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Vacation rentals in Islamorada, FL

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All 146 Rentals in Islamorada
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From
$561
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
8 photos Details Reviews (1) Make Enquiry
From
$225
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
21 photos Details Reviews (2) Make Enquiry
From
$1,516
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
22 photos Details Reviews (1) Make Enquiry
Also consider
Islamorada Tropical Escape! Clean, Affordable & Licensed for Weekly Rental!
2 Bedrooms, sleeps 6
$120 / night
Your Florida Keys Getaway
4 Bedrooms, sleeps 8
$401 / night
Islamorada 2-bedroom Condo
2 Bedrooms, sleeps 6
$208 / night
The Perfect Getaway
4 Bedrooms, sleeps 10
$3,369 / week
From
$111
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
23 photos Details Reviews (1) Make Enquiry
From
$225
Per Night
Studio, 1 Bathroom, Sleeps 2
13 photos Details Reviews (19) Make Enquiry
5 of 5 stars Reviewed 8 September 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 21 June 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...
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From
$337
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
35 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 6 January 2012
My husband and I stayed here for almost 2 weeks for our honeymoon/vacation over the Christmas holiday. We were nervous about renting something over the internet that we had never...
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From
$309
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
27 photos Details Reviews (3) Make Enquiry
From
$321
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
16 photos Details Reviews (5) Make Enquiry
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From
$135
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
23 photos Details Reviews (15) Make Enquiry
5 of 5 stars Reviewed 11 August 2014
My wife and I stayed a week at the Florida Bayside retreat and absolutely loved it. The condo was extremely clean and had a great view of the water. My wife and I also were...
5 of 5 stars Reviewed 3 August 2014
Fantastic location with wonderful views of the gulf. Very tranquil and peaceful in July. An extremely well equipped condo, lovely pool and landscaped gardens. Parking no issue and...
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From
$129
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
6 photos Details Reviews (2) Make Enquiry
3 of 5 stars Reviewed 12 June 2014
Location was great, quiet & relaxing. Close to shopping & restaurants. Allowed us to bring our elderly dog. Small but had everything you needed.
3 of 5 stars Reviewed 25 April 2014
You've got to like Key Islamarada because it's strictly for boaters and this place has a slip for yours. We booked it because it was one of the few rentals with handicapped...
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From
$1,095
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 10
20 photos Details Make Enquiry
From
$1,796
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 10
33 photos Details Make Enquiry
From
$353
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
21 photos Details Make Enquiry
From
$337
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
9 photos Details Make Enquiry
From
$309
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details Make Enquiry
From
$80
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details Make Enquiry
From
$240
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
25 photos Details Make Enquiry
From
$163
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
26 photos Details Make Enquiry
From
$365
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
9 photos Details Make Enquiry
From
$124
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
29 photos Details Make Enquiry
From
$168
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details Make Enquiry
From
$163
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details Make Enquiry
From
$20,212
Per Month
4 Bedrooms, 3 Bathrooms, Sleeps 8
11 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 16 June 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...
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From
$150
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
9 photos Details Reviews (1) Make Enquiry
From
$1,171
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 16
11 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 11 May 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 6 March 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...
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From
$5,502
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
29 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 22 August 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...
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From
$208
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details Reviews (10) Make Enquiry
5 of 5 stars Reviewed 2 February 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 4 February 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...
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From
$176
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details Reviews (9) Make Enquiry
3 of 5 stars Reviewed 4 March 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 13 January 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...
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From
$337
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 5
29 photos Details Reviews (22) Make Enquiry
5 of 5 stars Reviewed 20 August 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 30 June 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...
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From
$369
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
25 photos Details Reviews (6) Make Enquiry
4 of 5 stars Reviewed 5 June 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 24 June 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...
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From
$5,615
Per Month
2 Bedrooms, 1 Bathroom, Sleeps 4
26 photos Details Reviews (2) Make Enquiry
From
$432
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 12 May 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!
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From
$8,422
Per Month
3 Bedrooms, 1 Bathroom, Sleeps 6
10 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 2 December 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...
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From
$482
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
11 photos Details Reviews (7) Make Enquiry
4 of 5 stars Reviewed 12 August 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 4 January 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...
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From
$321
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
26 photos Details Reviews (6) Make Enquiry
From
$529
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
11 photos Details Reviews (1) Make Enquiry
From
$561
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
38 photos Details Reviews (22) Make Enquiry
5 of 5 stars Reviewed 19 May 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 20 January 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...
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From
$354
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
30 photos Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 4 May 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 10 March 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...
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From
$7,299
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details Reviews (1) Make Enquiry
From
$1,925
Per Night
10 Bedrooms, 10 Bathrooms, Sleeps 28
25 photos Details Reviews (11) Make Enquiry
5 of 5 stars Reviewed 4 October 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 22 May 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...
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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
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