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Vacation Homes in Florida Keys

The Hammocks at Marathon
Relax by the pool surrounded by palm trees and lounge chairs, with a boat on the water nearby.

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
5 bedrooms, pool/spa heated, bikes, kayaks, game room, elevator, deep 75' dock.
Exterior

5 bedrooms, pool/spa heated, bikes, kayaks, game room, elevator, deep 75' dock.

10.0 out of 10, Exceptional, (71)
"Great time with friends for the week. House was clean, pool and hot tub were amazing and the location was perfect !!! "
5 bedrooms, pool/spa heated, bikes, kayaks, game room, elevator, deep 75' dock.
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock
Exterior

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
Villa Coral, brand new, spectacular outdoor area!
Pool

Villa Coral, brand new, spectacular outdoor area!

9.8 out of 10, Exceptional, (25)
"Awesome stay! Very responsive to some changes we requested when we checked in. Is completely as advertised and would highly recommend!"
Villa Coral, brand new, spectacular outdoor area!
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Pool

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

10.0 out of 10, Exceptional, (3)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Enjoy cooking and dining in this well-equipped kitchen with a central island, oven, and ample counter space.

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

9.0 out of 10, Wonderful, (151)
"The place was spacious, very clean and beautiful!"
The price is ￥44,220
￥93,378 total
includes taxes & fees
Aug 9 - Aug 10
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Old Florida Style, wrap around porch, boat basin for dockage, open water
Relax on the waterfront with Adirondack chairs and a small dining table.

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 ￥44,220
￥102,848 total
includes taxes & fees
Aug 18 - Aug 19
Old Florida Style, wrap around porch, boat basin for dockage, open water
Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await
Fully equipped kitchen with refrigerator, oven, microwave, toaster, and sink.

Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await

9.8 out of 10, Exceptional, (18)
"Excellent stay"
Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await
DISCOUNT! Beautiful Home, Dock, Cabana Club Membership, Pool, Beach!
Relax by the serene water's edge, where a tranquil table setting awaits with wine and a view of the marina.

DISCOUNT! Beautiful Home, Dock, Cabana Club Membership, Pool, Beach!

10.0 out of 10, Exceptional, (26)
"Had a amazing time Villa was amazing , great location Everything was as stated , had no issues at all Host replied to any queries super quick Thanks again "
DISCOUNT! Beautiful Home, Dock, Cabana Club Membership, Pool, Beach!
Florida Keys Paradise Getaway | Private Beach Club Access | Spectacular Sunsets
Relax in style with two Adirondack chairs and a charming wooden table, perfect for al fresco dining or unwinding.

Florida Keys Paradise Getaway | Private Beach Club Access | Spectacular Sunsets

10.0 out of 10, Exceptional, (2)
"Great stay, great property, super comfortable.With 2 boys, the bunk beds were perfect!"
Florida Keys Paradise Getaway | Private Beach Club Access | Spectacular Sunsets
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25
Relax in this serene beachside retreat with an outdoor space featuring a wicker table and chairs.

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Beach nearby, sun loungers, beach towels

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

9.6 out of 10, Exceptional, (35)
"Beautiful place. Our stay was quiet and wonderful. Very clean and comfortable. "
The price is ￥10,507
￥40,434 total
includes taxes & fees
Aug 21 - Aug 22
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Enjoy ocean views from the spacious balcony and covered porch of this coastal retreat.

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (250)
"Home was clean and great location! Would definitely stay here again! "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Enjoy a serene beach experience with a clear ocean view, lounge chairs, and a dock for water activities.

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 ￥46,431
￥105,631 total
includes taxes & fees
Aug 7 - Aug 8
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.
Enjoy stunning marina views from this property's balcony, featuring a wicker chair and table.

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
Enjoy cooking in this well-equipped kitchen with a central island and standard appliances.

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
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
Relax by the ocean with a clear view, lounge chairs, and a curved pool surrounded by lush greenery.

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

10.0 out of 10, Exceptional, (183)
"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
Summer Openings - Last Minute Savings! Deep Water Canal, SwimSpa Pool, Kayaks!
Enjoy a tranquil beach experience with a palm tree, rocky shoreline, and clear blue sea.

Summer Openings - Last Minute Savings! Deep Water Canal, SwimSpa Pool, Kayaks!

10.0 out of 10, Exceptional, (159)
"The house was very nice. A quiet retreat for the week. We even had a chance to see a manatee in the canal. "
Summer Openings - Last Minute Savings! Deep Water Canal, SwimSpa Pool, Kayaks!
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
Relax by the pool surrounded by lush greenery and palm trees, with lounge chairs and a bar area at your fingertips.

Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!

9.6 out of 10, Exceptional, (26)
"Stayed here for 2 weeks with friends renting the other side. planned on doing more excursions but staying here with the pool, hot tub, and tiki bar, and being on the water we were content just to enjoy all the amenities! The hosts were very helpful if we had any questions. Would gladly book again."
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Relax by the pool surrounded by palm trees and lounge chairs.

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (18)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
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

Islander Resort

Islander Resort

10/10 Excellent
"Beautiful room. Easy access to beach and pool. Friendly staff. "
kendra 1-night trip
Posted 23 hours ago
Islander Resort