Search Vacation Homes in Islamorada

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Compare 748 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, (54)
"Clean, roomy and well stocked!"
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!

9.4 out of 10, Exceptional, (97)
"It was a good stay… thank you for having us."
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

10.0 out of 10, Exceptional, (191)
"Great stay, place was very comfortable. Our family enjoyed the property. "
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.

9.8 out of 10, Exceptional, (126)
"We enjoyed staying here. Plenty of space to spread out with the family. Clean and organized. Great location to the lagoon and pool."
Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

10.0 out of 10, Exceptional, (81)
"Amazing stay, property was exactly as advertised and had everything we needed."
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

2.5 star property
10.0 out of 10, Exceptional, (8)
"It was wonderful and relaxing beautiful area. Great host gave us lots of great information and local attractions."
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (111)
"Our family all thought this was the perfect spot for our famuly vacation"
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS! KAYAKS, MARINA, TENNIS

9.8 out of 10, Exceptional, (123)
"Cute community with nice accommodations. Kid friendly. Would stay again sometime!"
VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS! KAYAKS, MARINA, TENNIS

BEACHFRONT POOL HOME

9.6 out of 10, Exceptional, (103)
"The place was just as pictured & described. Lots of space, lots of amenities and lots of fun had by our group of 13!"
BEACHFRONT POOL HOME

BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

10.0 out of 10, Exceptional, (104)
"Well kept property. Great location. The owner is very responsive and did a great job preparing the property for our stay "
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

9.4 out of 10, Exceptional, (93)
"We had the best week at Shanie's lovely house! Location is even prettier in person!! The pool was always warm and clean, thanks to JP. We would definitely visit again."
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More

10.0 out of 10, Exceptional, (4)
"The house is beautiful and so clean. We had an amazing time"
4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More

Paradise Point 11- Brand new 3 bed 3 bath Oceanfront home with a rooftop balcony

The price is AED 2,388
AED 5,128 total
includes taxes & fees
27 Apr - 28 Apr
Paradise Point 11- Brand new 3 bed 3 bath Oceanfront home with a rooftop balcony

Islamorada Boaters Paradise with 70' Dock and private beach access..

10.0 out of 10, Exceptional, (21)
"Everything was amazing for our stay. We were able to have the boat right at the house for easy access for sunset boat rides and our everyday fishing adventures. "
Islamorada Boaters Paradise with 70' Dock and private beach access..

Mariners Club 806! your perfect 5-star vacation home w pools, pickleball & more

10.0 out of 10, Exceptional, (65)
"We enjoyed our stay and the amenities were great!. The condo was clean and very secure. We would stay here again."
The price is AED 1,377
AED 3,631 total
includes taxes & fees
29 Apr - 30 Apr
Mariners Club 806! your perfect 5-star vacation home w pools, pickleball & more

Anglers Reef Islamorada 2/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool

9.8 out of 10, Exceptional, (49)
"My family really enjoyed our stay for two weeks in Angler's Reef. We loved how there was room for everyone. The community where the home was nice and private. The kids enjoyed the pool and easy acces to the beach. The pool was heated which made it nice going into. There was plenty of food options nearby. We will definitely come back when we visit the keys again. "
Anglers Reef Islamorada 2/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool

Oceanfront, 2 Pools, Lagoon, Tennis, Picketball, Marina, Fishing & Great Views!

9.8 out of 10, Exceptional, (124)
"We had a wonderful stay at this property! The unit's location was fantastic and we truly enjoyed our time here. The beautiful views were slightly diminished by windows that needed cleaning, and while the beds could have been more comfortable and the dishwasher is due for replacement, these were minor issues in an otherwise great experience. Despite these small drawbacks, we would definitely stay here again."
Oceanfront, 2 Pools, Lagoon, Tennis, Picketball, Marina, Fishing & Great Views!

Villa Largo Island Retreat

9.4 out of 10, Exceptional, (33)
"There were a few maintenance issues, but nothing that got in the way of my group having a great time. Owner very responsive and helpful. We would definitely stay again. "
Villa Largo Island Retreat

Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

2.5 star property
9.4 out of 10, Exceptional, (8)
"Great place to stay. Great location and super clean."
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

Beach Residence / Private overwater dock / Heated Pool / Mahi Key

Beach Residence / Private overwater dock / Heated Pool / Mahi Key
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, (459)
"Great location, clean, room was modern with everything you need, nice pool area and beautiful views... Perfect stay for a family!!"
The price is AED 448
AED 562 total
includes taxes & fees
27 Apr - 28 Apr
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (58)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is AED 1,956
AED 2,403 total
includes taxes & fees
11 May - 12 May
The Islands of Islamorada

Beach Residence / Private overwater dock / Heated Pool / Mahi Key

Beach Residence / Private overwater dock / Heated Pool / Mahi Key
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.