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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.
Search villas in Islamorada

Most booked villas in Islamorada this month

Enjoy breakfast in Islamorada!

  • Anglers Reef Getaway
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 23 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.

    The amenities,the location, the villas and the pool

  • Anglers Reef Paradise
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 22 reviews

    Anglers Reef Paradise is located in Islamorada, 984 feet from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi.

    Location & the grounds & pool were amazing.

  • La Dolce Vita Villa

    La Dolce Vita Villa offers accommodations in Islamorada, 1.4 miles from Windley Key and 4.7 miles from Upper Matecumbe Key. This property offers access to a balcony and free private parking.

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

    Isla Honeydew - 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.

  • Pineapple Beach
    Breakfast options

    Pineapple Beach offers accommodations in Islamorada, 6.7 miles from Upper Matecumbe Key and 7 miles from Pigeon Key. The air-conditioned accommodation is 3.4 miles from Windley Key.

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

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

  • Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!

    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.

  • 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.

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

  • Anglers Reef Vacation Rental
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    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.

  • 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 Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location

    Isla Key Lychee - 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 is located in Islamorada, just a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

  • 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.

  • 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

    Just a 4-minute walk from History of Diving Museum and 1.2 miles from Windley Key Fossil Reef Geological State Park, Beacon Reef 222 features accommodations in Islamorada with a garden.

  • 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.

  • Peaceful Palms A2

    Peaceful Palms A2 is a recently renovated vacation home in Islamorada, near Windley Key. This vacation home features air-conditioned accommodations with a terrace.

  • Palms 417
    Central location

    Palms 417 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key. This beachfront property offers access to a terrace.

  • Palms 407
    Central location

    Palms 407 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 404
    Central location

    Palms 404 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 317
    Central location

    Palms 317 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 313
    Central location

    Palms 313 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 301
    Central location

    Palms 301 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

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

  • West Plaza Del Lago

    West Plaza Del Lago offers accommodations in Islamorada, a 12-minute walk from Sea Oats Beach and 1.3 miles from Anne's Beach.

  • Villa Riolo

    Villa Riolo is located in Islamorada, just 1.6 miles from Sea Oats Beach and 5.7 miles from Upper Matecumbe Key. Both free Wifi and parking on-site are available at the vacation home free of charge.

  • Sandglass 4

    Sandglass 4 is located in Islamorada, just a few steps from Sea Oats Beach and 1.4 miles from Anne's Beach.

  • Pelican Landing

    Pelican Landing is located in Islamorada, just a 12-minute walk from Sea Oats Beach and 1.4 miles from Anne's Beach.

  • Palms 309

    Palms 309 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Lyons Landing

    Lyons Landing offers accommodations in Islamorada, 1.6 miles from Windley Key and 4.8 miles from Upper Matecumbe Key.

  • Harbor House

    Harbor House is located in Islamorada, just 1.4 miles from Windley Key and 4.7 miles from Upper Matecumbe Key.

  • Blue Water Retreat

    Blue Water Retreat offers accommodations in Islamorada, 1.3 miles from Sea Oats Beach and 5.9 miles from Upper Matecumbe Key. This beachfront property offers access to a balcony.

Villas That Guests Love in Islamorada

  • Avg. price/night: $504.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 245 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: $504.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 245 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: $504.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 245 reviews
    The villas were spacious and clean
    W
    William
    Family with young children
  • Avg. price/night: $280.13
    Scored 8.1
    8.1
    Rated very good
    Very Good
     · 848 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: $504.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 245 reviews
    The villas are so confortable and have all the amenities that we need
    Martina
    Group
  • Avg. price/night: $504.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 245 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: $504.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 245 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: $252
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 881 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: $280.12
    Scored 7.8
    7.8
    Rated good
    Good
     · 1,047 reviews
    Beachfront villa, beautiful location. Friendly staff
    G
    Glenn
    Family with young children
  • Avg. price/night: $504.23
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 245 reviews
    The villas were a great size to ensure a comfortable stay and well equipped in the kitchen. Having boat slips on property was a great Convenience. The property was beautiful and staff were very friendly.
    Jessica
    Family with young children