Lower Florida Keys Holiday Rentals

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Holiday Rentals in Lower Florida Keys

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, (47)
"So glad we found this location. Nice and peaceful but close to anything we needed. Sitting on the porch was so relaxing, watching boats go by. The house was very comfortable. Only wish the 2nd bedroom had a working TV. Our host was quick to answer any issue we had and left some great suggestions on places to eat. I would definitely return to enjoy this beautiful location"
Old Florida Style, wrap around porch, boat basin for dockage, open water
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, (187)
"All amenities were operational and organized. check in/check out process was easy. i thoroughly enjoyed my stay with friends. thanks"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (204)
"Beautiful and quiet location. Close to Key West yet just far enough to be away from the crowds. Family thoroughly enjoyed it. Everything is as pictured and immaculately clean, truly a gem. Melanie was friendly, always available and always responsive."
The price is NZ$717
includes taxes & fees
18 Jun - 19 Jun
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (54)
"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
34’ Catamaran Sailboat
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
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, (90)
"Explain to people that there is an opportunity to park the truck with a trailer and that there are ramps for the boat because I myself did not take my boat thinking that there was nothing like that. Thanks "
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Waterfront Home
Exterior
Waterfront Home
8.8 out of 10, Excellent, (141)
"Would definitely come back!!!!"
Waterfront Home
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
Sun-loungers, beach towels
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
10.0 out of 10, Exceptional, (26)
"Very comfortable low key rental. The house was clean and setup perfectly for what we needed. The pool was very warm more like an oversized hot tub but it was still nice to hang out in after a day out. Loved the outdoor shower! Will definitely keep this on our list of places to stay for our next trip down!"
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
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, (39)
"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."
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
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
One of the very few beach houses with a daily, rental license in the Keys.
Exterior
One of the very few beach houses with a daily, rental license in the Keys.
9.0 out of 10, Wonderful, (48)
"Great place in an unbelievable location. Nice and clean with all the amenities we needed."
The price is NZ$2,145
includes taxes & fees
28 Jun - 29 Jun
One of the very few beach houses with a daily, rental license in the Keys.
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (65)
"Resorts was great love the pool and water....home was clean nice bedrooms and baths really small but we just sleep in them. Deck was great. To be in early morning watching sun rise..."
Canal front, dockage, 2 bedroom, 2 bath
Cozy, Perfect Conch Cottage!
Pool
Cozy, Perfect Conch Cottage!
9.0 out of 10, Wonderful, (30)
"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!
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Property grounds
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
10.0 out of 10, Exceptional, (197)
"One of the best locations to stay in the Florida keys , if u have a boat and you do fishing you will appreciate it even more , i will definitely come back"
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
SEA SHELL COTTAGE UNIT #2
Beach
SEA SHELL COTTAGE UNIT #2
9.4 out of 10, Exceptional, (8)
"If you don’t need a water view this compound is perfect for what I needed. Very well maintained grounds with brick pavers on all driveways and courtyards. I stayed in a one bedroom with kitchenette with ample areas for my small boat. I will be back."
SEA SHELL COTTAGE UNIT #2
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
9.2 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
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
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.
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, (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
**KEYSIE DOES IT @ CUDJOE KEY** Private Home in Waterfront Community + LAST KEY
Property grounds
**KEYSIE DOES IT @ CUDJOE KEY** Private Home in Waterfront Community + LAST KEY
10.0 out of 10, Exceptional, (4)
"This cute home was the perfect spot for our 3 day stay in the lower keys. The place was so clean and had an excellent supply of towels, tp, and other supplies. The furniture was comfortable . The beds were ok- a little “bouncy” but that didn’t prevent us from getting a good nights rest. The small pool was a great place to relax after a day of sightseeing. We didn’t make use of kayaks or grill or table at ground level. The water hose provided was an awesome addition to clean our beach gear. This...
**KEYSIE DOES IT @ CUDJOE KEY** Private Home in Waterfront Community + LAST KEY
Comfortable Waterfront Vacation Rental
Sun-loungers, beach towels
Comfortable Waterfront Vacation Rental
9.4 out of 10, Exceptional, (139)
"Lynn was an excellent host. Very quick to respond to any questions you may have. The check in process with the resort leaves a lot to be desired. Security is not friendly nor very helpful. The neighbors we interacted with were very friendly. "
Comfortable Waterfront Vacation Rental
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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

Sugarloaf Key Hotel at KOA Resort
Private beach, snorkelling, kayaking, motor boating
Sugarloaf Key Hotel at KOA Resort
2.0 star property
9.8 out of 10, Exceptional, (163)
"Great location, spacious suite, very clean, would stay here again"
Sugarloaf Key Hotel at KOA Resort
Parmer's Resort
View from property
Parmer's Resort
2.5 star property
8.8 out of 10, Excellent, (1002)
"The people are very nice and the view was beautiful. We had a waterfront room. The onky issue is the bathroom is very outdated and the grout/shower shows it. I can look past it because its clean but others may not."
The price is NZ$342
includes taxes & fees
23 Jun - 24 Jun
Parmer's Resort
Sugar Loaf Lodge
Balcony
Sugar Loaf Lodge
2.5 star property
8.0 out of 10, Very good, (1006)
"Good 👍 "
The price is NZ$307
includes taxes & fees
6 Jun - 7 Jun
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

Looe Key Reef Resort

Looe Key Reef Resort

5/5 Excellent
"Great place for the price."
A verified traveller stayed at Looe Key Reef Resort
Posted 4 days ago
Looe Key Reef Resort