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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, (50)
"Easy to get to everything. Wonderful unit. Well stocked, clean & comfortable. Bedrooms both upstairs so be prepared for that. Made it difficult with bad knee but bathroom on each floor made it work."
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, (96)
"Pool was warm, kids loved to see the fish in the lagoon. Walked out to the ocean morning and night. Would have loved to kayak down by the ocean but there were no paddles. Walking distance to great restaurants."
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, (188)
"We had a great time in Key Largo relaxing with our family of five. The unit was perfect and an oasis from life. They created a perfect and comfortable environment. The development is quaint and quiet. "
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, (123)
"We were 3 families that had a very relaxing stay at the Kawama house. Very safe gated community with private beach, pool, playground and own golf cart which made our trips to the beach and fire pits very convenient. Owner addressed a couple of small issue with cleanliness (unit not used for 2 months) and golf cart very quickly. Beds were comfortable, kitchen equipped with everything we needed, the enclosed balcony very cozy. Intend to go back. "
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

9.8 out of 10, Exceptional, (79)
"Three generations of our family enjoyed a wonderful vacation at The Last Resort. The house was beautifully appointed and well stocked as described in the listing. It had everything we needed for a memorable beach vacation. The owner was friendly, helpful, and easy to communicate with. We hope to return! back!ThownerfrieThowwith. "
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, (7)
"This condo and the club is awesome. The pool is wonderful. We loved everything about or stay would come back! "
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (109)
"Beautiful bay views, manatees galore, fishing off the sea wall, enough dockage for our 22 & 18 ft boats. 3 excellent master suites with great bathroom showers. Kitchen, dining room and family room all open to each other and great for gathering. Perfect pool, waterside chairs & firepit.Highly recommend!!"
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, (120)
"This unit, is a two-story condominium with a “great room“ on the ground floor and bedrooms upstairs. The larger bedroom has a king size bed and bunk beds making it perfect for a family with 2 children. The second room accommodates 2 people well, and has a large west facing deck off the room for lovely sunsets.There is an enclosed patio that leads out to a small yard area with lounge chairs. It was very nice to be able to sit out in the evening after the children went to bed. There are two...
VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS! KAYAKS, MARINA, TENNIS

BEACHFRONT POOL HOME

9.6 out of 10, Exceptional, (101)
"The home was wonderful for our group of 12. The property is beautiful and the pool and hot tub were perfect. "
BEACHFRONT POOL HOME

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

10.0 out of 10, Exceptional, (104)
"Our stay was pure delight! The home was exceptionally clean, comfortable, and beautifully decorated. The kitchen was well stocked and having use of the golf cart made it easy to head down to the point for fishing or a beautiful sunset. Check in and communication with the owner was a breeze. The home is close to everything Key Largo has to offer. I definitely recommend this property as we have it on our list to come back!"
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, (89)
"We were fortunate to get just one day of rain, and otherwise had wonderful weather, which was great because the outdoor space at this property is wonderful. There is a large area to play soccer or throw a ball, as well as beach, long and low dock, and kayaks to use. The outside space is truly what makes this house special. The location is very good and easy to get to -- you're just a handful of miles from some of the more touristy things in Islamorada, making this a quiet spot that still has...
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)
"Property was beautiful and perfectly fit our needs for our business fishing trip! "
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

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)
"House was perfect for our Keys vacation! We were able to bring our 23ft Key West and keep it docked at the house. The house had a pool, hot tub, ice machine, fish cleaning table. Plus right down the canal is an amazing sandbar. Highly recommended this place if you have a boat. House was not far from great restaurants like Hungry Tarpon, Lazy Days & Papa Joes"
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)
"This was the perfect house and location for our quick getaway from Cold MI!"
The price is SAR 2,344
SAR 4,827 total
includes taxes & fees
18 Apr - 19 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, (47)
"Overall we had a great experience, house was accommodating and clean for the most part. The house is located in an overall quiet neighborhood perfect for family and kids. It is also in close proximity to family activities. One downfall would be the noise from US1 behind the house and the garbage that comes 2x a week before 5am. I would definitely recommend sound machines at night to help drown out some of the noise. "
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, (122)
"The freezer didn't make ice, the gate keeper was confusing, gulf cart needs updating. I think that the stairs should be described more in the listing. Over all we had a great stay. Would stay again. Loved the lagoon. "
Oceanfront, 2 Pools, Lagoon, Tennis, Picketball, Marina, Fishing & Great Views!

Villa Largo Island Retreat

9.4 out of 10, Exceptional, (33)
"Location was great one hour from Miami airport and lots to do on island. We did snorkeling, deep sea fishing and rented jet skis. Nice restaurants on both Key Largo and Islamorada. Property was nice loved the lagoon, pools, jetty. We saw Manatees in the marina. House was nice but floors could have been cleaner. No soap or dishwasher soap provided so be prepared to bring your own. "
Villa Largo Island Retreat

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

2.5 star property
9.8 out of 10, Exceptional, (6)
"Overall stay good. Spacious and easy access."
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

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

The price is SAR 4,498
SAR 7,986 total
includes taxes & fees
13 Apr - 14 Apr
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, (431)
"The rooms and patio were very clean, recently remodeled, walkable to a few nice restaurants. Parking was easy. No area for swimming but great space with chairs to relax for sunrise and open space for lounging. Huge iguanas on the docks. The mattress Seemed new but very firm. "
The price is SAR 684
SAR 829 total
includes taxes & fees
30 Mar - 31 Mar
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (54)
"Above and beyond service. "
The price is SAR 1,931
SAR 2,379 total
includes taxes & fees
6 Apr - 7 Apr
The Islands of Islamorada

OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

10.0 out of 10, Exceptional, (175)
"Rodger and Linda is home and Islamorada is wonderful. They are unbelievably accommodating property owners and made the trip extra special. I look forward to returning and staying there again."
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
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.