We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Islamorada, FL

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 146 Rentals in Islamorada
loading...
Sort by
From
$200
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
21 photos Details Reviews (2) Make Inquiry
From
$99
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
23 photos Details Reviews (1) Make Inquiry
From
$3,000
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
23 photos Details Reviews (1) Make Inquiry
Also consider
Oceanfrontparadise: 209
2 Bedrooms, sleeps 4
$145 - $250 / night
Sunset views at The Palms in Islamorada. Fully remodeled.
2 Bedrooms, sleeps 4
$71 / night
Islamorada- Very Private Oceanfront Estate
3 Bedrooms, sleeps 6
$543 / night
The Perfect Getaway
4 Bedrooms, sleeps 10
$3,000 / week
From
$2,400
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed May 28, 2013
The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough for...
See all reviews
From
$18,000
Per Month
4 Bedrooms, 3 Bathrooms, Sleeps 8
11 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed June 16, 2013
Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching...
See all reviews
From
$4,900
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
29 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed August 22, 2011
This property is a collection of 4 houses, 2 closer to the ocean, each with their own pool and three bedrooms (Conch and Pelican Houses), the other two behind, with no pool and...
See all reviews
From
$471
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
11 photos Details Reviews (1) Make Inquiry
From
$1,043
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 16
11 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed May 11, 2013
We booked this fabulous ocean front home for our 20th Anniversary as we decided to bring our four teenagers with us. This was the first time we had ever rented a vacation...
5 of 5 stars Reviewed March 6, 2013
We just returned from a week in Islamorada at the Southern Diversion estate. The property was just beautiful - from the tree lined drive up to the front of the home to the...
See all reviews
Get the List
From
$315
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
30 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed May 4, 2014
This vacation rental exceeded our already high expectations! We are a family of 4 adults and 3 children familiar with staying at Hawks Cay for our prior Easter vacations. We were...
5 of 5 stars Reviewed March 10, 2014
We exchanged to this Property through Club Paradiso which is based in Tenerife. We were in property 126, which is situated in the middle row of the complex.We had sea views from...
See all reviews
From
$157
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details Reviews (9) Make Inquiry
3 of 5 stars Reviewed March 4, 2014
This was a nice rental. There seems to have been a nice soft update done not to long ago, and it appeared that some features were still being upgraded. The building is clean...
5 of 5 stars Reviewed January 13, 2012
The condo was great! It was clean and located in a great place in the Keys. There were many excellent restaurants in the area when you wanted to go out, and a full kitchen when...
See all reviews
From
$185
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details Reviews (10) Make Inquiry
5 of 5 stars Reviewed February 2, 2013
My wife and I returned to this rental a little over a year after our first stay here because we liked it so much the first time. This year we arrived during business hours and...
4 of 5 stars Reviewed February 4, 2011
We really enjoyed staying at this house. When we first drove up, we were anxious because the houses on this street are nestled together closely. However, we stayed for over a...
See all reviews
From
$500
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
38 photos Details Reviews (22) Make Inquiry
5 of 5 stars Reviewed May 19, 2013
This home was the perfect location for our spring break vacation. It was so central to many activities on the keys and so many wonderful restaurants. The home is very nice, a...
5 of 5 stars Reviewed January 20, 2013
I recently returned from Islamorada where the weather was low 80s and sunny every day. JoAn and Barbara were exceedingly helpful. The house was perfect for the needs of six of...
See all reviews
From
$700
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed January 6, 2014
I traveled with my partner and another couple. We enjoyed the comfortable roomy accomodations. Loved the convenience of cooking meals. The grounds are beautiful. We enjoyed the...
See all reviews
From
$640
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 9
11 photos Details Reviews (4) Make Inquiry
From
$2,975
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 6
49 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed May 13, 2014
We had such a wonderful time at Paradise Point!! The views were beautiful!!! The kids loved the pool and all the sealife we saw. Many fish and stingrays, just to name a few...
5 of 5 stars Reviewed February 13, 2014
My week started when my wife and I along with our two friends met Juan Sanchez at this home he calls Paradise (which it really is). The man from my first e mail to him to locking...
See all reviews
From
$300
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 5
29 photos Details Reviews (22) Make Inquiry
5 of 5 stars Reviewed August 20, 2014
We fell in love with the villa the minute we walked in through the door. Everything was immaculate and extremely welcoming. The owner had thought about everything and the box of...
5 of 5 stars Reviewed June 30, 2014
This was the perfect place for a relaxing vacation with my extended family. The location was great, and close to all Islamorada has to offer. The pool was so nice, overlooking the...
See all reviews
From
$385
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed May 12, 2014
We loved staying at Villa Marlin, and the owner was very helpful before and during our stay. The home is prettier than the pictures, and we felt right at home!
See all reviews
From
$329
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
25 photos Details Reviews (6) Make Inquiry
4 of 5 stars Reviewed June 5, 2014
This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
4 of 5 stars Reviewed June 24, 2013
Have been going to Islamorada for years and this year planned a trip with 4 other friends and our dog. This was the perfect house. plenty of room for all of us. The views are...
See all reviews
From
$7,500
Per Month
3 Bedrooms, 1 Bathroom, Sleeps 6
10 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed December 2, 2013
We were so lucky to have visited this home during November. We had the whole private gated compound to ourselves and even though we only leased the Cottage, the owners were so...
See all reviews
From
$259
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details Reviews (1) Make Inquiry
From
$286
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
26 photos Details Reviews (6) Make Inquiry
From
$259
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed August 11, 2013
We completely enjoyed our stay. Plenty of room for 6 ppl to sleep. Nice sized kitchen and dining area. We stayed with two young children and they loved it. Great location for both...
See all reviews
From
$1,714
Per Night
10 Bedrooms, 10 Bathrooms, Sleeps 28
25 photos Details Reviews (11) Make Inquiry
5 of 5 stars Reviewed October 4, 2014
We wanted a simple wedding and then a week of fun with family and friends. Alligator Reef exceeded our expectations. We had a wedding ceremony with 25 guests under the palm...
5 of 5 stars Reviewed May 22, 2014
We had a great stay. The home was very clean and everything in it looked new. The beds all slept well. The location was wonderful. It has several cool places to eat nearby. We...
See all reviews
From
$6,500
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details Reviews (1) Make Inquiry
From
$850
Per Night
8 Bedrooms, 6 Bathrooms, Sleeps 16
7 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed March 26, 2014
The house was amazing! Just as the pictures show. We were traveling with 4 adults and 6 teenagers. There was always something for everyone to do. The property manager was friendly...
See all reviews
From
$134
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
9 photos Details Reviews (1) Make Inquiry
From
$5,000
Per Month
2 Bedrooms, 1 Bathroom, Sleeps 4
26 photos Details Reviews (2) Make Inquiry
From
$757
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
40 photos Details Reviews (16) Make Inquiry
2 of 5 stars Reviewed April 28, 2014
Everything seemed to be broken. The pool water had a green tint and was finally shocked by the pool guy. One of the closet doors was broken off and placed in the closet. One of...
3 of 5 stars Reviewed December 2, 2013
Yes, the house is great for large family but the amenities leave something to be desired. Appliances are dated, counter tops are tiled and grout appears dirty. Washer broke, oven...
See all reviews
From
$214
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details Reviews (15) Make Inquiry
4 of 5 stars Reviewed August 3, 2014
Nice townhome with water view, easy drive to activities in Islamorada, Tavernier, and Key Largo. Townhome is 3 levels, lots of stairs, narrow staircases. Clean, updated, kitchen...
3 of 5 stars Reviewed July 31, 2014
Beautiful view but the highway is nearby and you hear a lot of traffic. The whole facility is quite nice but the condo itself is not in the best shape. Especially the kitchen is...
See all reviews
From
$200
Per Night
Studio, 1 Bathroom, Sleeps 2
13 photos Details Reviews (19) Make Inquiry
5 of 5 stars Reviewed September 8, 2014
Had a very relaxed we here with my partner just chilling out and doing very little except lying on the hammock watching the parrot fish swim by. The hosts are great friendly...
5 of 5 stars Reviewed June 21, 2014
Had a great time in a great location in the middle keys. This place has everything needed to have a lot of fun and relax at the same time. The tiki hut is nice to get out of the...
See all reviews
From
$5,250
Per Month
3 Bedrooms, 3 Bathrooms, Sleeps 8
24 photos Details Reviews (1) Make Inquiry
From
$1,040
Per Week
1 Bedroom, 2 Bathrooms, Sleeps 3
19 photos Details Reviews (2) Make Inquiry
From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
15 photos Details Reviews (6) Make Inquiry
From
$429
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
11 photos Details Reviews (7) Make Inquiry
4 of 5 stars Reviewed August 12, 2014
The home that we stayed at was incredible! The accommodations, the view, the boat dock space was all great. It was fast in and out to the Atlantic Ocean to be able to scuba...
5 of 5 stars Reviewed January 4, 2013
We stayed here for Christmas with 6 people (using 4 bedrooms). The main house has 3 bedrooms and the mother-in-law apartment across the deck has 2 bedrooms as well as a kitchen...
See all reviews
From
$4,000
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details Reviews (1) Make Inquiry
From
$214
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Reviews (3) Make Inquiry
4 of 5 stars Reviewed August 3, 2014
Nice townhome for reasonable price, reasonably updated, lots of narrow stairs - 3 level townhome. Quiet area, easy access to Islamorada, Tavernier, and Key Largo. Freewheeler...
See all reviews
From
$125
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
30 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed June 8, 2012
We had a medical emergency on the day of arrival to Anglers Reef, that required emergency surgery in Miami. Mike and his wife Blanka was by coincidence staying in their other...
5 of 5 stars Reviewed May 8, 2012
This place is a gem. Everything is as described and the owners very were kind and helpful. The community is gorgeous and you're instantly in vacation mode once you are inside the...
See all reviews
From
$147
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
18 photos Details Reviews (7) Make Inquiry
3 of 5 stars Reviewed April 8, 2013
We were going to bring our boat down from Miami but when we found out the hotel charges $3.00 per foot per day, we found that to be quite excessive...we are guests! One would...
See all reviews
From
$1,350
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
22 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed June 15, 2014
We spent a full week at this Futura Yacht Club rental, which we enjoyed very much. Here are the pro's and con's: Pro: Boat slip accommodated our 29 foot boat well Fresh water...
See all reviews
From
$500
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
15 photos Details Reviews (3) Make Inquiry
Go to map view
Book Online(24)
Use filters to find the best results!

Suitability

  • Wheelchair access (12)
  • Elder access (30)
  • Suitable for children (46)
  • Pet friendly (32)
  • Smoking allowed (2)

Amenities

  • Grill (122)
  • Internet (119)
  • Air Conditioning (108)
  • Other outdoor space (107)
  • All pools (80)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List

More Beach destinations:

More Family destinations:

Filter search results by:
Book Online(24)

Suitability

  • Wheelchair access (12)
  • Elder access (30)
  • Suitable for children (46)
  • Pet friendly (32)
  • Smoking allowed (2)

Amenities

  • Grill (122)
  • Internet (119)
  • Air Conditioning (108)
  • Other outdoor space (107)
  • All pools (80)
  • View all amenities