Islamorada Luxury 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
At the 2-bedroom Anglers Reef Vacation Rental Islamorada villa, guests can enjoy canoeing, cycling, and fishing as well as a location nearly a 5-minute walk from the Windley Key Fossil Reef Geological State Park. Located 2.6 km from the Rain Barrel Sculpture Gallery, the accommodation provides Wi-Fi and private car parking.
Anglers Reef Vacation Rental
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Pool with view
Anglers Reef Vacation Rental
At the 2-bedroom Anglers Reef Vacation Rental Islamorada villa, guests can enjoy canoeing, cycling, and fishing as well as a location nearly a 5-minute walk from the Windley Key Fossil Reef Geological State Park. Located 2.6 km from the Rain Barrel Sculpture Gallery, the accommodation provides Wi-Fi and private car parking.
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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 located only 1 km from the History of Diving Museum, giving access to various tourist spots nearby.
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 located only 1 km from the History of Diving Museum, giving access to various tourist spots nearby.
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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
Staying at the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa, guests can visit the Michelle Nicole Lowe Art Gallery, which is only 1 km away.
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
Staying at the 3-bedroom Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa, guests can visit the Michelle Nicole Lowe Art Gallery, which is only 1 km away.
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Private beach
Turtle Nest Estate
- BBQ facilities
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Open-air bath
- Saltwater pool
At Turtle Nest Estate Villa Islamorada, guests can enjoy snorkelling, diving, and fishing as well as a location nearly a 5-minute walk from the Lower Matecumbe Key. Offering a Jacuzzi, the accommodation is 3.6 km from Anne's Beach.
Turtle Nest Estate
- BBQ facilities
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Open-air bath
- Saltwater pool
Turtle Nest Estate
At Turtle Nest Estate Villa Islamorada, guests can enjoy snorkelling, diving, and fishing as well as a location nearly a 5-minute walk from the Lower Matecumbe Key. Offering a Jacuzzi, the accommodation is 3.6 km from Anne's Beach.
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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
Situated merely a 9-minute walk from the Lobster Trap Art Gift Shop and Gallery, Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa 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
Situated merely a 9-minute walk from the Lobster Trap Art Gift Shop and Gallery, Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa 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
The 3-bedroom Isla Key Mamey - 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, situated merely 9 minutes' walk away.
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
The 3-bedroom Isla Key Mamey - 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, situated merely 9 minutes' walk away.
Beachfront Villa At Islamorada By The Glamhomes
- Flat-screen TV
4-bedroom Beachfront Villa At Islamorada By The Glamhomes is located about a 5-minute walk from the Lower Matecumbe Key and features an outdoor swimming pool as well as a terrace for guests' pleasure. Offering Wi-Fi, this accommodation is located 3.7 km from the Indian Key Historic State Park.
Beachfront Villa At Islamorada By The Glamhomes has cars available for rent, as well as canoeing in the surrounding area.
Beachfront Villa At Islamorada By The Glamhomes
- Flat-screen TV
Beachfront Villa At Islamorada By The Glamhomes
4-bedroom Beachfront Villa At Islamorada By The Glamhomes is located about a 5-minute walk from the Lower Matecumbe Key and features an outdoor swimming pool as well as a terrace for guests' pleasure. Offering Wi-Fi, this accommodation is located 3.7 km from the Indian Key Historic State Park.
Beachfront Villa At Islamorada By The Glamhomes has cars available for rent, as well as canoeing in the surrounding area.
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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
The pet-friendly Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key Islamorada hotel, located about a 5-minute walk from the Lower Matecumbe Key and 4.4 km from Anne's Beach, features a swimming pool for guests to take a dip in. Wi-Fi is offered throughout the property at the elegant resort.
On-site entertainment venues include a games room.
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
The pet-friendly Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key Islamorada hotel, located about a 5-minute walk from the Lower Matecumbe Key and 4.4 km from Anne's Beach, features a swimming pool for guests to take a dip in. Wi-Fi is offered throughout the property at the elegant resort.
On-site entertainment venues include a games room.
Off The Charts-Waterfront Tiki Bar & Private Dock
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun terrace
The 3-bedroom Off The Charts-Waterfront Tiki Bar & Private Dock Villa Islamorada hosts up to 6 guests and provides proximity to the Lobster Trap Art Gift Shop and Gallery, situated nearly a 5-minute walk away. Providing guests with Wi-Fi and a private parking lot, the villa is a mere 1.1 km from the Hurricane Monument.
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
The 3-bedroom Off The Charts-Waterfront Tiki Bar & Private Dock Villa Islamorada hosts up to 6 guests and provides proximity to the Lobster Trap Art Gift Shop and Gallery, situated nearly a 5-minute walk away. Providing guests with Wi-Fi and a private parking lot, the villa is a mere 1.1 km from the Hurricane Monument.
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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
Offering a year-round outdoor swimming pool, the 3-bedroom Island Time - Oceanview Balconies- Dock- Htd Pool Villa Islamorada is located 600 m from the Windley Key Fossil Reef Geological State Park and is ideal for up to 6 guests. The villa features opportunities for snorkelling and fishing in the area, 2.7 km from the History of Diving Museum.
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
Offering a year-round outdoor swimming pool, the 3-bedroom Island Time - Oceanview Balconies- Dock- Htd Pool Villa Islamorada is located 600 m from the Windley Key Fossil Reef Geological State Park and is ideal for up to 6 guests. The villa features opportunities for snorkelling and fishing in the area, 2.7 km from the History of Diving Museum.
Vacation Rental Florida Keys
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun loungers
Nestled in close proximity to Captain Hook s Marina Dive Center, Vacation Rental Florida Keys Marathon villa entices guests to explore various tourist destinations nearby.
Vacation Rental Florida Keys
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Sun loungers
Vacation Rental Florida Keys
Nestled in close proximity to Captain Hook s Marina Dive Center, Vacation Rental Florida Keys Marathon villa entices guests to explore various tourist destinations nearby.
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 within 25 minutes' walk of the Larry and Penny Thompson Park and allows guests to enjoy mini golf, billiards, and darts.
There are a Jacuzzi to enhance your stay.
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 within 25 minutes' walk of the Larry and Penny Thompson Park and allows guests to enjoy mini golf, billiards, and darts.
There are a Jacuzzi to enhance your stay.
New 3 Story In Homestead- 3/2.5 Balcony & Rooftop
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Situated 3.5 km from the outdoor sculptures "Coral Castle", the 3-bedroom New 3 Story In Homestead- 3/2.5 Balcony & Rooftop villa provides access to numerous tourist attractions in the area.
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
Situated 3.5 km from the outdoor sculptures "Coral Castle", the 3-bedroom New 3 Story In Homestead- 3/2.5 Balcony & Rooftop villa provides access to numerous tourist attractions in the area.
Blue Pearl New Waterfront Haven With Heated Pool ,70 Foot Dock, And More!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Golf centre
- Outdoor swimming pool
Located only 350 metres from the Florida Keys Aquarium Encounters, the 4-bedroom Blue Pearl New Waterfront Haven With Heated Pool ,70 Foot Dock, And More! Marathon villa offers opportunities for cycling and fishing in the area.
Blue Pearl New Waterfront Haven With Heated Pool ,70 Foot Dock, And More!
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Golf centre
- Outdoor swimming pool
Blue Pearl New Waterfront Haven With Heated Pool ,70 Foot Dock, And More!
Located only 350 metres from the Florida Keys Aquarium Encounters, the 4-bedroom Blue Pearl New Waterfront Haven With Heated Pool ,70 Foot Dock, And More! Marathon villa offers opportunities for cycling and fishing in the area.
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Guest favorite
Farmhouse Miami
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Saltwater pool
Offering a location 25 minutes' stroll from the Safari Edventure, Farmhouse Miami villa gives access to various tourist spots in the area. The 3-bedroom villa accommodates up to 10 guests and invites them to enjoy a terrace.
Farmhouse Miami
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Saltwater pool
Farmhouse Miami
Offering a location 25 minutes' stroll from the Safari Edventure, Farmhouse Miami villa gives access to various tourist spots in the area. The 3-bedroom villa accommodates up to 10 guests and invites them to enjoy a terrace.
The Tropical Paradise Villa
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Billiard tables
- Pool with view
Featuring a swimming pool, the 5-bedroom The Tropical Paradise Villa Miami is suitable for up to 12 people and is located about a 25-minute walk from the Larry and Penny Thompson Park. This 4-bathroom villa features opportunities for billiards in the area, 3.2 km from the zoological park "Zoo Miami".
The Tropical Paradise Villa
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Billiard tables
- Pool with view
The Tropical Paradise Villa
Featuring a swimming pool, the 5-bedroom The Tropical Paradise Villa Miami is suitable for up to 12 people and is located about a 25-minute walk from the Larry and Penny Thompson Park. This 4-bathroom villa features opportunities for billiards in the area, 3.2 km from the zoological park "Zoo Miami".
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Private beach
Seas The Keys Getaway
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Fitness centre
- Plunge pool
Situated in Duck Key, which is a census-designated place and unincorporated community in Monroe County, Florida, United States on an island of the same name in the middle Florida Keys, approximately a 25-minute walk from Little Conch Key Island, the 2-bedroom Seas The Keys Getaway Villa Duck Key comes with an outdoor swimming pool for guests to unwind. Suitable for up to 6 people, this villa provides a Jacuzzi, as well as snorkelling and fishing.
Seas The Keys Getaway
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Fitness centre
- Plunge pool
Seas The Keys Getaway
Situated in Duck Key, which is a census-designated place and unincorporated community in Monroe County, Florida, United States on an island of the same name in the middle Florida Keys, approximately a 25-minute walk from Little Conch Key Island, the 2-bedroom Seas The Keys Getaway Villa Duck Key comes with an outdoor swimming pool for guests to unwind. Suitable for up to 6 people, this villa provides a Jacuzzi, as well as snorkelling and fishing.
Villa Paradise Miami, Luxury Gem With Heated Pool, Game Room, Fire Pit, 3 Bed 2 Bath
- Cookware/ Kitchen utensils
- Flat-screen TV
- Mini-bar
- Ironing facilities
- Tea and coffee facilities
- Patio
Villa Paradise Miami, Luxury Gem With Heated Pool, Game Room, Fire Pit, 3 Bed 2 Bath is located 3.3 km from the Gold Coast Railroad Museum, giving access to various tourist spots nearby.
Villa Paradise Miami, Luxury Gem With Heated Pool, Game Room, Fire Pit, 3 Bed 2 Bath
- Cookware/ Kitchen utensils
- Flat-screen TV
- Mini-bar
- Ironing facilities
- Tea and coffee facilities
- Patio
Villa Paradise Miami, Luxury Gem With Heated Pool, Game Room, Fire Pit, 3 Bed 2 Bath
Villa Paradise Miami, Luxury Gem With Heated Pool, Game Room, Fire Pit, 3 Bed 2 Bath is located 3.3 km from the Gold Coast Railroad Museum, giving access to various tourist spots nearby.
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Private beach
Villas At Hawks Cay Resort
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Live entertainment
- Heated swimming pool
Staying at Villas At Hawks Cay Resort Duck Key, guests can visit the Calm Waters Spa, which is about a 5-minute walk away. Located in Duck Key, which is a census-designated place and unincorporated community in Monroe County, Florida, United States on an island of the same name in the middle Florida Keys, this property features a swimming pool, along with a Jacuzzi and a sauna.
This accommodation offers live performances for entertainment, as well as lawn tennis and cycling for sport lovers. Fitness lovers will appreciate yoga instruction.
Villas At Hawks Cay Resort
- Restaurant
- Free parking
- 24-hour reception
- Air conditioning
- Live entertainment
- Heated swimming pool
Villas At Hawks Cay Resort
Staying at Villas At Hawks Cay Resort Duck Key, guests can visit the Calm Waters Spa, which is about a 5-minute walk away. Located in Duck Key, which is a census-designated place and unincorporated community in Monroe County, Florida, United States on an island of the same name in the middle Florida Keys, this property features a swimming pool, along with a Jacuzzi and a sauna.
This accommodation offers live performances for entertainment, as well as lawn tennis and cycling for sport lovers. Fitness lovers will appreciate yoga instruction.
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$ |
More accommodations in Islamorada
Frequently Asked Questions
Which vacation rentals in Islamorada have ocean views?
Beachfront Villa at Islamorada and Isla Key Guava offer stunning ocean views. Enjoy your mornings with beautiful sunrises right from your balcony.
Book your stay in the spring for the best rates and views.
What vacation rentals in Islamorada are best for families?
Villas At Hawks Cay Resort and Anglers Reef Vacation Rental offer family-oriented amenities. These include spacious rooms and kid-friendly activities nearby.
Choose rentals with kitchens to prepare meals and save on dining for your family.
Are there dog-friendly vacation rentals in Islamorada?
Several options, like Seas The Keys Getaway, allow pets. Make sure to confirm pet policies before booking.
Check with local pet-friendly beaches for great outdoor fun with your dog.
Where can I find vacation rentals with pools in Islamorada?
Luxury Gem With Heated Pool and Blue Pearl New Waterfront Haven both feature private pools. Perfect for cooling off after a day in the sun.
Visit local restaurant patios that have happy hour specials for a nice break after swimming.
What are the best budget vacation rentals in Islamorada?
Vacation Rental Florida Keys and Villa Paradise Miami offer affordable stays. They provide comfortable accommodations without breaking the bank.
Travel in the off-peak season for the best deals and quieter surroundings.
Which vacation rentals in Islamorada are near beaches?
Beachfront Villa at Islamorada and Isla Key Mamey place you close to popular beaches. Enjoy sunbathing and swimming just steps from your rental.
Pack your beach essentials and arrive early for a good spot on busy weekends.
Are there vacation rentals with hot tubs in Islamorada?
The Tropical Paradise Villa features a hot tub, perfect for relaxation after a busy day. Enjoy the soothing water under the stars.
Be sure to book during weekdays for quieter private hot tub access.
What unique events occur in Islamorada?
Islamorada usually hosts the Florida Keys Stone Crab Festival in October. It's a great way to experience local culture and taste delicious seafood.
Attend on Saturday for live music and the freshest crab dishes.
How can I explore the best activities in Islamorada?
Check out local water sports, deep-sea fishing, and eco-tours. Many tours start near popular vacation rentals like Anglers Reef.
Book a guided tour early in the morning for the calmest waters and better wildlife spotting.
What are the must-visit places in Islamorada?
Don't miss the Theater of the Sea and the Rain Barrel Village for unique attractions. These spots are ideal for families and art lovers alike.
Plan visits during weekday mornings to avoid crowds at popular sites.
Islamorada and related destinations