Florida Keys Holiday Rentals

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Holiday Rentals in Florida Keys

Outdoor pool, pool loungers
Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1093)
"Remodeled and very nice. Just wish our balcony overlooked the water and nit a torn up parking lot. Room was great and staff was very friendly. Breakfast was very good "
The price is NZ$481
includes taxes & fees
28 May - 29 May
Skipjack Resort & Marina
Exterior
Breezy Palms Resort
2.5 star property
8.4 out of 10, Very good, (324)
"Lovely place . Very clean . Perfect to relax "
The price is NZ$342
includes taxes & fees
27 May - 28 May
Breezy Palms Resort
Front of property
Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, (103)
"highly recommended, very clean ,pace full and nice place "
The price is NZ$533
includes taxes & fees
27 May - 28 May
Aqua Lodge Rentals At Coconut Cay
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Superior Bungalow, Ensuite (Cottage 04) | Exterior
Tropical Cottages
3.0 star property
8.4 out of 10, Very good, (684)
"Weather was prefect. There’s a lot of bugs and cottage 9 does NOT have a stove. Most street noise but nothing to loud "
The price is NZ$219
includes taxes & fees
11 Jun - 12 Jun
Tropical Cottages
2 Bedroom Aqua Lodge # 13 Barracuda | Living area
Old Wooden Bridge Resort and Marina
2.5 star property
8.4 out of 10, Very good, (122)
"Amazing stay in a boat!"
The price is NZ$420
includes taxes & fees
27 May - 28 May
Old Wooden Bridge Resort and Marina
Outdoor pool, pool loungers
Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1028)
"Wonderful location, next to 7 miles bridge and a look out see restaurant. "
The price is NZ$253
includes taxes & fees
27 May - 28 May
Knight's Key Suites
Standard Bungalow | Living area
Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, (47)
"The house boat was beautiful, clean and the patio over looking the lagoon was very relaxing. There are manatees that visit too. :) The neighbors are very friendly, as is the staff. The kayaks and bicycles are included in the rental, which is fantastic. The location s very close to groceries and local parks. We took an airplane scenic ride which was the highlight of the trip. The small airport is only 3 miles away. We will come back to Yacth Haven !"
The price is NZ$464
includes taxes & fees
6 Jun - 7 Jun
Yacht Haven Marina
Sundeck
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (130)
"Nice place, very clean and quiet. The chair and sofa bed was peeling and the kitchen ledge is uneven so we almost fell."
Sunshine Key RV Resort & Marina
Manatee: Luxury Bungalow, 4 Bedrooms, Bay View | Beach/ocean view
Mangrove Marina and Resort Aqualodge Houseboats
3.0 star property
9.4 out of 10, Exceptional, (315)
"Absolutely beautiful! Cant wait to come back and stay here again."
Mangrove Marina and Resort Aqualodge Houseboats
Exclusive Cabin | Living area
Cabins at Bonefish Bay
3.0 star property
10.0 out of 10, Exceptional, (9)
"Our group arrived not knowing what to expect after a long days travel, as soon as we pulled into the office to get our keys we were amazed at quaint cabin that awaited us. It was super easy to get the keys after hours. The cabin itself was perfect!!!! Plenty of room for a group of 5. The towels provided were perfect for the relaxing pool area. Every thing we would need for cooking was already in the cabin. The rooms were clean and bright with natural wood. The area was quiet and very well...
Cabins at Bonefish Bay
Fishing
Anchorage Resort & Yacht Club
3.0 star property
8.6 out of 10, Excellent, (262)
"Very nice and quaint property with a very relaxing charm! We definitely recommend ❤️"
The price is NZ$359
includes taxes & fees
28 May - 29 May
Anchorage Resort & Yacht Club
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
Beach
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
9.8 out of 10, Exceptional, (23)
"We loved the beautiful and quiet location of our unit within the facility and also enjoyed all of the amenities. Having the living quarters downstairs and bedrooms on the second story made it easy to accommodate early and late risers. If you like to do your own cooking, you may want to think about bringing measuring cups and perhaps ziplock baggies or wrap for any leftovers. The cupboards were stocked with some nice spices and other surprises. We had a lovely time and would definitely consider...
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Property grounds
VOTED BEST KEY LARGO VACATION RENTAL
10.0 out of 10, Exceptional, (59)
"My family and I had a fantastic visit. The Home was very clean and the property was beautiful."
VOTED BEST KEY LARGO VACATION RENTAL
Property grounds
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
9.6 out of 10, Exceptional, (115)
"The condo was very clean, well equipped and in a quiet peaceful setting.The owner was very friendly and helpful."
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Sun-loungers, beach towels
Kawama Yacht Club - 2 Bedrooms with a Private Ocean Front Beach
9.8 out of 10, Exceptional, (104)
"This was a very nice place and Jorge was great to work with."
Kawama Yacht Club - 2 Bedrooms with a Private Ocean Front Beach
Fridge, microwave, oven, stovetop
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
9.6 out of 10, Exceptional, (29)
"Everything was accurate and it was very nice and quiet!"
The price is NZ$776
includes taxes & fees
17 Jun - 18 Jun
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Beach
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
10.0 out of 10, Exceptional, (161)
"This place was exactly what we needed to get everything ready for our son’s wedding. We loved the kitchen for all of the desserts we made. It was nice to be so close to the pool. There was so much space to spread out. It’s a wonderful place to stay."
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
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$727
includes taxes & fees
29 May - 30 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
A heated pool
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
8.8 out of 10, Excellent, (205)
"My wife and our friends wanted to come down and explore the Keys. So many other Vrbo options were so expensive but luckily we found this listing on Duck Key. It is basically in the middle of the Keys section off the highway and it provided such an easy way of exploring the various Keys without feeling like we were in the car the whole time. We loved unwinding in the personal pool on the patio after a nice day of exploring along with having some of the most beautiful sunrises and sunsets that we...
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
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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 Florida Keys you may be interested in

Private beach, sun-loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1006)
"Rooms are very quiet. We had two small children and we were worried we would hear neighbors or we would bother them but you couldn’t hear anything in next room. Hotel was fully book3d "
The price is NZ$698
includes taxes & fees
27 May - 28 May
Cheeca Lodge & Spa
5 outdoor pools, pool cabanas (surcharge), pool umbrellas
Hawks Cay Resort
4.0 star property
8.0 out of 10, Very good, (1003)
"Beautiful and convenient "
The price is NZ$680
includes taxes & fees
2 Jun - 3 Jun
Hawks Cay Resort
32-inch LCD TV with satellite channels, TV, iPod dock
Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
8.8 out of 10, Excellent, (1003)
"Property was in great shape. Beach was fantastic for that area entire staff was friendly, professional, and helpful."
The price is NZ$754
includes taxes & fees
6 Jun - 7 Jun
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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 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 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 Florida Keys. Seeing all the best attractions is bound to make you fall in love with 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 Florida Keys short-term rentals, that won’t be hard to do.

Recent reviews of Florida Keys properties
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