Search Holiday Homes in Lower Keys

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Browse Select Lower Keys Holiday Homes

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
9.0 out of 10, Wonderful, (66)
"Very quiet, clean, and overall great experience. I’ve been staying at properties in the Keys for over 20 years and this is one of the best experiences I have had."
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Kelly's Kabin - Adorable Private Summerland Key Cottage
Fridge, microwave, oven, stovetop
Kelly's Kabin - Adorable Private Summerland Key Cottage
9.8 out of 10, Exceptional, (103)
"Fantastic little spot to stay if you want to be away from the Key West mobs but want to be close enough for a quick trip there. Finely equipped cottage with good parking and close to a few good places to eat. Very clean and enjoyable."
The price is £477
includes taxes & fees
1 Dec - 2 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage
20 MINUTES TO KEY WEST , BOATERS PARADISE
Exterior
20 MINUTES TO KEY WEST , BOATERS PARADISE
9.6 out of 10, Exceptional, (42)
"We enjoyed our stay. The resort area itself was nice and convenient for our needs. Communication with host was excellent. Any questions were promptly answered, as well as additional info to help us in the area. The property description is accurate. We'd be pleased to stay there again."
20 MINUTES TO KEY WEST , BOATERS PARADISE
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Outdoor dining
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
9.6 out of 10, Exceptional, (79)
"The stay was good. It was close enough to wedding venue. Few things wrong when we got there. My husband fixed the closet door because it would not open n shut also a door knob was about to fall off so he tightened it."
The price is £344
includes taxes & fees
1 Nov - 2 Nov
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, (24)
"The coconut telegraph was a beautiful stilted home. It was very clean and decorated very nicely with light beachy colors. The best were very comfortable. Everything in the kitchen was functional. It was a great location. We kept our small boat at the dock The property management was very friendly. We were very happy with it and will stay there again.."
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Outdoor dining
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.0 out of 10, Wonderful, (181)
"The view was wonderful. Great place to see sunrise every morning. This was a girls trip. If you are just there for fishing, this place is perfect. The refrigerator and freezer smelled of fish. Even after 3 nights, the smell was strong. I recommend bringing some arm and hammer baking soda for both fridge and freezer. The place is pretty close to Key West, so location is great. The neighbors were cleaning their fish right off the dock, so there were many seagulls. With seagulls, comes poop. They...
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (95)
"Great property. Brought our boat and had a great time. Quick drive to Key Wedt."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Miscellaneous
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
9.8 out of 10, Exceptional, (106)
"Everything was great and Melanie was very easy to communicate with! "
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Latitudes - Ocean front with pool
Pool
Latitudes - Ocean front with pool
10.0 out of 10, Exceptional, (21)
"The house is located close to Key West avoiding the long drive to other Keys. There are excellent restaurants right on Cudjoe and great charters to do back country fishing. Bahia Honda is beautiful beach to visit which is also close by. Property has a nice pool and room to fish from the dock. Can’t go wrong with the property if you are looking for 4 bath and 4 bedrooms L."
Latitudes - Ocean front with pool
Tropical Paradise - Ocean front with swim spa
Pool
Tropical Paradise - Ocean front with swim spa
9.6 out of 10, Exceptional, (74)
"We appreciated all the extra towels for our stay as we were on the boat and in the water a couple times a day. Not really easy parking with a boat, Trailor and 3 vehicles. We were lucky no one was staying in the home adjacent that is managed by the same company. We were very happy with our stay otherwise. Florida Salts Family! "
Tropical Paradise - Ocean front with swim spa
Island Therapy
A heated pool
Island Therapy
9.8 out of 10, Exceptional, (47)
"The ice maker wasn’t working. The tray on the inside was broken. There wasn’t any dish soap. I thought it came with my stay. But overall we have stayed in this place 3 times. And Wii come back again"
Island Therapy
Amazing Open Water Views - Venture Out Unit #374
Exterior
Amazing Open Water Views - Venture Out Unit #374
10.0 out of 10, Exceptional, (11)
"Was exactly as advertises, great location, and view."
Amazing Open Water Views - Venture Out Unit #374
One of the very few beach houses with a daily, rental license in the Keys.
Outdoor pool
One of the very few beach houses with a daily, rental license in the Keys.
9.0 out of 10, Wonderful, (54)
"We stayed here with another family, so we had a total of 13 people. The view is beautiful. The pool and tiki hut and pool table are was awesome for our family to hang out. It doesn’t have any shade right by the pool but the tiki hut and pool table area were shaded. The second king bedroom is upstairs after walking up spiral staircase. There is no private door- it’s kind of like a loft. And then there’s a bunk room that is off of the king bedroom upstairs so if you want privacy, good luck. The...
The price is £1,048
includes taxes & fees
3 Nov - 4 Nov
One of the very few beach houses with a daily, rental license in the Keys.
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
Beach
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
9.8 out of 10, Exceptional, (182)
"We enjoyed our visit to Cudjoe Key. We rented a boat for two days to enjoy snorkeling. It was great being able to tie up the boat outside our rental."
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
Ocean/Canal Views 21ft Dock - Venture Out #357
Terrace/patio
Ocean/Canal Views 21ft Dock - Venture Out #357
9.0 out of 10, Wonderful, (11)
"My travel buddy and I stayed here for 5 days. Peaceful, serene, so relaxing!"
Ocean/Canal Views 21ft Dock - Venture Out #357
OCEANFront Gem! True Southern Exposure - Venture Out Unit 93
Property grounds
OCEANFront Gem! True Southern Exposure - Venture Out Unit 93
9.0 out of 10, Wonderful, (6)
"It would be nice if beach chairs, umbrella and a cooler were provided"
OCEANFront Gem! True Southern Exposure - Venture Out Unit 93
Dickey's Dockside Retreat
Fridge, microwave, oven, stovetop
Dickey's Dockside Retreat
10.0 out of 10, Exceptional, (1)
"What a way to check out of the weather up north and check into paradise - that's exactly what we did. We'll be back next year."
Dickey's Dockside Retreat
Fun in the Sun in Cudjoe Key! #51
Exterior
Fun in the Sun in Cudjoe Key! #51
2.0 star property
8.0 out of 10, Very good, (2)
"Great property unbelievable views would definitely come back"
Fun in the Sun in Cudjoe Key! #51
Brand New Home on The Ocean, bring your boat and RV!!
Property grounds
Brand New Home on The Ocean, bring your boat and RV!!
10.0 out of 10, Exceptional, (2)
"House was on the canal. Beautiful sunrises. House was clean and well equipped. Convenient to Key West and state park. Enjoyed our stay. Host was very friendly and helpful. Would stay here again"
Brand New Home on The Ocean, bring your boat and RV!!
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun-loungers, beach towels
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (215)
"it was peaceful and nice. "
The price is £566
includes taxes & fees
1 Nov - 2 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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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Other property types in Lower Keys

Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV
Old Wooden Bridge Resort and Marina
2.5 star property
8.4 out of 10, Very good, (155)
"Very nice accommodations and staff."
The price is £189
includes taxes & fees
4 Nov - 5 Nov
Old Wooden Bridge Resort and Marina
34’ Catamaran Sailboat
Interior
34’ Catamaran Sailboat
9.6 out of 10, Exceptional, (27)
"Overall it was a great experience."
34’ Catamaran Sailboat
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun-loungers, beach towels
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (215)
"it was peaceful and nice. "
The price is £566
includes taxes & fees
1 Nov - 2 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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.