Lower Florida Keys Holiday Rentals

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Holiday Rentals in Lower Florida Keys

Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (89)
"Good place. 3 bed rooms all with Queen size beds. It was perfect for us. We sat on the porch mostly when we were there and played games. Not a long ride to Key West. Overall- we were happy and would stay there again."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, (45)
"We brought a boat with us. The protected bay is perfect with a marked channel (note it is a tight turn to get in during high winds with shallow spots). Plenty of room for a trailer. The view here is very peaceful and we loved sitting out on the break-wall. We all slept comfortable and appreciated that each room had their own AC unit for control. The restaurant that is walking distance had great food, drinks, and live music. Minor thing, but my group wanted it passed along that the toaster needs...
Old Florida Style, wrap around porch, boat basin for dockage, open water
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (185)
"Highly recommend"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (25)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
Fridge, microwave, oven, stovetop
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (53)
"It was a nice Key West cottage with beautiful views of Cudjoe Bay."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Pool
Cozy, Perfect Conch Cottage!
9.2 out of 10, Wonderful, (29)
"Our stay was great! The description is accurate. We enjoyed our 6 Mid-March days at "Cozy Perfect Conch Cottage." Yes, it's technically camping, but it's very NICE camping...in a campground...but a very NICE campground. The bed we used (there were only 2 of us) was super comfortable. The WiFi worked great. It was awesome having a full kitchen and washer/dryer. The towels were plentiful, soft and luxurious. Linens were also very soft and comfortable. Everything needed for basic cooking was...
Cozy, Perfect Conch Cottage!
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (203)
"Overall, a very nice property in a good location, with good amenities. Located near several good Restaurants, especially the Square Grouper. Communication with Host was very good."
The price is NZ$725
per night
30 May - 31 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Exterior
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (217)
"My daughter and I stayed in Cudjoe Key to be close to Key West. The location was good. The unit had everything we needed both inside and out. We grilled and cooked which was great. The beds were comfortable. Unfortunately, the weather did not cooperate and excursions were cancelled so we spent more time in Key West than we had planned. But the unit had lots of games and the TV had the tennis channel which was very nice. All in all, it was a good time."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Exterior
One of the very few beach houses with a daily, rental license in the Keys.
9.0 out of 10, Wonderful, (48)
"Layout of house and location are perfect. The owners were very communicative and responsive."
The price is NZ$2,170
per night
28 May - 29 May
One of the very few beach houses with a daily, rental license in the Keys.
Sun-loungers, beach towels
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
10.0 out of 10, Exceptional, (25)
"Easy from start to finish! Lovely cottage in very central location in the Florida Keys. Hope was the highlight of the trip, truly the “hostess with the mostest.” She checked in daily, offered great tips for restaurants and activities. Loved everything about the property: quiet, the outdoor shower, the beds, the pool, Lulu, and the freshest seafood! Would definitely recommend."
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
A heated pool
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
10.0 out of 10, Exceptional, (14)
"Excellent concept. Loved this unit. Very clean. Only had one small glitch when checking in because I don't text. The lady who manages the unit was exceptional. Wished I could find employees like her."
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
Outdoor pool, a heated pool
Springs Venture Out Dolphin House (#386) with beautiful open water views
9.4 out of 10, Exceptional, (80)
"The location was great, right on the water with a great view. The house and amenities were perfect for us."
Springs Venture Out Dolphin House (#386) with beautiful open water views
Exterior
Waterfront Home
8.8 out of 10, Excellent, (141)
"Would definitely come back!!!!"
Waterfront Home
A heated pool
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
9.6 out of 10, Exceptional, (168)
"Property and property owner were great. Nice quiet place for relaxation."
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Beach
Enjoy Caribbean weather. Last minute opening beginning 5/19/24! Enjoy the Keys!
9.4 out of 10, Exceptional, (124)
"Great stay. Comfy beds. Everything you need."
Enjoy Caribbean weather. Last minute opening beginning 5/19/24! Enjoy the Keys!
Beach
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
9.8 out of 10, Exceptional, (168)
"We had a awesome family time there, everything is pretty and cute. We fishing behind the house, funny time. Everything was perfect to me and my family. Thank you!"
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
Outdoor dining
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
9.6 out of 10, Exceptional, (73)
"We always enjoy staying at venture out. They have everything you need right on the premises. Janet’s house was perfect for myself and three kids. Right on the canal so the kids could fish and even had a manatee come right up to us. We will definitely be back."
The price is NZ$816
per night
3 Jun - 4 Jun
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Outdoor dining
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.2 out of 10, Wonderful, (175)
"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
Property grounds
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
10.0 out of 10, Exceptional, (9)
"Perfect size for a couple. New and clean, couldn’t be happier, thanks!"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Property grounds
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
9.2 out of 10, Wonderful, (90)
"Location and outdoor living space was awesome!"
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
Don't see what you're looking for?
See all available properties in Lower Florida Keys
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.

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

Private beach, snorkelling, kayaking, motor boating
Sugarloaf Key Hotel at KOA Resort
2.0 star property
9.8 out of 10, Exceptional, (153)
"Stayed for a business trip and it was clean, comfortable, the staff is very friendly, a beautiful unit with a big balcony to relax and have a nice breakfast, lunch, or dinner, with comfy chairs and spacious table. The bathroom was updated as well as the whole unit. Very big and clean! We took our fur babies and there is a cute park for them to just roam around, or do some obstacle courses. Very clean and convenient. There is also a big heated pool with a jacuzzi, live music and a...
Sugarloaf Key Hotel at KOA Resort
View from property
Parmer's Resort
2.5 star property
8.8 out of 10, Excellent, (1002)
"Clean and tidy, good facilities, lovely beach area and views."
The price is NZ$293
per night
2 Jun - 3 Jun
Parmer's Resort
Balcony
Sugar Loaf Lodge
2.5 star property
8.0 out of 10, Very good, (1004)
"Very nice place to stay, only about 30 minutes from Key West. Nice view from the balcony. And my favorite part? Nearly instant hot water in the shower!"
The price is NZ$311
per night
28 May - 29 May
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Lower Florida Keys holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Lower Florida Keys. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Lower Florida Keys. Seeing all the best attractions is bound to make you fall in love with Lower Florida Keys. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Lower Florida Keys short-term rentals, that won’t be hard to do.

Recent reviews of Lower Florida Keys properties
Expedia verified reviews

THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4

THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4

5/5 Excellent
Beautiful Property in Great Location
"Ww stayed for 6 nights as our first time in the Keys. The property is very well manicured with everything you'll need. We had a small issue with one cottage that was quickly rectified by the owners. Hope Nd Glenn were terrific! Not sure if we'll ever return to the Keys, but we highly recommend The Hidden Hammick to anyone visiting the area."
A verified traveller stayed at THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Posted 3 days ago
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4