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Here is a quick list of Vacation Rentals in Islamorada, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Pineapple Beach |
10.0 / 10 (1 Reviews) |
From 2875$ | |
| Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location |
8.0 / 10 (1 Reviews) |
From 1071$ | |
| Anglers Reef Paradise |
9.6 / 10 (19 Reviews) |
From 382$ | |
| Beachfront Villa At Islamorada By The Glamhomes |
1.0 / 10 (1 Reviews) |
From 2840$ | |
| Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable |
10.0 / 10 (2 Reviews) |
From 722$ |
Vacation rentals in Islamorada offer an exceptional opportunity for those seeking a serene getaway in the Florida Keys. This picturesque locale features a perfect blend of tropical charm and modern comforts, making it a top choice for travelers looking to escape the everyday hustle. From cozy beachfront cottages to luxurious waterfront villas, there's a diverse range of options suited for families, couples, and solo adventurers alike. Enjoy local attractions such as pristine beaches, fishing spots, and exquisite dining, all just a stone's throw from your rental. Planning a visit to Islamorada? Consider the endless possibilities that vacation rentals can provide for a memorable stay.
Best Islamorada Vacation Rentals
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Pineapple Beach
From 2875$
A 25-minute stroll from Pineapple Beach Villa takes guests to Windley Key, while the 45 - acre Founders Park is a 30-minute walk away. Extras include a microwave oven, a fridge, and kitchenware in a fully equipped kitchen and a bathtub, a separate toilet, and a shower in a bathroom.
You can get to Rain Barrel Sculpture Gallery in a few minutes by car.
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Gated Estate Duplex On The Bay With Dockage Apts
Gated Estate Duplex On The Bay With Dockage Apts Apartment is nearly 0.9 km from History of Diving Museum. This 2-bedroom venue also features a kitchen and 2 bathrooms.
The accommodation is located in Islamorada, a 5-minute walk from its centre. Hurricane Monument is just over 1.4 km away. Several restaurants such as Bitton Bistro Cafe and Subway are within 250 metres from Gated Estate Duplex On The Bay With Dockage Apts Apartment. Windley Key Fossil Reef Geological State Park is also a short ride away.
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Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location
From 1071$
This venue offers accommodation around a 5-minute ride from Upper Matecumbe Key Island, while Windley Key Island is 4.3 km away. The villa comprises 3 bedrooms and a fully equipped kitchen that provides guests with a fridge, an oven, and kitchenware.
Popular points of interest near the property include Lobster Trap Art Gift Shop and Gallery and Florida Keys History and Discovery Center. It takes 5 minutes on foot to reach Islamorada city centre. There are dining choices, such as Subway and Great Wall Taki Outi within 250 metres of the venue. You can get to History of Diving Museum in a few minutes by car.
Oceanfront Villas: Luxury Living in Islamorada
Oceanfront villas in Islamorada provide the ultimate luxurious experience, complete with stunning views of turquoise waters and golden sunsets. These spacious properties offer an array of amenities, including private pools, modern kitchens, and outdoor living spaces ideal for relaxation. Guests can enjoy direct beach access, making it easy to partake in various water activities such as snorkeling and paddleboarding. With ample room for families or groups of friends, these villas cater to those looking for a lavish getaway while remaining close to local restaurants and shops. Whether you're lounging by the pool or soaking in the hot tub, oceanfront villas set the stage for an unforgettable vacation.
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Beacon Reef 501
The 2-bedroom Beacon Reef 501 Villa is less than about 10 minutes' drive from Windley Key Island. A Jacuzzi are also offered on-site.
Popular points of interest near the venue include History of Diving Museum and Island Community Church. This beachfront villa is merely a 10-minute drive from Windley Key Fossil Reef Geological State Park. The centre of Islamorada is about 15 minutes' walk away. You can get to Upper Matecumbe Key Island in a few minutes by car.
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Anglers Reef Paradise
From 382$
Anglers Reef Paradise Villa is located close to Windley Key and offers a patio as well as a swimming pool. This venue is placed in a residential area, a few steps from Windley Key Fossil Reef Geological State Park.
The accommodation is a 15-minute drive to Indian Key State Historic Site and a 10-minute drive to the world-class museum "Florida Keys History and Discovery Center". The centre of Islamorada is 5 km away from the villa. There is a private beach in the neighbourhood. You can get to Rain Barrel Sculpture Gallery in a few minutes by car.
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Palms 407
The 2-bedroom Palms 407 Villa is less than 3.1 km from Upper Matecumbe Key Island. The venue features a Jacuzzi for you to relax.
The world-class museum "Florida Keys History and Discovery Center" is approximately 10 minutes' drive away. The city centre of Islamorada is 5 km away. You can get to Lobster Trap Art Gift Shop and Gallery in a few minutes by car.
Cozy Cottages: Charm Meets Comfort
Cozy cottages in Islamorada provide a charming alternative for those who prefer a more intimate setting. These quaint homes showcase the character of the keys while offering modern amenities to ensure a comfortable stay. Visitors can unwind in beautifully decorated interiors and enjoy easy access to sandy beaches and lush surroundings. Many cottages come equipped with kitchens and outdoor grills, making it simple to prepare fresh seafood caught locally. The warm and inviting atmosphere of these rentals makes them perfect for couples or small families seeking a peaceful escape in a secluded environment.
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Palms 317
Located in the beachfront, Palms 317 Villa boasts parking and Wi-Fi throughout the venue. Indian Key Historic State Park is settled at 3.1 km distance, while Lobster Trap Art Gift Shop and Gallery is 3.8 km from the accommodation.
The centre of Islamorada is nearly 5 km from the villa. You can get to Upper Matecumbe Key Island in a few minutes by car.
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Direct Oceanfront With Private Staircase To Beach Prestigious Islamorada Condocomplex Condo
The venue is fitted with a fully furnished kitchen that has facilities such as a microwave oven, a fridge, and kitchenware.
Upper Matecumbe Key Island can be reached by car in a couple of minutes, while Island Community Church is right by the accommodation. Indian Key State Historic Site is 3.4 km from this spacious apartment. Within a 6-minute walk guests can dine in Island Grill and Keys Grill. History of Diving Museum is located not far from the property.
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Gorgeous 2 Bedroom Condo With Panoramic Views Of The Atlantic Ocean, Condo
Located within a walking distance of History of Diving Museum and Island Community Church, this beachfront venue features views of the garden. A fully furnished kitchen is complete with a microwave oven, a refrigerator, and kitchenware.
The accommodation is settled 1.7 km from Lobster Trap Art Gift Shop and Gallery and 2.1km from Upper Matecumbe Key Island. The centre of Islamorada is only 2 km away. Guests can share a meal in Island Grill and Keys Grill, located about 500 metres away. Windley Key Island can be reached in a few minutes by car.
Family-Friendly Beach Houses: Fun for Everyone
Family-friendly beach houses are perfect for larger groups looking to spend quality time together in Islamorada. These spacious rentals often feature multiple bedrooms, large living areas, and expansive outdoor spaces, providing plenty of room for children and adults alike. With proximity to kid-friendly attractions and activities, families can easily plan fun-filled days filled with boating, kayaking, or relaxing on the beach. Many beach houses are equipped with game rooms, pools, and direct beach access, ensuring that everyone has something to enjoy. Create lasting memories in these welcoming homes, where the days are sunny, and a world of adventure awaits right at your doorstep.
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Escape To The Keys
Situated 3.5 km from Windley Key Fossil Reef Geological State Park, the spacious Escape To Keys Apartment offers accommodation in Islamorada. With access to Windley Key, this venue comes with 2 bedrooms and a fully equipped kitchen.
History of Diving Museum can be reached by car in a couple of minutes, while Islamorada is right by the property. Guests can walk to the 45 - acre Founders Park in 5 minutes. Escape To The Keys Apartment is set right next to private beaches.
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Sandglass 4
From 696$
Sandglass 4 Villa is situated nearly 25 minutes' walk from Anne's Beach in Islamorada and offers accommodation with a full kitchen. Wi-Fi is available throughout the venue too.
The 280-acre island "Lignumvitae Key Botanical State Park" is approximately 15 minutes' drive away. You can get to Indian Key Historic State Park in a few minutes by car.
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Entire Compound On Gated Bayfront Property Estate
Situated 1.2 km from Michelle Nicole Lowe Art Gallery, the beachfront Entire Compound On Gated Bayfront Property Estate Apartment offers accommodation in Islamorada. It also has a kitchen equipped with a refrigerator, an oven, and kitchenware.
The venue is located in Islamorada, a 5-minute walk from its centre. Lignumvitae Key Botanical State Park is within a 25-minute stroll away. It offers Bitton Bistro Cafe, which is sited 150 metres from the apartment and serves French cuisine. Upper Matecumbe Key Island is also a short ride away.
Pet-Friendly Rentals: Bring Your Four-Legged Friends
Pet-friendly rentals in Islamorada allow you to bring your beloved pets along for your tropical vacation. These thoughtfully designed properties feature enclosed yards and easy access to pet-friendly beaches, ensuring your furry companions enjoy their time as much as you do. Many pet-friendly options come equipped with dog beds, feeding stations, and plenty of space for your pets to roam. Enjoy exploring the scenic trails and parks that allow pets while making precious memories with your four-legged friends. Finding the right rental can make it possible to experience the beauty of Islamorada without leaving anyone behind.
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Heart Of Morada
At Heart Of Morada Villa you'll be within just a 5-minute stroll of Upper Matecumbe Key Island and close to Keys History & Discovery Center. It is composed of 3 bedrooms alongside with a kitchen and 4 bathrooms.
Local attractions include Hurricane Monument steps away from the venue and city centre 1 km away. Indian Key State Historic Site is 19 minutes' walk from this accommodation. You can taste French cuisine in Cafe Moka Islamorada, located 5 minutes' stroll from Heart Of Morada Villa. You can get to History of Diving Museum in a few minutes by car.
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Beachfront Villa At Islamorada By The Glamhomes
From 2840$
Offering 4 bedrooms, Beachfront Villa At Islamorada By The Glamhomes with a swimming pool is fitted with a deck overlooking the sea. Indian Key Historic State Park is a 10-minute drive away from the venue.
Featuring an own beach, the property is about just 200 metres from Lower Matecumbe Key Island.
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Palms 417
Palms 417 Villa is a beachfront venue located about at a distance of 3.1 km from Upper Matecumbe Key Island. It also has 1 bedroom as well as a fully-fitted kitchen which is equipped with a microwave oven, a refrigerator, and kitchenware.
The centre of Islamorada is nearly 5 km from the accommodation. Lobster Trap Art Gift Shop and Gallery can be reached in 10 minutes by car. You can get to Hurricane Monument in a few minutes by car.
Waterfront Condos: Scenic Views and Easy Access
Waterfront condos in Islamorada provide an excellent option for those who want a modern, chic living space with stunning views of the ocean. These properties typically include convenient amenities such as pools, fitness centers, and community lounges, catering to guests looking for a resort-like atmosphere. With local attractions just a short distance away, visitors can easily explore the vibrant culture while enjoying peaceful evenings on their private balconies. Ideal for couples or solo travelers, these condos promise a hassle-free experience with easy access to ocean activities like fishing and boating just steps away from your door.
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This Condo Is Located In One Of Islamorada'S Most Prestigious Condo Complexes, Condo
A fully-fitted kitchen is also available, as well as a fridge, an oven, and kitchenware.
The venue is set within a 15-minute walk of the centre of Islamorada and 5 minutes’ drive to Anne s Beach. It is located 3.4 km from Lignumvitae Key Botanical State Park, very close to History of Diving Museum. Within 500 metres from the accommodation, Island Grill and Keys Grill serve a wide selection of dishes. Lobster Trap Art Gift Shop and Gallery is also a short ride away.
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1 Bedroom Unit With A Nice View Of The Florida Bay, Condo
Offering a heated pool, 1 Bedroom Unit With A Nice View Of The Florida Bay, Condo apartment is set 3.8 km from Lobster Trap Art Gift Shop and Gallery. Upper Matecumbe Key Island is 3.1 km from this venue.
The property is set 5 km from the center of Islamorada. Hurricane Monument is a short taxi ride away.
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3 Lux Ensuites Walk Boat Island
From 705$
3 Lux Ensuites Walk Boat Island is located within merely 0.8 km from In the Doghouse Art Studio and a 25-minute walk away from History of Diving Museum. The venue also comes with a full kitchen, which is equipped with a fridge, an oven, and kitchenware.
The villa is 2 km from the centre of Islamorada and in vicinity of Hurricane Monument. This property is also set close to Pasta Pantaleo Signature Gallery. Kaiyo Grill & Sushi Bar offers a range of Japanese meals and is located 100 metres away. You can get to Indian Key State Historic Site in a few minutes by car.
Secluded Retreats: Peaceful Getaways
For those seeking tranquility, secluded retreats in Islamorada are the perfect escape from the hustle and bustle of everyday life. These rentals often boast lush landscapes and private gardens, allowing guests to relax in a serene environment. Many secluded properties are located away from public beaches, providing a more intimate experience with natural surroundings. Enjoy activities like birdwatching, meditation, or simply lounging in a hammock under palm trees. Whether you’re looking for solitude or a romantic getaway, secluded retreats offer an idyllic setting for rejuvenation.
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75130 Overseas Highway
75130 Overseas Highway Villa is situated approximately 10 minutes' drive from Craig Key Island in Islamorada and offers accommodation with a fully equipped kitchen. This villa has 2 bedrooms and 2 bathrooms.
The 280-acre island "Lignumvitae Key Botanical State Park" is approximately 10 minutes' drive away. You can get to Anne's Beach in a few minutes by car.
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Peaceful Palms A2
Peaceful Palms A2 Villa is set 2.6 km from History of Diving Museum and represents a 3-bedroom venue with a terrace. Guests, staying at this accommodation, can use a fully equipped kitchen with a microwave oven, a fridge, and kitchenware to prepare home-cooked meals.
Rain Barrel Village is approximately 10 minutes' drive away. The centre of Islamorada is 4 km away. Such major Islamorada sights including Windley Key Fossil Reef Geological State Park are also located nearby. You can get to Rain Barrel Sculpture Gallery in a few minutes by car.
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Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
From 722$
The venue is merely 1.2 km from Upper Matecumbe Key Island and 500 metres from the class museum "Florida Keys History and Discovery Center". The accommodation also comes with a fully-fitted kitchen, which is equipped with a microwave, a fridge, and kitchenware.
The villa is located 5 minutes’ walk from the centre of Islamorada. Such major Islamorada sights including Lobster Trap Art Gift Shop and Gallery are also located nearby. Subway is a fast food restaurant serving American dishes. You can get to Indian Key State Historic Site in a few minutes by car.
Luxury Townhomes: Spacious Living in Paradise
Luxury townhomes in Islamorada cater to those who prefer sophisticated spaces in a coastal paradise. These upscale accommodations often feature open layouts, gourmet kitchens, and private balconies with breathtaking views of the water. With amenities like golf carts, private pools, and direct marina access, guests can enjoy the best of both luxury and leisure. Townhomes are often strategically located close to local attractions, restaurants, and shops, ensuring easy access to everything Islamorada has to offer. Perfect for family vacations or group retreats, these stylish properties provide both comfort and elegance during your stay.
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Lyons Landing
Lyons Landing Villa is located 20 minutes' walk from Windley Key Island and 25 minutes' walk away from Windley Key Fossil Reef Geological State Park. There is a fully equipped kitchen with a microwave, a refrigerator, and kitchenware while 3 bathrooms are included as well.
You can get to History of Diving Museum in a few minutes by car.
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Anglers Reef Vacation Rental
From 365$
Anglers Reef Vacation Rental is situated around a 15-minute ride from Upper Matecumbe Key Island in Islamorada and offers accommodation with a fully equipped kitchen. This establishment also has 2 bedrooms and a heated swimming pool.
Popular points of interest near the venue include Windley Key Fossil Reef Geological State Park and Windley Key. Lobster Trap Art Gift Shop and Gallery is nestled 4.6 km from the villa. The property is 5 km from the centre of Islamorada. You can get to Rain Barrel Village in a few minutes by car.
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Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
From 1360$
The venue is only around 1 km from Michelle Nicole Lowe Art Gallery and about 2.1 km away from Lignumvitae Key Botanical State Park. This accommodation has a fully-fitted kitchen provided with amenities, such as a microwave oven, a fridge, and kitchenware for self-catering.
Popular points of interest near the villa include Lobster Trap Art Gift Shop and Gallery and the world-class museum "Florida Keys History and Discovery Center". It takes a 5 minutes' walk to get to Islamorada city centre. Guests may find the quick bites Burger King within 450 metres from the property. You can get to Windley Key Fossil Reef Geological State Park in a few minutes by car.
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Islamorada Modern Penthouse With Private Beach
Islamorada Modern Penthouse With Private Beach Villa is situated within 25 minutes' walk of Lobster Trap Art Gift Shop and Gallery in Islamorada and offers accommodation with a fully-fitted kitchen. Guests enjoy a Jacuzzi as well as an outdoor pool area on site.
The venue is 3 km from the centre of Islamorada and in vicinity of Indian Key State Historic Site. At this villa you'll be within a 5-minute stroll of FNX Club by Islamorada Fitness. American dishes can be enjoyed in Square Grouper Islamorada, which is 300 metres away. You can get to Upper Matecumbe Key Island in a few minutes by car.
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Beautiful Condo With Panoramic Views Of The Atlantic Ocean, Condo
Situated 3.1 km from Upper Matecumbe Key Island, Beautiful Condo With Panoramic Views Of The Atlantic Ocean, Condo apartment provides accommodation with Wi-Fi throughout the venue. A fridge, an oven, and kitchenware are provided in a fully equipped kitchen of the property.
The world-class museum "Florida Keys History and Discovery Center" is located 3.7 km from the venue. The centre of Islamorada is around 5 km away. Lobster Trap Art Gift Shop and Gallery is also a short ride away.