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Compare 772 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)
"It was a very nice stay! Enjoyed the colorful fish in the lagoon, and the big lobster! It was a short walk to the jetty and beach."
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Villa Largo Island Retreat

9.4 out of 10, Exceptional, (32)
"Nice place, very clean, lovely decor. We arrived after dark and had a very hard time finding the unit as the lighting was not good, so unable to see the unit #'s. Also, I may have missed it in the description, but we didn't realize until we got there that this is on 3 floors. We're older, but still in pretty good shape, so were able to do the stairs to go in & out, up & down to bedroom, however I wouldn't think this would be a good match for anyone with young children, or people who have...
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

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

9.6 out of 10, Exceptional, (77)
"Great stay, lovely setting and location! Our second time here!"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

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

2.5 star property
10.0 out of 10, Exceptional, (6)
"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

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

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, (187)
"The condo is in a great location and is just as advertised! We were 110% happy with choosing this lovely place to stay in Key Largo. Christopher was very courteous and quick with responding to any questions we had. The condo was extremely clean and modern with everything we needed provided. Beds were so comfortable and we just had the best time!!! Great location too!!!! Thanks for a wonderful time!"
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

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

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

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

9.8 out of 10, Exceptional, (121)
"Beautiful place, loved the patio over looking the camel, and the upper deck, you can see out to the ocean. So pretty. The place is very clean, nice sized bedrooms and 3 bathrooms was fantastic for the group of us to each have their own bathroom. Very nice to have available to us pool toys, bikes and the golf cart was very nice to use and came in Handy when going to the pool. Great place to stay!! You will love it. "
Oceanfront, 2 Pools, Lagoon, Tennis, Picketball, Marina, Fishing & Great Views!

BEACHFRONT POOL HOME

9.4 out of 10, Exceptional, (100)
"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

Charming Home in Key Largo

9.8 out of 10, Exceptional, (12)
"Everything worked well. We didn't realize we needed a car so that was our one downfall. Beaches are private so ended up getting a lot of Ubers. Check in was smooth and communication was easy. Also, didn't realize no beach towels - live a learn! Thank you! "
Charming Home in Key Largo

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

Peacock Shores Islamorada - Vacation On The Beach!

10.0 out of 10, Exceptional, (33)
"Great place! Second time staying here. Comfortable, very clean, quiet and close to many great restaurants."
Peacock Shores Islamorada - Vacation On The Beach!

Kawama L4 - Upscale Oceanside Villa with Marina

9.6 out of 10, Exceptional, (133)
"Loved the unit and the whole property. Loved up to the hype!"
Kawama L4 - Upscale Oceanside Villa with Marina

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

10.0 out of 10, Exceptional, (46)
"Our family enjoyed this house. The host was extremely helpful when I needed to contact her. Overall, the house was exactly as described. Particularly, I enjoyed the availability of the extra towels and we also enjoyed the quality beach towels available.The house had the amenities we needed to enjoy our week in the Florida Keys. The notebook on the counter offered plenty of suggestions for restaurants and things to do. Thank you for the fantastic stay!"
Anglers Reef Islamorada 2/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool

3BR/3.5BA Mariner's Club Townhouse 711 with Oasis Pool, Marina, Game Room & More

10.0 out of 10, Exceptional, (2)
"Nice home, 3 floors provided privacy yet enough open space to be together. Amazing pool "
3BR/3.5BA Mariner's Club Townhouse 711 with Oasis Pool, Marina, Game Room & More

Spectacular Mariners Club w pools & pickleball! Spring Dates Open: 4/5-4/14

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 2,138
SAR 4,438 total
includes taxes & fees
18 Apr - 19 Apr
Spectacular Mariners Club w pools & pickleball! Spring Dates Open: 4/5-4/14
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, (428)
"Very clean! The location on the water is beautiful. We certainly would stay here again."
The price is SAR 896
SAR 1,203 total
includes taxes & fees
16 Apr - 17 Apr
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (53)
"Above and beyond service. "
The price is SAR 2,172
SAR 2,650 total
includes taxes & fees
6 Apr - 7 Apr
The Islands of Islamorada

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
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.