Holiday Homes in Lower Keys

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Lower Keys

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, (86)
"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$1,082
includes taxes & fees
25 Aug - 26 Aug
Oceanfront home-shared swimming pool, dockage-just 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)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
Smart TV

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

9.8 out of 10, Exceptional, (73)
"We loved the spacious home with pool and little fishing dock. The kayaks were fun too. It was roughly 30 minutes to key west and the same to marathon key. Would definitely stay again."
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
A heated pool

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$1,289
includes taxes & fees
23 Aug - 24 Aug
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys 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
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Outdoor pool, a heated pool

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."
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
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
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Beach nearby, sun-loungers, beach towels

Mini lobster available! Open Water View from porch , dock, bikes, kayaks

9.8 out of 10, Exceptional, (121)
"We loved having our own space for a boat. Great location."
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Outdoor dining

Cudjoe Cottages, swimming pool, just 20 miles from Key West

8.8 out of 10, Excellent, (145)
"Near to Key West in a quiet neighborhood. "
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Sea La Vie #197 - Oceanfront, Big Boats Welcome Here!
A heated pool

Sea La Vie #197 - Oceanfront, Big Boats Welcome Here!

2.5 star property
10.0 out of 10, Exceptional, (5)
"Our stay was wonderful! The view is amazing, the home was clean and very well stocked. We had a wonderful time."
Sea La Vie #197 - Oceanfront, Big Boats Welcome Here!
Amazing Pool & Canal Ground Level Home, Ocean access
Outdoor pool, a heated pool

Amazing Pool & Canal Ground Level Home, Ocean access

9.8 out of 10, Exceptional, (19)
"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
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
A heated pool

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$935
includes taxes & fees
23 Aug - 24 Aug
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Lower Keys paradise
Outdoor pool, a heated pool

Lower Keys paradise

10.0 out of 10, Exceptional, (35)
"The property was very clean and comfortable. We had a great stay "
Lower Keys paradise
20 MINUTES TO KEY WEST , BOATERS PARADISE
Exterior

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.4 out of 10, Exceptional, (58)
"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
Waterfront 4 bed/bath West Indies Cozy Home
Terrace/patio

Waterfront 4 bed/bath West Indies Cozy Home

Waterfront 4 bed/bath West Indies Cozy Home
Newly renovated cozy and spacious beach house with breathtaking ocean front
Marina

Newly renovated cozy and spacious beach house with breathtaking ocean front

10.0 out of 10, Exceptional, (11)
"Leave the city behind and enjoy all the Florida Keys have to offer."
Newly renovated cozy and spacious beach house with breathtaking ocean front
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
On the beach, beach towels

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (237)
"Clean and inviting property, great location, attentive host. Highly recommend."
The price is AU$1,285
includes taxes & fees
23 Aug - 24 Aug
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Exterior detail

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

10.0 out of 10, Exceptional, (1)
"We just needed a place to sleep for a few days while visiting friends on Big Pine. The house had what we needed. The home and furnishings were quite dated with some rust stains on the air vents and in the bath but if you're not picky about that, then this is a great place. The main areas were clean, although there was dirt and dust behind the night stands (needed to access the outlet so had to look there). We didn't use any of the amenities but still had to pay 130 extra when we checked in at...
The price is AU$696
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Waterfront Haven House with Boat Basin & Ramp!
Sun-loungers, beach towels

Waterfront Haven House with Boat Basin & Ramp!

9.8 out of 10, Exceptional, (16)
"Beautiful place, quiet"
Waterfront Haven House with Boat Basin & Ramp!
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Marina

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

10.0 out of 10, Exceptional, (227)
"Perfect house for a few guys to stay at"
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
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 Lower Keys Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Great sleep"
Nate 1-night trip
Posted 2 days ago
Sugar Loaf Lodge