Best Islamorada Vacation Rentals
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Private beach
Anglers Reef Vacation Rental
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Pool with view
Situated 6 minutes' walk from Windley Key Island, Anglers Reef Vacation Rental Islamorada villa entices guests with views of the garden. Suitable for 6 guests, the 2-bedroom villa offers canyoning, cycling, and fisheries to diversify guests' leisure.
Anglers Reef Vacation Rental villa also provides a heated pool, overlooking the beach.
Anglers Reef Vacation Rental
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Pool with view
Anglers Reef Vacation Rental
Situated 6 minutes' walk from Windley Key Island, Anglers Reef Vacation Rental Islamorada villa entices guests with views of the garden. Suitable for 6 guests, the 2-bedroom villa offers canyoning, cycling, and fisheries to diversify guests' leisure.
Anglers Reef Vacation Rental villa also provides a heated pool, overlooking the beach.
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Beach access
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Outdoor swimming pool
The 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa is nestled a mere 6 minutes' walk from the class museum "Florida Keys History and Discovery Center" and can accommodate up to 6 guests.
An outdoor swimming pool is featured at Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable villa, as well as opportunity to participate in fitness classes.
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Outdoor swimming pool
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
The 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa is nestled a mere 6 minutes' walk from the class museum "Florida Keys History and Discovery Center" and can accommodate up to 6 guests.
An outdoor swimming pool is featured at Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable villa, as well as opportunity to participate in fitness classes.
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Top location
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Beach access
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Outdoor swimming pool
Located approximately 15 minutes' walk from Upper Matecumbe Key Island, the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa has an outdoor swimming pool and is ideal for up to 6 guests.
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Outdoor swimming pool
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Located approximately 15 minutes' walk from Upper Matecumbe Key Island, the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa has an outdoor swimming pool and is ideal for up to 6 guests.
Cheap Islamorada Vacation Rentals
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Private beach
Turtle Nest Estate
- BBQ facilities
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Open-air bath
- Saltwater pool
Turtle Nest Estate Villa Islamorada is situated only a 5-minute walk from the Lower Matecumbe Key and provides a Jacuzzi for additional comfort.
There are also snorkelling, diving, and fishing for guests' leisure.
Turtle Nest Estate
- BBQ facilities
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Open-air bath
- Saltwater pool
Turtle Nest Estate
Turtle Nest Estate Villa Islamorada is situated only a 5-minute walk from the Lower Matecumbe Key and provides a Jacuzzi for additional comfort.
There are also snorkelling, diving, and fishing for guests' leisure.
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Beach access
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Heated swimming pool
Staying at the 3-bedroom Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa, guests can easily reach Gallery Morada, located just 1.4 km away. The Islamorada villa features an outdoor swimming pool and is ideal for up to 6 guests.
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Heated swimming pool
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
Staying at the 3-bedroom Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa, guests can easily reach Gallery Morada, located just 1.4 km away. The Islamorada villa features an outdoor swimming pool and is ideal for up to 6 guests.
Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Outdoor swimming pool
Situated only a 9-minute stroll from Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa is suitable for 6 guests and provides an outdoor swimming pool to relax in. Offering Wi-Fi, the Islamorada villa is located in the vicinity of History of Diving Museum.
Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Outdoor swimming pool
Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
Situated only a 9-minute stroll from Lobster Trap Art Gift Shop and Gallery, the 3-bedroom Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa is suitable for 6 guests and provides an outdoor swimming pool to relax in. Offering Wi-Fi, the Islamorada villa is located in the vicinity of History of Diving Museum.
Pet Friendly Vacation Rentals Islamorada
Beachfront Villa At Islamorada By The Glamhomes
- Flat-screen TV
Beachfront Villa At Islamorada By The Glamhomes is located a 5-minute walk from the Lower Matecumbe Key and offers guests to enjoy canoeing. The 4-bedroom villa includes free private parking and a terrace with views of the sea.
You can indulge in an outdoor swimming pool or rent cars and explore the beauty of Islamorada.
Beachfront Villa At Islamorada By The Glamhomes
- Flat-screen TV
Beachfront Villa At Islamorada By The Glamhomes
Beachfront Villa At Islamorada By The Glamhomes is located a 5-minute walk from the Lower Matecumbe Key and offers guests to enjoy canoeing. The 4-bedroom villa includes free private parking and a terrace with views of the sea.
You can indulge in an outdoor swimming pool or rent cars and explore the beauty of Islamorada.
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Great deal
Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Massage
- Heated swimming pool
Featuring a terrace and a swimming pool, Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key Islamorada hotel lies 10 minutes' drive from Anne's Beach. This resort offers Wi-Fi throughout the property.
Guests will enjoy access to a games room provided for their entertainment.
Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Massage
- Heated swimming pool
Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key
Featuring a terrace and a swimming pool, Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key Islamorada hotel lies 10 minutes' drive from Anne's Beach. This resort offers Wi-Fi throughout the property.
Guests will enjoy access to a games room provided for their entertainment.
Off The Charts-Waterfront Tiki Bar & Private Dock
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun terrace
Nestled 14 minutes' walk from Hurricane Monument, Off The Charts-Waterfront Tiki Bar & Private Dock Villa Islamorada entices guests to explore various tourist destinations nearby. The 3-bedroom villa hosts up to 6 guests and provides them with private parking.
Off The Charts-Waterfront Tiki Bar & Private Dock
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun terrace
Off The Charts-Waterfront Tiki Bar & Private Dock
Nestled 14 minutes' walk from Hurricane Monument, Off The Charts-Waterfront Tiki Bar & Private Dock Villa Islamorada entices guests to explore various tourist destinations nearby. The 3-bedroom villa hosts up to 6 guests and provides them with private parking.
Islamorada Vacation Rentals Oceanfront
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Beach access
Island Time - Oceanview Balconies- Dock- Htd Pool
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Heated swimming pool
Located 8 minutes' walk from Windley Key Fossil Reef Geological State Park, Island Time - Oceanview Balconies- Dock- Htd Pool Villa Islamorada offers snorkelling and fisheries to diversify guests' leisure. Providing guests with Wi-Fi and parking, the 3-bedroom villa is 3.2 km from Rain Barrel Sculpture Gallery.
A heated pool is featured at this Islamorada accommodation, as well as opportunity to participate in fitness classes.
Island Time - Oceanview Balconies- Dock- Htd Pool
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Heated swimming pool
Island Time - Oceanview Balconies- Dock- Htd Pool
Located 8 minutes' walk from Windley Key Fossil Reef Geological State Park, Island Time - Oceanview Balconies- Dock- Htd Pool Villa Islamorada offers snorkelling and fisheries to diversify guests' leisure. Providing guests with Wi-Fi and parking, the 3-bedroom villa is 3.2 km from Rain Barrel Sculpture Gallery.
A heated pool is featured at this Islamorada accommodation, as well as opportunity to participate in fitness classes.
Vacation Rental Florida Keys
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun loungers
The 2-bedroom Vacation Rental Florida Keys Marathon villa hosts up to 6 guests and is nestled just 1.6 km from natural sites such as Oceanfront Park.
Vacation Rental Florida Keys
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun loungers
Vacation Rental Florida Keys
The 2-bedroom Vacation Rental Florida Keys Marathon villa hosts up to 6 guests and is nestled just 1.6 km from natural sites such as Oceanfront Park.
Miami Getaway Heated Pool Villa With Mini Golf & Bbq
- BBQ facilities
- Free parking
- Housekeeping
- Air conditioning
- Fitness centre
- Plunge pool
The 5-bedroom Miami Getaway Heated Pool Villa With Mini Golf & Bbq is located 2.7 km from Eureka Park and provides mini golf, billiard, and darts for active guests. Featuring a Jacuzzi, this accommodation is suitable for 16 people.
The Miami property offers an access to a heated pool, as well as opportunity to participate in fitness classes.
Miami Getaway Heated Pool Villa With Mini Golf & Bbq
- BBQ facilities
- Free parking
- Housekeeping
- Air conditioning
- Fitness centre
- Plunge pool
Miami Getaway Heated Pool Villa With Mini Golf & Bbq
The 5-bedroom Miami Getaway Heated Pool Villa With Mini Golf & Bbq is located 2.7 km from Eureka Park and provides mini golf, billiard, and darts for active guests. Featuring a Jacuzzi, this accommodation is suitable for 16 people.
The Miami property offers an access to a heated pool, as well as opportunity to participate in fitness classes.
Islamorada Vacation Rentals with Private Pool
New 3 Story In Homestead- 3/2.5 Balcony & Rooftop
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Nestled 5 km from the Cauley Square Historic Village, New 3 Story In Homestead- 3/2.5 Balcony & Rooftop villa entices guests to explore various tourist destinations nearby.
New 3 Story In Homestead- 3/2.5 Balcony & Rooftop
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
New 3 Story In Homestead- 3/2.5 Balcony & Rooftop
Nestled 5 km from the Cauley Square Historic Village, New 3 Story In Homestead- 3/2.5 Balcony & Rooftop villa entices guests to explore various tourist destinations nearby.
Blue Pearl New Waterfront Haven With Heated Pool ,70 Foot Dock, And More!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Golf course
- Outdoor swimming pool
Situated nearly a 5-minute walk from Florida Keys Aquarium Encounters, the 4-bedroom Blue Pearl New Waterfront Haven With Heated Pool ,70 Foot Dock, And More! Marathon villa provides bicycles for guests' fitness needs. Enticing guests with an aqua park and a golf course, the property is situated 4.1 km from Conch-Air Florida Keys Scenic Flights.
There is an outdoor swimming pool to relax, as well as cycling and fisheries.
Blue Pearl New Waterfront Haven With Heated Pool ,70 Foot Dock, And More!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Golf course
- Outdoor swimming pool
Blue Pearl New Waterfront Haven With Heated Pool ,70 Foot Dock, And More!
Situated nearly a 5-minute walk from Florida Keys Aquarium Encounters, the 4-bedroom Blue Pearl New Waterfront Haven With Heated Pool ,70 Foot Dock, And More! Marathon villa provides bicycles for guests' fitness needs. Enticing guests with an aqua park and a golf course, the property is situated 4.1 km from Conch-Air Florida Keys Scenic Flights.
There is an outdoor swimming pool to relax, as well as cycling and fisheries.
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Guest favorite
Farmhouse Miami
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Saltwater pool
Staying at the 3-bedroom Farmhouse Miami villa, guests can visit the outdoor sculptures "Coral Castle", which is approximately 6 km away.
Farmhouse Miami
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Saltwater pool
Farmhouse Miami
Staying at the 3-bedroom Farmhouse Miami villa, guests can visit the outdoor sculptures "Coral Castle", which is approximately 6 km away.
The Tropical Paradise Villa
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Billiard tables
- Pool with view
Located approximately 25 minutes on foot from Eureka Park, the 5-bedroom The Tropical Paradise Villa Miami provides access to a heated pool. Hosting up to 12 guests, the Miami villa offers a convenient location 3.3 km from Cauley Square Historic Village.
If you would like to stay active, try billiard at the Miami property.
The Tropical Paradise Villa
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Billiard tables
- Pool with view
The Tropical Paradise Villa
Located approximately 25 minutes on foot from Eureka Park, the 5-bedroom The Tropical Paradise Villa Miami provides access to a heated pool. Hosting up to 12 guests, the Miami villa offers a convenient location 3.3 km from Cauley Square Historic Village.
If you would like to stay active, try billiard at the Miami property.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Islamorada, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Anglers Reef Vacation Rental |
9.8 / 10 (4 Reviews) |
From 365$ | |
| Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable |
10.0 / 10 (1 Reviews) |
From 590$ | |
| Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location |
9.5 / 10 (2 Reviews) |
From 1360$ | |
| Turtle Nest Estate |
10.0 / 10 (1 Reviews) |
From 1716$ | |
| Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location |
10.0 / 10 (1 Reviews) |
From 587$ |
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