Holiday Homes in Florida Keys

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19 Sept - 21 Sept

Featured Holiday Homes in Florida Keys and around

The Hammocks at Marathon
Outdoor pool, pool umbrellas, pool loungers

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, (69)
"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, (47)
"We absolutely loved this home. High end touches throughout and all the amenities you could ever need. Wonderful communication from the host. "
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!
"Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage
Outdoor pool, a heated pool

"Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage

10.0 out of 10, Exceptional, (228)
"Quick responses from the host. Great location and home has lots to offer!"
"Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage
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
Fridge, microwave, oven, stovetop

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!"
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

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. "
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
Fridge, microwave, dishwasher, coffee/tea maker

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

9.8 out of 10, Exceptional, (17)
"Excellent stay"
Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await
Blue Island Marathon!
Exterior

Blue Island Marathon!

10.0 out of 10, Exceptional, (11)
"This gouse was an absolute gem.Will absolutely return for future vacations."
Blue Island Marathon!
DISCOUNT! Beautiful Home, Dock, Cabana Club Membership, Pool, Beach!
Outdoor dining

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
Terrace/patio

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
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, (32)
"Beautiful place. Our stay was quiet and wonderful. Very clean and comfortable. "
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Exterior

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

9.8 out of 10, Exceptional, (249)
"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
Beach nearby

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. "
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.
Terrace/patio

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.
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Outdoor pool, a heated pool

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
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (56)
"It was a beautiful home and Francine, our host, was most accommodating."
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
Terrace/patio

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

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
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

Hawks Cay Resort

Hawks Cay Resort

10/10 Excellent
"Great stay with family! Lots to do and plenty nearby for other dining and shopping options."
Cynthia 4-night trip
Posted 10 hours ago
Hawks Cay Resort