Skip to main content

The 10 Best Vacation Rentals in Islamorada, USA

Check out our selection of great vacation rentals in Islamorada

Filter by:


Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

The villa with a terrace and pool views features 2 bedrooms, 2 living rooms, a flat-screen TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the villa. The property has an outdoor dining area.

loved the location and the quick responses from the host.

Show more Show less
9
Wonderful
24 reviews

This air-conditioned holiday home has 2 bedrooms and 2.5 bathrooms, a cable flat-screen TV, and a fully equipped kitchen. The holiday home also provides a bathroom with a shower.

The holiday home includes a barbecue. There is a a terrace at this property and guests can go snorkelling, fishing and diving nearby. Two kayaks and 2 bicycles are offered. A boat hire is available for a surcharge.

It was very clean and confortable; and the facilities where great, we enjoyed our time at the beach and used the canoes and paddle board! Great time

Show more Show less
9.2
Wonderful
26 reviews

Situated 1.9 km from Sea Oats Beach, Matecumbe Resort offers 2-star accommodation in Islamorada and has a private beach area, an outdoor swimming pool and a garden. This beachfront property offers access to table tennis, free private parking and free WiFi. The property offers allergy-free units and is located 9.2 km from Upper Matecumbe Key.

Beautiful property and room was gorgeous and clean and bed was so comfy. Staff were as so friendly and accommodating.

Show more Show less
8.5
Very Good
322 reviews
Price from
$165
per night

Situated in Islamorada and only 3.8 km from Windley Key, EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS features accommodation with sea views, free WiFi and free private parking. This holiday home offers a private beach area, a garden, as well as a tennis court. The property features a year-round outdoor pool with a pool bar and is set 9.1 km from Upper Matecumbe Key.

Show more Show less
8.5
Very Good
2 reviews
Price from
$135.55
per night

The spacious holiday home with a balcony and sea views features 2 bedrooms, a living room, a TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area.

Show more Show less
Price from
$185.36
per night

Set in Islamorada, 1.1 km from Sea Oats Beach and 10 km from Upper Matecumbe Key, Beachfront Villa at Islamorada BY THE GLAMHOMES offers a private beach area and air conditioning. This beachfront property offers access to a balcony, free private parking and free WiFi. On clear days, guests can head outside to enjoy the villa's outdoor fireplace or simply kick back and relax.

Show more Show less
Price from
$1,530
per night

Set in Islamorada, 1.2 km from Sea Oats Beach and 2.2 km from Anne's Beach, Plaza Del Sol offers air-conditioned accommodation with a terrace and free WiFi. This holiday home features accommodation with a balcony. The property is non-smoking and is situated 13 km from Upper Matecumbe Key.

Show more Show less
Price from
$267.11
per night

The holiday home features 2 bedrooms, a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area.

Show more Show less

The spacious holiday home has 6 bedrooms, 6 bathrooms, bed linen, towels, a TV with cable channels, a dining area, a fully equipped kitchen, and a balcony with sea views. Guests can take in the ambience of the surroundings from an outdoor dining area or keep themselves warm by the fireplace on colder days. For added privacy, the accommodation features a private entrance.

Show more Show less
Price from
$1,035.64
per night

The spacious holiday home features 6 bedrooms, a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 5 bathrooms with a walk-in shower. Towels and bed linen are provided in the holiday home. The property has an outdoor dining area.

Show more Show less

Most booked vacation rentals in Islamorada this month

Enjoy breakfast in Islamorada!

  • Anglers Reef Getaway
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 24 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
    9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 26 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.

    perfektes Südstaatenfeeling sehr exquisit und sicher

  • Matecumbe Resort
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 322 reviews

    Matecumbe Resort features a public bath and air-conditioned accommodations in Islamorada, 1.2 miles from Sea Oats Beach.

    El lugar es súper bonito! Y es Perfecto para la familia

  • Tollgate Tides
    Breakfast options

    Just a 6-minute walk from Anne's Beach and one mile from Sea Oats Beach, Tollgate Tides features accommodations in Islamorada with a garden.

  • Beachfront Villa at Islamorada BY THE GLAMHOMES

    Providing an outdoor swimming pool, Beachfront Villa at Islamorada BY THE GLAMHOMES offers accommodations in Islamorada.

  • Plaza Del Sol
    Breakfast options

    Plaza Del Sol is located in Islamorada, just 1.4 miles from Anne's Beach and 8.2 miles from Upper Matecumbe Key. This vacation home features accommodations with a balcony.

  • Two White Turtles

    Two White Turtles offers accommodations in Islamorada, 21 miles from Florida Keys Aquarium Encounters and 21 miles from Pigeon Key.

  • Waterfront Wonder

    Waterfront Wonder is located in Islamorada, just 1.5 miles from Anne's Beach and 7.6 miles from Upper Matecumbe Key. Guests may go for a swim in the private pool.

These vacation rentals in Islamorada have options with FREE cancellation

  • Casa Koto
    Free cancellation options available

    Casa Koto offers accommodations in Islamorada, a 13-minute walk from Sea Oats Beach and 1.4 miles from Anne's Beach. This beachfront property offers access to a balcony and free Wifi.

  • Sun-kissed Bliss
    Free cancellation options available

    Sun-kissed Bliss offers accommodations in Islamorada, a few steps from Sea Oats Beach and a 19-minute walk from Anne's Beach.

  • EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS
    8.5
    Scored 8.5
    Very Good
    Rated 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.

  • Paradise Beach
    Free cancellation options available

    Paradise Beach offers accommodations in Islamorada, a few steps from Sea Oats Beach and 1.2 miles from Anne's Beach. This beachfront property offers access to free Wifi.

FAQ about vacation rentals in Islamorada




Vacation Rentals That Guests Love in Islamorada

  • Avg. price/night: $684.23
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 247 reviews
    The villas were spacious and clean
    W
    William
    Family with young children
  • Avg. price/night: $381.38
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 814 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: $236.45
    7.0
    Scored 7.0
    Good
    Rated good
     · 1,239 reviews
    Our 2 storey pool villa was fabulous. Really liked the pool area and breakfast was nice in the lobby.
    Sarah
    Young couple
  • Avg. price/night: $381.38
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 814 reviews
    Upgraded to a villa! Beautiful spot to watch sunrise. Hot tub and two pools were lovely. Champagne complimentary on arrival. Very good restaurant next door. Good variety of foods at breakfast which you could eat at outdoor tables or take to your room. Villa very clean with a well equipped kitchen. All staff we encountered were very pleasant!
    Mason
    Young couple
  • 9.2
    Scored 9.2
    Wonderful
    Rated wonderful
     · 26 reviews
    The villa was well located and well appointed. From beach towels to kitchen appliances, from dishes to kayaks and bikes, this place seemed designed with our comfort and relaxation in mind.
    Anne
    Young couple
  • Avg. price/night: $209.42
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,038 reviews
    Brandon did a terrific job checking us in. When he found out one of us was blind he changed us from upstairs to a villa! Told us about all the amenities and even suggested a fishing guide. Great job! View was fantastic also!!!)
    Debbi
    Group
  • Avg. price/night: $684.23
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 247 reviews
    The villas are so confortable and have all the amenities that we need
    Martina
    Group
  • Avg. price/night: $381.38
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 814 reviews
    My husband picked this resort to spend his birthday. The pictures looked lovely but surely don't do it justice. It was beautiful. We rented a 2 bedroom villa with a full kitchen. Even our children were in love with the place. The beach and 2 pools were just a few feet from the villa which was perfect and the staff was lovely and helpful and so professional. I am definitely coming back!
    Jennifer
    Family with young children
  • Avg. price/night: $684.23
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 247 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: $209.42
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,038 reviews
    Was supposed to have entire villa with a patio. Got a single room with no patio.
    Sonja
    Young couple