Lower Florida Keys Holiday Rentals from NZ$395: Search Short-Term Rentals

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Our top choices for Lower Florida Keys holiday rentals

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

1. Old Wooden Bridge Resort and Marina

Punta Brisa

Jordan

includes taxes & fees

4 Dec - 5 Dec

A row of floating houses with balconies, connected by walkways, on calm water.

2. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

includes taxes & fees

10 Nov - 11 Nov

A covered outdoor area with wicker furniture and string lights.

3. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Cudjoe Key

jim b.

includes taxes & fees

11 Nov - 12 Nov

A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

4. SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

Blue Mountain Footwear F.

includes taxes & fees

21 Nov - 22 Nov

A pool area with multiple swimming pools, lounge chairs, and palm trees.

5. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Cudjoe Key

Alisa M.

includes taxes & fees

10 Nov - 11 Nov

A cozy interior with a patterned sofa, a small table, and a decorative curtain.

6. 2-bedroom boat in fabulous Key West with kayaks

Stock Island

includes taxes & fees

10 Dec - 11 Dec

A marina with boats docked, a white building with a balcony, and palm trees in the background.

7. Canal Front home with easy Ocean access

Cudjoe Key

Rafael G.

includes taxes & fees

26 Nov - 27 Nov

A waterfront property with a covered porch, a boat dock, and a clear sky.

8. SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

Mckayla S.

includes taxes & fees

11 Nov - 12 Nov

A wooden deck with a large tree, outdoor seating, and a marina in the background.

9. Poolside Cottage #412

Key West

shannon b.

includes taxes & fees

1 Dec - 2 Dec

10. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Cudjoe Key

Suzanne T.

includes taxes & fees

10 Nov - 11 Nov

A resort pool area with lounge chairs and palm trees, surrounded by resort buildings.

11. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

Stock Island

Benjamin

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a sofa, coffee table, and a dining area with a table and chairs. There is a kitchen area with cabinets and appliances.

12. The Grand Cayman | Beautifully Remodeled Key West!

Key West

Matt R.

includes taxes & fees

29 Nov - 30 Nov

A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

13. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

Key West

Teri K.

includes taxes & fees

10 Nov - 11 Nov

A coastal property with a paved driveway leading to a building with a blue roof, surrounded by lush greenery and a view of the ocean.

14. Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key

Dennis G.

includes taxes & fees

14 Nov - 15 Nov

A white building with a covered porch and a palm tree.

15. Steps from Duval, Pool on Site & Bikes Included!

Old Town Key West

Laura D.

includes taxes & fees

2 Dec - 3 Dec

A hot tub with a view of a marina and boats during sunset.

16. Living the Dream Key West Style

Stock Island

Zach C.

includes taxes & fees

11 Nov - 12 Nov

A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

17. Poolside Cottage #411

Key West

Jennifer W.

includes taxes & fees

1 Dec - 2 Dec

A waterfront property with a large building, a dock with boats, and palm trees.

18. Grand Marina Suite - Poolside & Waterfront Condo

Stock Island

CAROL K.

includes taxes & fees

17 Nov - 18 Nov

A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

19. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Stock Island

Melanie K.

includes taxes & fees

10 Nov - 11 Nov

A covered outdoor deck with a sofa and table, overlooking a marina with boats and palm trees.

20. Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key

Laurie C.

includes taxes & fees

14 Nov - 15 Nov

View all properties

Find holiday rentals that suit your style

Top Lower Florida Keys Hotel Reviews

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

Almond Tree Inn Hotel - Adults Only

Old Town Key West

10/10 Excellent

Robyn

A tropical outdoor area with palm trees, hanging plants, and string lights.

Douglas House - Adults Only

Old Town Key West

10/10 Excellent

Xiaojun

A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

The Gardens Hotel

Old Town Key West

10/10 Excellent

Raf

A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

Artist House Key West

Key West Historic District

10/10 Excellent

ian

A pool area with lounge chairs and a table, surrounded by palm trees.

Orchid Key Inn - Adults Only

Old Town Key West

10/10 Excellent

Ali

An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

H2O Suites - Adults Only

Old Town Key West

8/10 Good

When fully operation, this hotel represents a really beautiful experience, but I am only able to state what occurred on my watch. My only gripe is that if you offer a turn down service, you refresh the room, take out the dirty towels and fulfil the service offerings stated on the brochure. I don't regard leaving 2 muffins wrapped in plastic as a turn down service to speak of and actually felt it ignored the greater need at the time. Also, the front desk supervisor was really fantastic but the...

Anonymous traveller

A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

Island City House Hotel

Key West Historic District

10/10 Excellent

David

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$395 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.

Lower Florida Keys Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lower Florida Keys holiday rentals

1. Old Wooden Bridge Resort and Marina

2. Aqua Lodges at Hurricane Hole Marina

3. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

4. SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

5. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

6. 2-bedroom boat in fabulous Key West with kayaks

7. Canal Front home with easy Ocean access

8. SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

9. Poolside Cottage #412

10. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

11. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

12. The Grand Cayman | Beautifully Remodeled Key West!

13. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

14. Kelly's Kabin - Adorable Private Summerland Key Cottage

15. Steps from Duval, Pool on Site & Bikes Included!

16. Living the Dream Key West Style

17. Poolside Cottage #411

18. Grand Marina Suite - Poolside & Waterfront Condo

19. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

20. Canal front, dockage, 2 bedroom, 2 bath

Find holiday rentals that suit your style

Top Lower Florida Keys Hotel Reviews

Almond Tree Inn Hotel - Adults Only

10/10 Excellent

Find out more about Lower Florida Keys

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

How to find incredible deals on Lower Florida Keys rentals

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