Holiday Homes in Florida Keys

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Featured Holiday Homes in Florida Keys and around

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (98)
"We loved the location of the property and we also loved the entertainment/singer provided by lounge."
The Hammocks at Marathon

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

9.8 out of 10, Exceptional, (48)
"House was spotless, very bright and open! We really enjoyed the pool and even saw a few manatees in the canal! Great location, will be returning next time we’re in the Florida Keys!"
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Vacation with attitude!

10.0 out of 10, Exceptional, (7)
"Good location, family friendly, very nice pool and outdoors. "
Vacation with attitude!

Florida Keys vacation home, Family sized and pet friendly home with a pool!

10.0 out of 10, Exceptional, (19)
"Very clean, welcoming, and just what we needed for our get-away! "
Florida Keys vacation home, Family sized and pet friendly home with a pool!

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

9.6 out of 10, Exceptional, (57)
"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (77)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is €613
includes taxes & fees
18 Aug - 19 Aug
Old Florida Style, wrap around porch, boat basin for dockage, open water

Charming Home in Key Largo

9.8 out of 10, Exceptional, (23)
"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "
The price is €364
includes taxes & fees
13 Aug - 14 Aug
Charming Home in Key Largo

Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>

8.4 out of 10, Very good, (90)
"Well maintained, exceptional location, The management responded immediately to any concern. This was a toughly enjoyable vacation. "
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

8.8 out of 10, Excellent, (85)
"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "
The price is €641
includes taxes & fees
16 Aug - 17 Aug
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (72)
"Great tiny house, enjoyed our stay"
The price is €324
includes taxes & fees
25 Aug - 26 Aug
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

GREAT FAMILY VACATION HOME~Canal-Private Pool~ Dock, Bait Freezer & ICE MACH~

10.0 out of 10, Exceptional, (38)
"Great experience. Would definitely rent again!"
GREAT FAMILY VACATION HOME~Canal-Private Pool~ Dock, Bait Freezer & ICE MACH~

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

2.5 star property
10.0 out of 10, Exceptional, (18)
"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

208 Mariners Club Key Largo | 3 Bed, 3 Bath

9.8 out of 10, Exceptional, (87)
"We had a Wonderful time! There was plenty of space for our family of five. We had a few minor issues with ants, but it did not impact our comfortable stay. We loved the pool and Pickleball court! Would highly recommend. "
208 Mariners Club Key Largo | 3 Bed, 3 Bath

Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing

10.0 out of 10, Exceptional, (1)
"Beautiful property with a lot of space. Very well stocked with more than what you even think you need. Mariners Club is very nice with two great pools, a game room, marina, and pickleball courts. Only thing to note is there’s no beach access if that’s what you are looking for."
Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing

Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!

9.8 out of 10, Exceptional, (71)
"Our stay was amazing, the house had EVERYTHING we needed for our trip. Perfect location, beautiful scenery. Just perfect "
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!

Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.

10.0 out of 10, Exceptional, (8)
"Comfortable place in a nice neighborhood with a beautiful view"
Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

9.6 out of 10, Exceptional, (57)
"It was a beautiful home and Francine, our host, was most accommodating."
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (65)
"Such a great little property in a awesome community! A from the host he was such a nice person and communicating was superior would definitely rent again! "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Palm Villa - Sleeps 6, Boat Slip Available

9.8 out of 10, Exceptional, (138)
"Great trip. Very comfortable for family of 5. Cabana club lovely and great recommendations!"
Palm Villa - Sleeps 6, Boat Slip Available
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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Top Florida Keys Hotel Reviews