Holiday Homes in Lower Keys

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Lower Keys

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 AU$1,082
includes taxes & fees
18 Aug - 19 Aug
Old Florida Style, wrap around porch, boat basin for dockage, open water
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 AU$1,130
includes taxes & fees
17 Aug - 18 Aug
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
Relax in this stylish living room with a sofa, TV, and sliding glass door leading to a patio area.

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!
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
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 AU$937
includes taxes & fees
10 Aug - 11 Aug
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
20 MINUTES TO KEY WEST , BOATERS PARADISE
Enjoy waterfront views and access to a marina from this coastal property.

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.4 out of 10, Exceptional, (57)
"Great little spot, location was perfect, house was cozy, and the host was fantastic! The staff at Venture Out were also extremely courteous. Would definitely stay here again. "
20 MINUTES TO KEY WEST , BOATERS PARADISE
Private Secluded Ocean View & Pool Near Key West
Outdoor pool, a heated pool

Private Secluded Ocean View & Pool Near Key West

8.2 out of 10, Very good, (93)
"Everything was exactly as described, the host was gracious and communicative, the house is great for a large group and a quiet location"
Private Secluded Ocean View & Pool Near Key West
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Relax by the pool surrounded by palm trees and lounge chairs.

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

9.8 out of 10, Exceptional, (8)
"Beautiful place!"
The price is AU$1,272
includes taxes & fees
22 Aug - 23 Aug
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Island Time #110 Ocean Views - Cudjoe Key
Relax by the pool surrounded by palm trees and lounge chairs, with a clear view of the sea.

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (7)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
The price is AU$963
includes taxes & fees
19 Aug - 20 Aug
Island Time #110 Ocean Views - Cudjoe Key
Amazing Pool & Canal Ground Level Home, Ocean access
Relax by the pool surrounded by palm trees and lounge chairs.

Amazing Pool & Canal Ground Level Home, Ocean access

9.8 out of 10, Exceptional, (17)
"Property was fantastic, instant communication with the owner. I would highly recommend and will stay here again on our next trip to the keys. 5 stars all the way."
Amazing Pool & Canal Ground Level Home, Ocean access
Waterfront Anchor House with Boat Basin & Ramp!
Escape to a tranquil coastal haven with access to a sandy beach and lush palm trees.

Waterfront Anchor House with Boat Basin & Ramp!

9.8 out of 10, Exceptional, (18)
"Our stay was perfect. The only complain was that we couldn’t stay longer. Walt gave us a great overview of the property available amenities. The short walk to Kiki’s Sandbar makes the stay extra enjoyable. Little Torch Key is the perfect spot to avoid the hustle and bustle of Key West, but remains convenient to all of the Keys activities. "
Waterfront Anchor House with Boat Basin & Ramp!
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Relax by the pool surrounded by palm trees and a sandy deck.

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is AU$917
includes taxes & fees
17 Aug - 18 Aug
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Private and Exclusive Florida Keys Getaway
Relax by the clear blue pool surrounded by lush greenery and palm trees, integrated with natural rock formations.

Private and Exclusive Florida Keys Getaway

10.0 out of 10, Exceptional, (12)
"We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!"
Private and Exclusive Florida Keys Getaway
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Relax by the pool surrounded by palm trees and lounge chairs.

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

7.8 out of 10, Good, (12)
"Good experience. The property is well place and the Venture is really nice and quiet."
The price is AU$560
includes taxes & fees
10 Aug - 11 Aug
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Lower Keys paradise
Relax by the oceanfront pool surrounded by lounge chairs and palm trees.

Lower Keys paradise

10.0 out of 10, Exceptional, (34)
"The property was very clean and comfortable. We had a great stay "
Lower Keys paradise
Newly renovated cozy and spacious beach house with breathtaking ocean front
Enjoy waterfront views from the dock, where a small boat is moored and a covered seating area invites relaxation.

Newly renovated cozy and spacious beach house with breathtaking ocean front

10.0 out of 10, Exceptional, (11)
"I stayed at this property with my brother and mom. We all loved this house. Several key deer and an iguana frequented the property. Great location and close to everything we wanted to do. We were all sad to see that it’s not available to stay at again next year. "
Newly renovated cozy and spacious beach house with breathtaking ocean front
Ocean View 4/2 Estate with Private Pool 15 minutes from Key West
Terrace/patio

Ocean View 4/2 Estate with Private Pool 15 minutes from Key West

Ocean View 4/2 Estate with Private Pool 15 minutes from Key West
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Guests can enjoy a serene waterfront experience from this tranquil dock surrounded by lush greenery.

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very good, (114)
"Deer in the front yard, perfect location, clean and friendly "
The price is AU$836
includes taxes & fees
14 Aug - 15 Aug
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
A Tropical Luxury Getaway, Your own private resort!!
Relax by the serene pool surrounded by lush palm trees.

A Tropical Luxury Getaway, Your own private resort!!

10.0 out of 10, Exceptional, (38)
"The house and pool were very nice."
A Tropical Luxury Getaway, Your own private resort!!
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Enjoy a serene beachside setting with picnic tables arranged around a central rock mound, surrounded by palm trees and a stunning ocean view.

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (96)
"Really great, friendly community with lots of activities and a great view of the beach. Would definitely be on my list for another visit soon."
The price is AU$678
includes taxes & fees
14 Aug - 15 Aug
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
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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