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The Islands of Islamorada

Property class: 4

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Photo gallery for The Islands of Islamorada

A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.
A gated entrance to a resort with palm trees and a clear sky.
A pool area with clear blue water, white lounge chairs, and palm trees.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Hot tub
  • Spa
  • Parking included
  • Free WiFi
  • Air conditioning
The current price is $467
$416 nightly
$467 total
Total with taxes and fees
Sep 23 - Sep 24

Explore the area

View in a map
82779 Old Hwy, Islamorada, FL, 33036
  • Place, History of Diving Museum
    ‪8 min walk‬
  • Place, Islamorada Brewery & Distillery
    ‪9 min walk‬
  • Place, beach near Islamorada
    ‪14 min walk‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪47 min drive‬

Room options

View all photos for Villa, Oceanfront (Oceanfront Villa)

Villa, Oceanfront (Oceanfront Villa) | Premium bedding, pillowtop beds, in-room safe, blackout drapes

Villa, Oceanfront (Oceanfront Villa)

  • Ocean view
  • 3100 sq ft
  • 4 bedrooms
  • Sleeps 8
  • 3 King Beds and 2 Twin Beds
  • Free WiFi

View all photos for Villa, Accessible, Ocean View (Ocean View Villa - Accessible)

Premium bedding, pillowtop beds, in-room safe, blackout drapes

Villa, Accessible, Ocean View (Ocean View Villa - Accessible)

  • Ocean view
  • 3100 sq ft
  • 4 bedrooms
  • Sleeps 8
  • 2 Twin Beds and 3 King Beds
  • Free WiFi

View all photos for Family Villa, Ocean View (Ocean View Family Villa)

Family Villa, Ocean View (Ocean View Family Villa) | Living room | Smart TV, Netflix, Hulu, streaming services

Family Villa, Ocean View (Ocean View Family Villa)

  • Ocean view
  • 3100 sq ft
  • 4 bedrooms
  • Sleeps 10
  • 3 King Beds and 2 Twin Bunk Beds
  • Free WiFi

View all photos for Suite, 1 King Bed with Sofa bed, Ocean View (Oceanview King Suite)

Suite, 1 King Bed with Sofa bed, Ocean View (Oceanview King Suite) | Balcony

Suite, 1 King Bed with Sofa bed, Ocean View (Oceanview King Suite)

  • Ocean view
  • 656 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Queen Sofa Bed
  • Free WiFi

View all photos for Villa, Ocean View (Ocean View Villa)

Premium bedding, pillowtop beds, in-room safe, blackout drapes

Villa, Ocean View (Ocean View Villa)

10.0 out of 10
Exceptional
(1 review)
  • Ocean view
  • 3098 sq ft
  • 4 bedrooms
  • Sleeps 8
  • 3 King Beds and 2 Twin Beds
  • Free WiFi

View all photos for Suite, 1 King Bed with Sofa bed, Accessible, Ocean View (Oceanview King Suite - Accessible)

Suite, 1 King Bed with Sofa bed, Accessible, Ocean View (Oceanview King Suite - Accessible) | Premium bedding, pillowtop beds, in-room safe, blackout drapes

Suite, 1 King Bed with Sofa bed, Accessible, Ocean View (Oceanview King Suite - Accessible)

  • Ocean view
  • 656 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Queen Sofa Bed
  • Free WiFi

View all photos for Family Villa, Oceanfront (Oceanfront Family Villa)

Balcony

Family Villa, Oceanfront (Oceanfront Family Villa)

  • Ocean view
  • 3100 sq ft
  • 4 bedrooms
  • Sleeps 10
  • 3 King Beds and 2 Twin Bunk Beds
  • Free WiFi

SUITE ONE BEDROOM Accessible

  • Sleeps 8
  • Free WiFi

1 Bedroom Oceanview Suite

  • Sleeps 2
  • Free WiFi

1 Bedroom Accessible Oceanview Suite

  • Sleeps 2
  • Free WiFi

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Chesapeake Beach Resort
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  • Pool
  • Breakfast included
  • Pet friendly
4.6 out of 5, Wonderful, 1,766 reviews
$209 nightly
The price is $235
Aug 25 - Aug 26
Total with taxes and fees
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About the neighborhood

Islamorada

With a stay at The Islands of Islamorada in Islamorada (Matecumbe), you'll be within a 10-minute walk of History of Diving Museum and Islamorada Brewery & Distillery. .This beach hotel is 0.8 mi (1.3 km) from Keys History & Discovery Center and 0.9 mi (1.4 km) from Lorelei Restaurant & Cabana Bar.

What's nearby

  • History of Diving Museum - 8 min walk - 0.4 miles
  • Islamorada Brewery & Distillery - 9 min walk - 0.5 miles
  • beach near Islamorada - 14 min walk - 0.8 miles
  • Keys History & Discovery Center - 15 min walk - 0.8 miles
  • Lorelei Restaurant & Cabana Bar - 18 min walk - 1.0 mile

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 40 min drive

Restaurants

  • ‪Hog Heaven - ‬4 min drive
  • ‪Lazy Days Restaurant - ‬5 min drive
  • ‪Wahoo's Bar & Grill - ‬19 min walk
  • ‪Islamorada Fish Company - ‬3 min drive
  • ‪Papa Joe’s Waterfront - ‬5 min drive

About this property

The Islands of Islamorada

The Islands of Islamorada offers 30 air-conditioned accommodations, which are accessible via exterior corridors and feature laptop-compatible safes and coffee/tea makers. Rooms open to furnished balconies or patios. These individually decorated and furnished accommodations have separate sitting areas. Pillowtop beds feature premium bedding. Smart televisions come with premium cable channels and Netflix. Bathrooms include showers with rainfall showerheads, bathrobes, designer toiletries, and complimentary toiletries.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include phones along with free local calls (restrictions may apply). Additionally, rooms include hair dryers and irons/ironing boards. In-room massages and hypo-allergenic bedding can be requested.

A marina and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site along with a hot tub. Other recreational amenities include a 24-hour fitness center.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guests can pamper themselves by indulging in the onsite spa services. Services include deep-tissue massages and Swedish massages.
Make yourself at home in one of the 30 individually decorated guestrooms, featuring microwaves and Smart televisions. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers with rainfall showerheads and designer toiletries.
Dip into one of the 2 outdoor pools or enjoy other recreational amenities including a 24-hour fitness center and 2 outdoor pickleball courts. This hotel also features complimentary wireless internet access, concierge services, and wedding services.
Wrap up your day with a drink at the poolside bar. Cooked-to-order breakfasts are available daily from 9:00 AM to 11:00 AM for a fee.
The front desk is staffed during limited hours. Free self parking is available onsite.
Cooked-to-order breakfasts are available for a surcharge and are served each morning between 9:00 AM and 11:00 AM.

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Free covered self parking on site

Food and drink

  • Daily cooked-to-order breakfast available 9:00 AM to 11:00 AM for a fee: USD 12 to 18 for adults and USD 12 to 18 for children
  • A poolside bar

Things to do

  • 2 outdoor pickleball courts
  • 2 outdoor pools
  • 24-hour gym
  • Beach volleyball
  • Beach yoga
  • Boat and paddles
  • Fishing
  • Free bicycle rentals
  • Games
  • Hot tub
  • Kayaking
  • Paddleboard
  • Pedal boat
  • Playground
  • Rafting
  • Rowing/canoeing
  • Water sports equipment

Family friendly

  • 2 outdoor pools
  • In-room microwave
  • Playground
  • Travel crib

Conveniences

  • Guidebooks
  • Limited-hour front desk

Guest services

  • Concierge services
  • Tour and ticket assistance
  • Wedding services

Outdoors

  • Barbecue grill
  • Beach loungers
  • Beach towels
  • Beach umbrellas
  • Dock
  • Firepit
  • Garden
  • Marina
  • On the beach
  • Outdoor furniture
  • Pool loungers

Spa

  • Deep-tissue massages
  • In-room massages
  • Prenatal massages
  • Swedish massages

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Area rugs in room
  • Elevator
  • Magnifying mirror
  • Tile flooring in room
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible pool

More

  • Smoking not allowed

Room amenities

Bedroom

  • Blackout drapes
  • Hypo-allergenic bedding
  • Pillowtop mattress
  • Premium bedding

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Rainfall showerhead
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Hulu
  • Netflix
  • Smart TV with premium cable channels
  • Streaming services

Food and drink

  • Coffee/tea maker
  • Electric kettle
  • Microwave
  • Paper towels

More

  • Access via exterior corridors
  • Air conditioning
  • Free local calls
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • Laptop-compatible safe
  • Phone
  • Separate sitting area

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: anytime
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

The front desk is open daily from 7:30 AM - 7:00 PM
Guests will receive an email within 2 weeks before arrival with check-in instructions and an access code; front desk staffed during limited hours
To make arrangements for check-in please contact the property at least 24 hours before arrival using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools

Access methods

Access code, front desk (limited hours)

Pets

Pets not allowed (service animals are welcome, and are exempt from fees)

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are not available

Property payment types

Important information

Optional extras

  • Fee for cooked-to-order breakfast: approximately USD 12.00 to 18 for adults, and USD 12.00 to 18.00 for children

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards; cash is not accepted
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is professionally cleaned

We should mention

Pool access available from 8:00 AM to 6:00 PM
Reservations are required for massage services and spa treatments; reservations can be made by contacting the property prior to arrival, using the contact information on the booking confirmation

Property is also known as

The Islands of Islamorada Villa
The Islands of Islamorada Islamorada
The Islands of Islamorada Villa Islamorada

The Islands of Islamorada Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 68 out of 80 reviews
Rating 8 - Good. 7 out of 80 reviews
Rating 6 - Okay. 4 out of 80 reviews
Rating 4 - Poor. 1 out of 80 reviews
Rating 2 - Terrible. 0 out of 80 reviews

10/10

Cleanliness

10/10

Staff & service

9.4/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Michael

Liked: Cleanliness, check-in, communication, listing accuracy
What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Kenneth

Liked: Cleanliness, check-in, communication, listing accuracy
Phenomenal hotel, Marcel and Jackie were amazing with the kids and the activities offered. This is the first hotel where I feel there is great value in the resort fee with all that's included.
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Janet

Liked: Cleanliness, room comfort, communication
Beautiful accommodations and location, very clean, many activities available at resort
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

Beth

Liked: Cleanliness, amenities, property conditions & facilities, communication
This place exceeded my expectations. Such a beautiful and quiet setting. Don't want to leave, but I will definitely be backa a beautiful
Stayed 4 nights in Feb 2026
Verified review

6/10 Okay

Shannon Myers

Liked: Cleanliness
Disliked: Listing accuracy
The "suite" was a single room with a king and pullout sofa, there was no separation. So if you are traveling with children be aware that this is the same as a double queen at any other hotel room.
Stayed 5 nights in Apr 2026
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, room comfort, communication
Amazing stay, can’t wait to stay there again!
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Ryan

Liked: Cleanliness, property conditions & facilities, communication
Beautiful property with great staff!
Stayed 4 nights in Jan 2025
Verified review

10/10 Excellent

Dixania

Liked: Cleanliness, amenities, property conditions & facilities, communication
Great for family vacation with kids. love it
Stayed 1 night in Oct 2025
Verified review

10/10 Excellent

Betty

Liked: Cleanliness, room comfort, communication
Beautiful property!
Stayed 1 night in May 2025
Verified review

10/10 Excellent

Craig

Liked: Cleanliness, amenities, property conditions & facilities, communication
Absolutely outstanding resort. Legitimate 5 star property.
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

John Aloysius

Liked: Cleanliness, amenities, property conditions & facilities, communication
Lovely room with friendly staff.
Stayed 4 nights in Jan 2025
Verified review

10/10 Excellent

Corey

Liked: Cleanliness, amenities, property conditions & facilities, communication
A beautiful property with GREAT customer service
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

Laura

Liked: Cleanliness, amenities, property conditions & facilities, communication
Such a beautiful, quiet and clean location. The staff were attentive and helpful.
Stayed 7 nights in Apr 2025
Verified review

10/10 Excellent

John

Liked: Cleanliness, amenities, property conditions & facilities, communication
Beautiful place and wonderful staff! We love Islamorada and can’t think of a better place to stay with a large family or crew.
Stayed 7 nights in Mar 2024
Verified review

10/10 Excellent

Ben

Liked: Cleanliness, amenities, property conditions & facilities, communication
Excellent resort. Hard working, friendly staff.
Stayed 8 nights in Sep 2023
Verified review

10/10 Excellent

amy

Liked: Cleanliness, property conditions & facilities, communication
What a beautiful place! Our room was perfect! The entire property was wonderful!
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

Diane

Liked: Property conditions & facilities, communication
Most restful, most excellent!!!
Stayed 4 nights in Jan 2025
Verified review

10/10 Excellent

Anze

Liked: Cleanliness, amenities, communication
Great property. Very comfortable and luxurious. The bar and food options can delivered to the room and very tasty! Really enjoyed the stay. Charlene was a great bartender by the pool!
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Cassie

Liked: Cleanliness, amenities, property conditions & facilities, communication
This property was immaculate, a great blend of an upscale hotel feel with a vacation rental. We loved all the amenities. Would highly recommend!
Stayed 3 nights in Jan 2025
Verified review

8/10 Good

Frank

Liked: Cleanliness, property conditions & facilities, communication
i like the fact that there's beach area but it was difficult to walk in an out of it due to the rocks. The pool filter could have been cleaned during our stay as there was multiple days of debris caught in the drain trap. would have enjoyed more dining options. Room was available before check in time which was appreciated and property/ room was very clean and maintained
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Earl

Liked: Cleanliness, amenities, property conditions & facilities, communication
We loved the entire experiences; especially the amenities on site (kayaks, paddle boards, swimming-pool & ocean, food & bar) and Emmanuel (person responsible kayaks and paddle boards).
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, room comfort, communication

Exceptional Vacation Property

The property was amazing & our Villa was exceptional! We had a wonderful time! The staff & service they provided was exceptional! They took care of our every need & were very prompt. The Villa was super clean & looked like it was brand new. Having stayed at many high end properties in Islamorada, this was the best!
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

susan

Liked: Cleanliness, room comfort, communication

Great stay at the Islands if Islamoralda!

Fantastic stay at the Islands! Beautiful, immaculately clean villa and property. Art work in the villas was outstanding! Very responsive staff.
Stayed 5 nights in Dec 2022
Verified review

10/10 Excellent

Katherine

Liked: Cleanliness, amenities, property conditions & facilities, communication
Everything was perfect. Every detail has been thought of. The rooms were immaculate and so well decorated. The property is really well maintained. We loved all of the games around the resort as well. Highly recommend!
Stayed 5 nights in Apr 2025
Verified review

10/10 Excellent

Diane

Liked: Cleanliness, communication
Perfect!!!
Stayed 1 night in Jan 2025

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