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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, (51)
"Enjoyed our stay. Lots to do if you’re wanting a relaxing day or a day of swimming, tennis, walking or cycling. "
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)
"Great place to experience Key Largo.. Everything was as seamless as you could hope for with no unexpected surprises for a short stay. "
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, (190)
"My husband, son, and daughter & family stayed here 4 nights. The 8 of us all had a fabulous time. The condo is beautiful and the pools and grounds are wonderful. Well worth it."
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)
"The condo was in a great location close to the pool, lagoon and ocean and easily accessible by golf cart. The home is newly renovated and has everything you need to cook, relax and enjoy your stay. Beds are super comfortable and the AC works great. Fast communication from management. Each floor has multiple balconies to take in the outdoors. You will not regret renting here! "
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)
"If you are lucky enough to find an opening for this house, just book it.The house and property are truly exceptional. Everything is thoughtfully labeled in the house, which is really handy when you just want to know what light switch turns on which light! The kitchen and bathrooms are VERY well stocked.The canal out back is very nice and my kids actually caught some cool fish out there. Manatees came to visit there are well. We loved the kayaks and paddle boards. The home is over 100 years old...
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, (111)
"Love Chausie and her properties! Top notch! "
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, (122)
"The property is well maintained and clean. It was a nice central location between Miami, the Everglades and Key West with nice dining options a quick walk away. The property manager Diana was very quick to respond to our questions."
VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS! KAYAKS, MARINA, TENNIS

BEACHFRONT POOL HOME

9.6 out of 10, Exceptional, (102)
"Another fantastic stay in an amazing spot!!"
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, (93)
"Would definitely stay here again. Absolutely peaceful and amazing and exactly what we needed! JP was extremely helpful, friendly and amazing as well. Great place "
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 SARĀ 2,308
SARĀ 4,780 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, (48)
"Angler’s Reef and the Blue Marlin House were wonderful places to stay. The property is very well appointed, the pool was family friendly and we met great people!"
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, (123)
"House as described. Beautiful home and location. Extremely clean. Has anything you need for beach/water activities. Property manager communicates promptly. Jose was very easy to deal with. Would definitely stay again."
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
9.6 out of 10, Exceptional, (7)
"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

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, (447)
"Location, ease of checkin. "
The price is SARĀ 413
SARĀ 659 total
includes taxes & fees
29 Apr - 30 Apr
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (55)
"Above and beyond service. "
The price is SARĀ 2,248
SARĀ 2,736 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.