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Vacation Rentals in Islamorada, FL

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All 142 Rentals in Islamorada
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From
$99
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
23 photos Details Reviews (1) Make Inquiry
From
$200
Per Night
Studio, 1 Bathroom, Sleeps 2
13 photos Details Reviews (19) Make Inquiry
From
$300
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
7 photos Details Make Inquiry
Also consider
WELCOME TO PARADISE - ISLAMORADA VACATION RENTAL
2 Bedrooms, sleeps 6
$67 - $93 / night
76190 Overseas Highway - Casa Dorado
4 Bedrooms, sleeps 8
$857 - $1,000 / night
194 Gulfview Drive - 28 Night Minimum
3 Bedrooms, sleeps 6
$150 / night
SUNSET SERENITY
3 Bedrooms, sleeps 8
$5,500 - $7,500 / month
From
$1,599
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 10
33 photos Details Make Inquiry
From
$314
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
21 photos Details Make Inquiry
From
$214
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
25 photos Details Make Inquiry
From
$325
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
9 photos Details Make Inquiry
From
$500
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
8 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed August 26, 2014
We had a great stay! Ended up renting both houses for a weekend stay. Had 15 people and 4 boats. We had a great weekend, Helen and her son Rob were very accommodating and quickly...
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From
$200
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
21 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 2, 2014
Looked far and wide for a place in the keys that was on one level for my mom that uses a walker. Finally found the one! The owner is very helpful and communicative and worked...
5 of 5 stars Reviewed January 24, 2014
This condo exceeded our expectations. It was truly a home away from home. It has all the amenities you will need to have a great vacation. The kitchen is fully furnished, the...
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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...
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From
$275
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
27 photos Details Reviews (3) Make Inquiry
From
$145
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
26 photos Details Make Inquiry
From
$150
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details Make Inquiry
From
$145
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details Make Inquiry
From
$120
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
23 photos Details Reviews (15) Make Inquiry
5 of 5 stars Reviewed August 11, 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 August 3, 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
$286
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
16 photos Details Reviews (5) Make Inquiry
From
$115
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
6 photos Details Reviews (2) Make Inquiry
3 of 5 stars Reviewed June 12, 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 April 25, 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
$300
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
35 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed January 6, 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
$975
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 10
20 photos Details Make Inquiry
From
$275
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details Make Inquiry
From
$110
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
29 photos Details Make Inquiry
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...
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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...
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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...
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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...
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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...
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From
$107
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details Reviews (11) Make Inquiry
5 of 5 stars Reviewed July 9, 2014
Stayed here the last week in June with my wife, two kids and granddaughter. Room was clean and well laid out but a little bit cramped for the number of people. Closet space was...
5 of 5 stars Reviewed May 26, 2014
The condo was nicer and larger than we expected. It had everything we needed plus a few surprises: beach chairs and a float, very comfortable beds, and quiet neighbors. Also...
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From
$12,000
Per Month
3 Bedrooms, 3 Bathrooms, Sleeps 8
17 photos Details Reviews (2) Make Inquiry
From
$800
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
45 photos Details Reviews (2) Make Inquiry
From
$185
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
6 photos Details Reviews (3) Make Inquiry
4 of 5 stars Reviewed July 7, 2014
The pool is sparkling clean. You can enjoy the ocean-view from the pool area. The balcony is a wonderful place to hang out and relax. Close to everything.
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From
$6,000
Per Week
5 Bedrooms, 6 Bathrooms, Sleeps 10
22 photos Details Make Inquiry
From
$6,500
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 8
14 photos Details Make Inquiry
From
$22,000
Per Month
5 Bedrooms, 6 Bathrooms, Sleeps 10
15 photos Details Make Inquiry
From
$640
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 9
11 photos Details Reviews (4) Make Inquiry
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...
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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...
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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!
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From
$1,500
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details 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...
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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...
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Book Online(23)
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Suitability

  • Wheelchair access (12)
  • Elder access (29)
  • Suitable for children (45)
  • Pet friendly (32)
  • Smoking allowed (2)

Amenities

  • Grill (118)
  • Internet (116)
  • Air Conditioning (103)
  • Other outdoor space (102)
  • All pools (85)
  • View all amenities
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Book Online(23)

Suitability

  • Wheelchair access (12)
  • Elder access (29)
  • Suitable for children (45)
  • Pet friendly (32)
  • Smoking allowed (2)

Amenities

  • Grill (118)
  • Internet (116)
  • Air Conditioning (103)
  • Other outdoor space (102)
  • All pools (85)
  • View all amenities