Lower Florida Keys Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Our top choices for Lower Florida Keys holiday rentals

2.5 star property
8.6 out of 10, Excellent, (283)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
Old Wooden Bridge Resort and Marina

Mobile Home in Big Pine Key

Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (160)
"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "
United States
brenda
The price is NZ$588
includes taxes & fees
4 Jan - 5 Jan 2026
Sunshine Key RV Resort & Marina

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is NZ$665
includes taxes & fees
14 Jan - 15 Jan 2026
Aqua Lodges at Hurricane Hole Marina
2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
The price is NZ$1,603
includes taxes & fees
20 Jan - 21 Jan 2026
Grand Marina Suite by Brightwild Waterfront
3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is NZ$1,759
includes taxes & fees
16 Jan - 17 Jan 2026
Atlantic View Luxury Villa with Pool

Holiday Home in Upper Sugarloaf Key

Palm - Beach Houses Key West
10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
United States
Harvey(Tabb) M.
The price is NZ$3,436
includes taxes & fees
4 Jan - 5 Jan 2026
Palm - Beach Houses Key West
9.2 out of 10, Wonderful, (142)
"Really nice location and a beautiful pool. The gym/activities area was not well equipped "
United States
Jennifer H.
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise

Holiday Home in Raccoon Key

Springtide House at Lunara Bay
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
The price is NZ$2,625
includes taxes & fees
4 Jan - 5 Jan 2026
Springtide House at Lunara Bay

Holiday Home in Raccoon Key

Capmar House at Lunara Bay
9.8 out of 10, Exceptional, (29)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is NZ$2,702
includes taxes & fees
7 Jan - 8 Jan 2026
Capmar House at Lunara Bay
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is NZ$1,045
includes taxes & fees
10 Jan - 11 Jan 2026
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is NZ$1,045
includes taxes & fees
18 Jan - 19 Jan 2026
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Condo in Old Town Key West

Rooftop Penthouse
9.8 out of 10, Exceptional, (50)
"wonderful place!!"
United States
Libby S.
The price is NZ$2,075
includes taxes & fees
3 Jan - 4 Jan 2026
Rooftop Penthouse
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is NZ$2,042
includes taxes & fees
7 Jan - 8 Jan 2026
One of the very few beach houses with a daily, rental license in the Keys.

Aparthotel in Key West

Ocean Front 2BR Residence
2.0 star property
The price is NZ$2,105
includes taxes & fees
4 Jan - 5 Jan 2026
Ocean Front 2BR Residence
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is NZ$864
includes taxes & fees
4 Jan - 5 Jan 2026
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
9.0 out of 10, Wonderful, (104)
"Very clean and beds are so comfortable. "
United States
Donny G.
The price is NZ$1,920
includes taxes & fees
26 Jan - 27 Jan 2026
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis
9.8 out of 10, Exceptional, (26)
"Bar across street wonderful they didn’t clean room staff talked to great with anything you needed court yard could have been better maintained overall would go back and stay there "
United States
Richele
The price is NZ$1,020
includes taxes & fees
9 Jan - 10 Jan 2026
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Cottage in Old Town Key West

HIDDEN OASIS 3 blocks from Duval
2.5 star property
9.6 out of 10, Exceptional, (96)
"We absolutely loved this place! It was quaint and quiet location. It was beautifully landscaped and I loved the Hidden Oasis unit and would stay there again!"
United States
Kathryn W.
The price is NZ$1,814
includes taxes & fees
17 Jan - 18 Jan 2026
HIDDEN OASIS 3 blocks from Duval
9.6 out of 10, Exceptional, (415)
"We loved it here! Not very far from Duval street. "
United States
Keghan J.
The price is NZ$641
includes taxes & fees
3 Jan - 4 Jan 2026
Steps from Duval, Pool on Site & Bikes Included!
9.8 out of 10, Exceptional, (116)
"Great location, close to everything family had a great time."
United States
rafael m.
The price is NZ$1,354
includes taxes & fees
2 Jan - 3 Jan 2026
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Lower Florida Keys Hotel Reviews

Find out more about Lower Florida Keys

Everything you need to know about Lower Florida Keys holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lower Florida Keys holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lower Florida Keys holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Lower Florida Keys holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lower Florida Keys. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lower Florida Keys holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lower Florida Keys holiday rentals we have selected for you start as low as NZ$533 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lower Florida Keys rentals

At Expedia, we put the best Lower Florida Keys holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Lower Florida Keys rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lower Florida Keys holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lower Florida Keys. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.