Lower Keys Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Lower Keys

Old Wooden Bridge Resort and Marina
Living area
Old Wooden Bridge Resort and Marina
2.5 star property
8.4 out of 10, Very good, (157)
"A cute apartment and a beautiful place, but charging 100 dollars for cleaning to a person who rented an apartment for only one night is an exaggeration in my opinion. Calculation of cost should be the ratio of their stay to the number of nights."
The price is HK$1,003
HK$1,905 total
includes taxes & fees
7 Nov - 8 Nov
Old Wooden Bridge Resort and Marina
Sunshine Key RV Resort & Marina
Sun deck
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (140)
"A great place to relax and enjoy nature, fishing opportunities, and more"
The price is HK$2,769
HK$3,115 total
includes taxes & fees
6 Dec - 7 Dec
Sunshine Key RV Resort & 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)
"the property it is good but expedia say good price for cleaning and vrbo say higher price i not agree, because i believed all time that cleaning it is the price said Expedia thanks , but i never rent or recommend again thanks"
The price is HK$2,137
HK$5,531 total
includes taxes & fees
10 Nov - 11 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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
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 HK$2,137
HK$4,702 total
includes taxes & fees
1 Dec - 2 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage
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 HK$4,656
HK$10,322 total
includes taxes & fees
10 Nov - 11 Nov
One of the very few beach houses with a daily, rental license in the 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
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
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!
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (196)
"We had a wonderful time for a quick Labor Day weekend trip. The neighborhood is family friendly and we enjoyed riding the bikes to the pool with our kids. It was convenient to have the boat ramp in the community as well. The house was clean, comfortable and well stocked. Thank you for sharing your home with us! "
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Tropical Caribbean Wonderland
Pool
Tropical Caribbean Wonderland
9.2 out of 10, Wonderful, (77)
"The camper was clean and easy to find. There’s a bath/shower house 2campsites away. We enjoyed our stay."
Tropical Caribbean Wonderland
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 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
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 HK$1,548
HK$3,867 total
includes taxes & fees
12 Nov - 13 Nov
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
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
9.8 out of 10, Exceptional, (57)
"Our family of five adults and a dog had a fantastic week at this beautiful house! We had plenty of space, it was super clean and well kept. The countertop ice maker was definitely appreciated! We didn’t cook but all the tools you could need are there. We did place an Instacart order from Publix for a few things and delivery was no problem. Lots of restaurants are within a short drive and Kiki’s right down the road was a plus and had great food. We spent most mornings and evenings hanging out on...
Old Florida Style, wrap around porch, boat basin for dockage, open water
Ocean Front Luxury Vacation Rental Near Key West
On the beach
Ocean Front Luxury Vacation Rental Near Key West
9.4 out of 10, Exceptional, (40)
"Entering the Villa was pure ‘Candy to the Eye!’ All amenities were over the top. We absolutely loved the beach, kayaks and canoes. So much fun. The pool was fabulous. The outdoor furniture was so beachy, comfy and many fun seating arrangements. Enjoyed coffee on the balcony every morning. Views, views, views, just stunning. We would love to return to the Villa in the future and stay longer!"
Ocean Front Luxury Vacation Rental Near Key West
Springs Venture Out Dolphin House (#386) with beautiful open water views
Outdoor pool, a heated pool
Springs Venture Out Dolphin House (#386) with beautiful open water views
9.4 out of 10, Exceptional, (85)
"The accommodations were well above and beyond expectations 💕 The host was easily accessible and very helpful. The place was clean and well stocked. We had an amazing time "
Springs Venture Out Dolphin House (#386) with beautiful open water views
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Sun-loungers, beach towels
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
9.6 out of 10, Exceptional, (40)
"The property was just as it was listed as, very clean and very inviting. We loved that it was so quiet! We will definitely go back again!"
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
SEA SHELL COTTAGE UNIT #2
Beach
SEA SHELL COTTAGE UNIT #2
9.2 out of 10, Wonderful, (11)
"We thoroughly enjoyed our stay here, the room we rented was perfect for us it definitely has an old school vibe. The pool was nice on the hot summer days but they were going through a bit of a crab invasion while we were there. But that was no big deal for us. Hope was super nice and have a bunch of suggestions for things to do and places to eat while down there. Ask in all we had a great time and will try to return in the future."
SEA SHELL COTTAGE UNIT #2
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
Outdoor dining
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
9.2 out of 10, Wonderful, (96)
"My family had a wonderful time staying for 10 days over mini lobster season. The location was perfect. We could walk to Kiki's Bar and Restaurant for live music and food. Gas for the boat is just across Pine Channel. Short drive to groceries, gas, pharmacy, and bait. Property manager was quick to respond. Long dock with water for the boat. My only wish was power at the end of the dock to recharge my trolling motor. Otherwise, great stay!"
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
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.
Don't see what you're looking for?
See all available properties in Lower Keys
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Lower Keys you may be interested in

Parmer's Resort
View from property
Parmer's Resort
2.5 star property
8.8 out of 10, Excellent, (1008)
"Friendly Staff, free breakfast"
The price is HK$951
HK$1,324 total
includes taxes & fees
17 Nov - 18 Nov
Parmer's Resort
Sugarloaf Key Hotel at KOA Resort
Private beach, snorkelling, kayaking, motor boating
Sugarloaf Key Hotel at KOA Resort
3.0 star property
9.8 out of 10, Exceptional, (261)
"The staff couldn't have been any nicer. We had a great time. We will be back. "
Sugarloaf Key Hotel at KOA Resort
Sugar Loaf Lodge
Balcony
Sugar Loaf Lodge
2.5 star property
8.0 out of 10, Very good, (1007)
"Nice and quiet "
The price is HK$1,081
HK$1,216 total
includes taxes & fees
24 Nov - 25 Nov
Sugar Loaf Lodge
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.