and fisheries in the area. This Islamorada… More

From US$ 150 Book Now

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

135 Gulfview Drive, Islamorada, United States Show map

Staying at Waterfront 4Br,4Ba Home - Private Pool And Beach - Golf Cart - Dock - Sleeps 9 Islamorada, guests can visit Craig Key Island, which is approximately a 10-minute ride away. More

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

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

Located just a 9-minute walk from Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa features a heated… More

From US$ 587 Book Now

Little Bay Lower

82246 Overseas Hwy, Islamorada, United States Show map

Little Bay Lower Islamorada apartment is located a mere 1 km from Lobster Trap Art Gift Shop and Gallery and a 17-minute walk from Upper Matecumbe Key Island. Wi-Fi and a car park are provided for… More

From US$ 621 Book Now

Luxury 3Br Coastal Escape In Islamorada

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

Located merely 9 minutes on foot from Lignumvitae Key Botanical State Park, the 3-bedroom Luxury 3Br Coastal Escape In Islamorada apartment accommodates up to 8 guests. The apartment enjoys a… More

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Beachfront Estate - Two Villas Heated Pools Docks Dolphin Mahi Key

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

Situated right around the corner from Lower Matecumbe Key Island, the 7-bedroom Beachfront Estate - Two Villas Heated Pools Docks Dolphin Mahi Key Islamorada is ideal for up to 14 guests. More

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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 3-bedroom Ocean View Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key Two Islamorada apartment features a convenient location nearly a 25-minute walk from Lower Matecumbe Key… More

From US$ 1446 Book Now

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

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

Located 8 minutes' walk from Windley Key Fossil Reef Geological State Park, Oceans Fourteen - Ocean View- Balconies-Dock-Htd Pool Islamorada villa is suitable for 6 guests and provides a heated pool… More

From US$ 1403 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 History of Diving Museum and hosts up to 12 guests. At this apartment, Wi-Fi and parking are also provided. More

From US$ 1510 Book Now

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

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

Located only a 9-minute walk from Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa features an… More

From US$ 605 Book Now

Villa Riolo

130 Columbus Dr, Islamorada, United States Show map

Situated just moments from Lower Matecumbe Key Island, the 2-bedroom Villa Riolo Islamorada ensures a great leisure experience by offering snorkelling, diving, and bowling. The Islamorada holiday… 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

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 around 20 minutes' walk from the 45-acre Founders Park and provides diving, canyoning, and… More

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Waterfront Private Home, Pool, Dock, Sunsets, Tiki

81912 Overseas Highway, Islamorada, United States Show map

Located 550 metres from Hurricane Monument, Waterfront Private Home, Pool, Dock, Sunsets, Tiki Islamorada is suitable for 7 guests and provides a Jacuzzi for a truly relaxing stay. This 4-bedroom… 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 Two Duplex Penthouses Retreat Amenities: Tennis Court Heated Pool Vista Key

101 Gulfview Drive Apt 314-316, Islamorada, United States Show map

Situated within 25 minutes' walk of Lower Matecumbe Key Island, the spacious 8-bedroom Ocean View Two Duplex Penthouses Retreat Amenities: Tennis Court Heated Pool Vista Key Islamorada offers a… More

From US$ 1899 Book Now

Lyons Landing

105 Severino Drive, Islamorada, United States Show map

Featuring a heated pool, Lyons Landing Villa Islamorada is suitable for up to 10 people and is located about 7 km from the world-class museum "Florida Keys History and Discovery Center". Providing… More

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

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

The spacious Santorini- Islamorada Waterfront Condo, Ensuites, Pool, Hot Tub features a prime location a 15-minute walk from Anne's Beach and hosts up to 4 guests. Wi-Fi is provided for both business… 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 Rain Barrel Sculpture Gallery, located 1.7 km away. The… More

From US$ 1011 Book Now

Martin Family Fish Camp

106 Madeira Rd., Islamorada, United States Show map

Martin Family Fish Camp Villa Islamorada is nestled only a 5-minute walk from Lobster Trap Art Gift Shop and Gallery and can accommodate up to 12 guests. Located 2.2 km from Indian Key State Historic… More

From US$ 823 Book Now

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 Lobster Trap Art Gift Shop and Gallery, located 3.4 km away. The 1-bedroom… More

From US$ 384 Book Now

Private Beach Heated Pool Volleyball Court Orchid Beach Key

77145 Overseas Hwy, Islamorada, United States Show map

Featuring an outdoor swimming pool, the 4-bedroom Private Beach Heated Pool Volleyball Court Orchid Beach Key Islamorada villa is suitable for up to 12 people and is located about a 25-minute walk… More

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Private Beach Private Overwater Dock Heated Pool Mahi Key

76321 Overseas Highway, Islamorada, United States Show map

Located just a few steps from Lower Matecumbe Key Island, the 3-bedroom Private Beach Private Overwater Dock Heated Pool Mahi Key Islamorada villa offers a swimming pool for guests to relax by. This… More

From US$ 2307 Book Now

Private Beach Heated Pool Private Dock Dolphin Key

76311 Overseas Highway, Islamorada, United States Show map

The 4-bedroom Private Beach Heated Pool Private Dock Dolphin Key Islamorada villa accommodates up to 8 guests and offers proximity to Lower Matecumbe Key Island, located merely a 5-minute walk away. More

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Antigua Place

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

Offering a location approximately 4 km from Craig Key Island, the 3-bedroom Antigua Place Islamorada villa gives access to various tourist spots in the area. The property hosts up to 6 guests and… 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

Peninsula Villa Boat Dock Heated Pool Sunset Point

76414 Overseas Highway, Islamorada, United States Show map

Offering a swimming pool, the 6-bedroom Peninsula Villa Boat Dock Heated Pool Sunset Point Islamorada is situated within easy reach of Lower Matecumbe Key Island and can accommodate up to 12 guests. More

From US$ 1939 Book Now

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

84745 Old Hwy, Islamorada, United States Show map

The 3-bedroom Sirens Cove - Ocean Views, Game Room, Pool And Dock Access Islamorada villa hosts up to 8 guests and provides proximity to Windley Key Fossil Reef Geological State Park, situated only 8… More

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Tea Table Key

79775 Overseas Highway, Islamorada, United States Show map

During the stay at the 6-bedroom Tea Table Key Villa Islamorada, guests can indulge in a Jacuzzi or visit the world-class museum "Florida Keys History and Discovery Center", located 4.4 km away. More

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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

To enjoy your vacation in Islamorada, stay at the spacious 5-bedroom Ocean View Duplex Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key One Islamorada, which is 3.5 km from Craig Key… More

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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 Keys History & Discovery Center, located nearly a 10-minute… More

Book Now