Search Vacation Homes in Islamorada

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Compare 645 Vacation Homes in Islamorada with updated reviews, rates, and availability.

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
9.8 out of 10, Exceptional, (39)
"Property owner was exceptional to deal with and the property was very clean and cozy! The home had all the comforts of home. Enjoyed the pool, lagoon and my husband loved fishing off the jetty !! "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Villa Largo Island Retreat
9.6 out of 10, Exceptional, (29)
"This house was perfect for our families (4 adults and 3 toddlers). It was very relaxing, tons of space, and in a great location within walking distance to the shoreline. There was a playground, swimming pool, and a lagoon right outside our back door! Everything was beautiful and the host was very quick to respond to any questions we had. Definitely would recommend this property! "
Villa Largo Island Retreat
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!
9.6 out of 10, Exceptional, (89)
"We felt right at home! Great amenities on the property. The kids swam in the lagoon and at the small beach. Plenty of room for our family and the condo was very clean and welcoming. Our host was great about checking in to make sure our stay was excellent. We would recommend this home to other families!"
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
10.0 out of 10, Exceptional, (92)
"We enjoyed our long weekend in the Florida Keys with our two children (5 & 8). "
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- BEACH- POOLS-FISH
9.8 out of 10, Exceptional, (180)
"Great unit. Family oriented property. Great location."
NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- BEACH- POOLS-FISH
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
9.8 out of 10, Exceptional, (134)
"Had a wonderful holiday at this property, any issue was dealt with super quickly, lovely location with fantastic facilities all around. Would definitely recommend this property to all international travellers visiting the keys. Thanks for some amazing memories…. "
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
Casa Largo
9.0 out of 10, Wonderful, (122)
"The unit was updated and clean. Close to playground, lagoon, and pool. Centrally located in Key Largo, close to many restaurants."
Casa Largo
New Caribbean home. Resort access to pool
10.0 out of 10, Exceptional, (17)
"Me my wife and my brother and his wife rented the property for a week. The cottage and resort are top notch. We would and will stay again and recommend the property, five star week."
New Caribbean home. Resort access to pool
Marina-View 3BR/3BA Mariner's Club Townhouse 201 with Oasis Pool, Marina, Game Room & More
10.0 out of 10, Exceptional, (1)
"We (3 adults & 2 children (aged 15 & 12)) stayed for 5 nights and had a great time - we didn't want to leave! The resort is lovely and peaceful, there were hardly any other people staying there when we visited in October, the pools were great (although not that warm), watching sunrise from the pier was beautiful - and one of our party was lucky enough to see a manatee in the marina. The villa is generally well equipped and comfortable (v comfortable master bed) with good showers. Plenty of...
Marina-View 3BR/3BA Mariner's Club Townhouse 201 with Oasis Pool, Marina, Game Room & More
VOTED BEST KEY LARGO VACATION RENTAL
10.0 out of 10, Exceptional, (67)
"5 of us really enjoyed our stay. Norman provided great information to enjoy using their bikes, face masks 7 snorkels, etc. Best part was snorkeling in the private "swimming hole" lagoon, with beach stocked with tropical fish.' We all want to return "
VOTED BEST KEY LARGO VACATION RENTAL
Overlooking Salt-water Lagoon- Free Golf Cart + 2 Kayaks
9.8 out of 10, Exceptional, (24)
"The property was lovely. It was a great location and the neighborhood had great amenities. My only issue was that while it slept 6, there wasn't 6 seats at the dining table nor 6 places to sit in the living room. I would expect all aspects of a property to fit the same number of people that can sleep there."
Overlooking Salt-water Lagoon- Free Golf Cart + 2 Kayaks
4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More
10.0 out of 10, Exceptional, (3)
"The home was perfect for two families to stay comfortably. The home was well equipped with everything we needed and the kids loved the basket of items they could use at the basketball and pickle ball courts. The resort was clean and well managed. We will definitely return when visiting the area in the future. "
4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More
Beautiful Lagoon Front Townhome!
9.4 out of 10, Exceptional, (3)
"Great place to stay"
Beautiful Lagoon Front Townhome!
2BR/2.5BA Angler's Reef Conch Villa 103 With Private Beach and Pool Access
2BR/2.5BA Angler's Reef Conch Villa 103 With Private Beach and Pool Access
Cozy canal in the Keys - leads directly into crystal blue ocean! 🌊
10.0 out of 10, Exceptional, (2)
"The property manager Like Perry was great to work with, he answered every question quickly and thoroughly. He worked with us when we found we would be arriving before check in and was great. The house was wonderful and had all the necessary items to make the trip a breeze. It was truly like coming home, just in a different location."
Cozy canal in the Keys - leads directly into crystal blue ocean! 🌊
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
10.0 out of 10, Exceptional, (8)
"We really enjoyed this property and the amenities offered. Erick was great to work with and gave us a ton of ideas and options for local food and day trips. We will be back. Thank you for sharing your home!"
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
2.5 star property
10.0 out of 10, Exceptional, (1)
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH
9.8 out of 10, Exceptional, (154)
"The condo was inviting and a home away from home. Nice to have straight access to pool area from back patio. The pool was good size. No hot tub. Most days pool was not crowded except for Saturday afternoon and evening there was a large crowd that met there and had very loud music with that could be heard throughout condo with doors closed. You are able to hear your neighbors and kids from the condo if they are loud which most kids are . Having golf cart to go to the jetty beach side is very nice...
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH
TikiBar,HeatedPool,PriSpa,kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, and more
10.0 out of 10, Exceptional, (78)
"Our family of 5 had a great say here! All the details were exactly as expected. It's a charming house in a great location to explore all the Keys has to offer. We had a great trip in large part thanks to this property!"
TikiBar,HeatedPool,PriSpa,kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, and more
Newly renovated coastal home; Marina, Pools, Lagoon, Bikes, Tiki’s and More!
9.8 out of 10, Exceptional, (50)
"Plenty of room for our group of 8. Very clean and plenty of amenities. We loved the lagoon and pool. Key Largo is lovely and the condo is well situated. Highly recommend- would absolutely stay here again. Wishing I was still there!"
Newly renovated coastal home; Marina, Pools, Lagoon, Bikes, Tiki’s and More!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Islamorada

Breezy Palms Resort
2.5 star property
8.6 out of 10, Excellent, (371)
"Beautiful views "
The price is AED 406
AED 647 total
includes taxes & fees
24 Nov - 25 Nov
Breezy Palms Resort
The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (39)
"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)."
The price is AED 2,387
AED 2,686 total
includes taxes & fees
1 Dec - 2 Dec
The Islands of Islamorada
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
10.0 out of 10, Exceptional, (4)
"Our family of 5 stayed here over Christmas and had a wonderful time. The house had everything we needed. We hope to return soon!"
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.