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The best villas in Islamorada

Check out our selection of great villas in Islamorada

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Anglers Reef Getaway, hotel in Islamorada

Offering an outdoor swimming pool and a garden, Anglers Reef Getaway in Islamorada is close to Windley Key and Windley Key Fossil Reef Geological State Park.

The area and amenities are great.
Scored 9.4
9.4
Rated wonderful
Wonderful
17 reviews
Anglers Reef Paradise, hotel in Islamorada

Just a 6-minute walk from Windley Key and one mile from Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise features accommodations in Islamorada, with pool with a view and a garden.

Beautiful house, location and community! Highly recommend!
Scored 9.5
9.5
Rated exceptional
Exceptional
23 reviews
Hideaway with Resort Privileges, hotel in Key Largo

Hideaway with Resort Privileges offers accommodations in Key Largo, 3.2 miles from Pigeon Key and 5.2 miles from John Pennekamp State Park.

Spotlessly clean, great location, and every amenity you can think of. Just perfect!
Scored 9.3
9.3
Rated wonderful
Wonderful
19 reviews
LICENSED MGR - LUXURIOUS OCEANFRONT CONDO W/STUNNING VIEWS - UPSCALE OCEANFRONT RESORT!, hotel in Key Largo

Featuring a garden, LICENSED MGR - LUXURIOUS OCEANFRONT CONDO W/STUNNING VIEWS - UPSCALE OCEANFRONT RESORT! provides accommodations in Key Largo.

fantastic view , great location
Scored 9.2
9.2
Rated wonderful
Wonderful
5 reviews
LICENSED Mgr - LUXURY VIP PENTHOUSE SUITE - OFFERS RESORTS BEST PANORAMIC OCEAN VIEWS!, hotel in Key Largo

LICENSED Mgr - LUXURY VIP PENTHOUSE SUITE - OFFERS RESORTS BEST PANORAMIC OCEAN VIEWS! is located in Key Largo, just 3.3 miles from Pigeon Key and 5.5 miles from John Pennekamp State Park.

Amazing views, fully functional kitchen and onsite security. The large pool was extra nice.
Scored 9.4
9.4
Rated wonderful
Wonderful
5 reviews
LICENSED MGR - 3/3.5 MODERN VILLA - KEY LARGO'S PREMIER OCEANFRONT RESORT AND MARINA!, hotel in Key Largo

LICENSED MGR - 3/3.5 MODERN VILLA - KEY LARGO'S PREMIER OCEANFRONT RESORT AND MARINA! offers accommodations in Key Largo, 3.3 miles from Pigeon Key and 5.5 miles from John Pennekamp State Park.

Unit was beautiful. 3 stories, comfortable. No complaints about the owners unit. It was good and he is a conscientious owner. Great beds. Overall the villa property was nice.
Scored 8.4
8.4
Rated very good
Very Good
5 reviews
All villas in Islamorada
Looking for a villa?
Perfect for families, groups, or couples who enjoy luxury and independence while traveling. Enjoy the space and privacy of these fully-furnished, free-standing mansions – travelers can cook, lounge, and explore at their own pace. Note that in Bali, a resort will also be called a villa.

Most booked villas in Islamorada this month

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Enjoy breakfast in Islamorada!

  • Anglers Reef Getaway
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 17 reviews

    Offering an outdoor swimming pool and a garden, Anglers Reef Getaway in Islamorada is close to Windley Key and Windley Key Fossil Reef Geological State Park.

    loved the location and the quick responses from the host.

  • Anglers Reef Paradise
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 23 reviews

    Just a 6-minute walk from Windley Key and one mile from Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise features accommodations in Islamorada, with pool with a view and a garden.

    Location & the grounds & pool were amazing.

  • At The Sandbar - Oceanfront, Htd Pool, Dock, GameRoom

    At The Sandbar - Oceanfront, Htd Pool, Dock, GameRoom is located in Islamorada, just a 10-minute walk from Windley Key and 3.1 miles from Upper Matecumbe Key.

  • Castaway Island Vacation Bungalow

    Castaway Island Vacation Bungalow offers accommodations in Islamorada, 1.6 miles from Sea Oats Beach and 5.2 miles from Upper Matecumbe Key.

  • Exceptional VENETIAN SHORES home with pool, dock and boat lift, home

    Exceptional VENETIAN SHORES home with pool, dock and boat lift, home is located in Islamorada, just 1.6 miles from Windley Key and 4.8 miles from Upper Matecumbe Key.

  • Treasure Cove
    Breakfast options

    Treasure Cove is located in Islamorada, just a 1-minute walk from Sea Oats Beach and 1.3 miles from Anne's Beach.

  • Treasure Harbor Hideaway - Upper

    Treasure Harbor Hideaway - Upper is located in Islamorada, just 1.7 miles from Windley Key and 5 miles from Upper Matecumbe Key.

  • Treasure Harbor Hideaway - Lower

    Treasure Harbor Hideaway - Lower is located in Islamorada, just 5 miles from Upper Matecumbe Key and 8.5 miles from Pigeon Key. Guests can go for a swim in the pool with a view.

Great access to the city center! Check these villas in Islamorada

  • Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views! is located in Islamorada, just a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

  • Anglers Reef Vacation Rental
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 2 reviews

    Just a 5-minute walk from Windley Key and one mile from Windley Key Fossil Reef Geological State Park, Anglers Reef Vacation Rental features accommodations in Islamorada with barbecue facilities.

  • Key Lime Cottage in the heart of Islamorada
    Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 3 reviews

    Key Lime Cottage in the heart of Islamorada offers accommodations in Islamorada, 1.6 miles from Sea Oats Beach and 5.3 miles from Upper Matecumbe Key.

    Nos encantó el cottage. Very cozy! La anfitriona super nice and sweet. Pendiente de mis mensajes todo el tiempo y asegurándose de que estuviéramos cómodos.

  • EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 2 reviews

    EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS in Islamorada provides accommodations with a private beach area, an outdoor swimming pool, and a garden.

  • Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

    Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

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

    Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

  • Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable

    Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

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

    Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

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

    Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

  • Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location

    Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

  • Lush tropical plantings in a gated compound located directly on the Florida Bay cottage

    Lush tropical plantings in a gated compound located directly on the Florida Bay cottage is located in Islamorada, just 13 miles from Pigeon Key and 21 miles from John Pennekamp State Park.

  • Little Bay Cottage

    Little Bay Cottage offers accommodations in Islamorada, 2.7 miles from Windley Key and 13 miles from Pigeon Key. The air-conditioned accommodation is a 13-minute walk from Upper Matecumbe Key.

  • Little Bay Compound

    Just a 13-minute walk from Upper Matecumbe Key and 0.6 miles from History of Diving Museum, Little Bay Compound features accommodations in Islamorada with a garden.

  • 2 houses located on a private peninsula, home

    2 houses located on a private peninsula, home offers accommodations in Islamorada, 3 miles from Windley Key and 13 miles from Pigeon Key.

  • Martin Family Fish Camp

    Martin Family Fish Camp offers accommodations in Islamorada, a 7-minute walk from Upper Matecumbe Key and 3 miles from Windley Key.

  • The Oasis
    Central location

    Just a 18-minute walk from Upper Matecumbe Key and half a mile from History of Diving Museum, The Oasis features accommodations in Islamorada with a garden.

  • 3 Lux Ensuites Walk Boat Island

    3 Lux Ensuites Walk Boat Island offers accommodations in Islamorada, a 5-minute walk from Upper Matecumbe Key and 3.4 miles from Windley Key.

  • Beacon Reef 503

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 503 features accommodations in Islamorada with a garden.

  • Beacon Reef 501

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 501 features accommodations in Islamorada with a garden.

  • Beacon Reef 406

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 406 features accommodations in Islamorada with a garden.

  • Beacon Reef 310

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 310 features accommodations in Islamorada with a garden.

  • Beacon Reef 307

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 307 features accommodations in Islamorada with a garden.

  • Beacon Reef 306

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 306 features accommodations in Islamorada with a garden.

  • Beacon Reef 301

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 301 features accommodations in Islamorada with a garden.

  • Beacon Reef 222

    Beacon Reef 222 offers accommodations in Islamorada, 1.5 miles from Upper Matecumbe Key and 1.9 miles from Windley Key. With sea views, this accommodation features a terrace and a swimming pool.

  • Waterfront Home With Beautiful VIews home

    Waterfront Home With Beautiful VIews home is located in Islamorada, just 11 miles from Pigeon Key and 19 miles from John Pennekamp State Park.

  • Sunshine Place
    Central location

    Sunshine Place offers accommodations in Islamorada, a 17-minute walk from Windley Key and 2.6 miles from Upper Matecumbe Key.

  • Islamorada home, ocean views, playroom, near Tiki Bar, pool, and boat dockage, ultimate Keys getaway home

    Islamorada home, ocean views, playroom, near Tiki Bar, pool, and boat dockage, ultimate Keys getaway home is located in Islamorada, just a 10-minute walk from Windley Key and 3.1 miles from Upper...

Traveling by car? These villas in Islamorada offer free parking!

Villas That Guests Love in Islamorada

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  • Avg. price/night: $360.20
    Scored 7.8
    7.8
    Rated good
    Good
     · 1,067 reviews
    I loved the property I come out here every year and it never disappoints! The pool villas are my favorite to stay at
    leon
    Young couple
  • Avg. price/night: $540.43
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 251 reviews
    We had a great time at Bayside Villas. The townhome was clean and comfortable. The pool and boat slips were close and convenient. We really enjoyed having access to the resort. We enjoyed the pool, poolside restaurant and all the amenities there. We also loved being able to contact the shuttle for rides to and from the resort and local restaurants. We thoroughly enjoyed our stay and look forward to visiting again later this summer.
    Michael
    Family with young children
  • Avg. price/night: $540.43
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 251 reviews
    The location of the property. Close to great restaurants. The basketball by the beach was phenomenal, ping pong and activities were great. The pools were great and the view of sunset by the villas pool was fantastic.Beautiful property. We will return.
    Maurizio
    Family with young children
  • Avg. price/night: $540.43
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 251 reviews
    The villas were spacious and clean
    W
    William
    Family with young children
  • Avg. price/night: $460.13
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 920 reviews
    The layout and I like that’s acomplete boutique hotel unique great staff and absolutely great planned villas n rooms
    ventura
    Family with young children
  • Avg. price/night: $540.43
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 251 reviews
    The villas are so confortable and have all the amenities that we need
    Martina
    Group
  • Avg. price/night: $540.43
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 251 reviews
    The villas are nice enough, clean and comfortable. The pool area is absolutely phenomenal, particularly at sunset.
    A
    Anonymous
    Family with young children
  • Avg. price/night: $540.43
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 251 reviews
    The best thing about this villa was the ability to use the Islander Resort for a fraction of the price. I was a little disappointed in the quality of the Villa although it was cheaper than its sister property it was still pricey. The outside of the villas are beautiful but they definitely could use some updated paint and carpeting inside. If you are looking for value in comparison to the Islander then this is the perfect spot. Overall I still really enjoyed the stay. Very close to restaurants.
    Sarah
    Family with young children
  • Avg. price/night: $391.50
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 849 reviews
    The villas were very comfortable and clean, the grounds were well kept and the property is excellent for a quite and peaceful vacation!
    Daniel
    Young couple
  • Avg. price/night: $391.51
    Scored 7.7
    7.7
    Rated good
    Good
     · 1,063 reviews
    Beachfront villa, beautiful location. Friendly staff
    G
    Glenn
    Family with young children