A coastal landscape with clear turquoise waters, a long bridge, and a small island with buildings.

Holiday Homes in Lower Florida Keys

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Our top choices for Lower Florida Keys holiday homes

1. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is NZ$985
includes taxes & fees
30 Sept - 1 Oct
Starlight Serenity - Hideaway w Stunning Views

2. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (111 reviews)
"$125.00 extra charge when arriving. Almost all the remotes needed batteries. Furniture was all shoved up against walls, everything needed to be set back up. Kayaks were under house buried under a massive amount of junk and covered with sand and debris. A/C worked on and off. A/c window unit drain poured water on steps down to sea wall making them very slippery all the time. May have been a very nice place years ago but really shows its age and poor maintenance. Did not feel like calling the...
United States
Ken
The price is NZ$687
includes taxes & fees
2 Sept - 3 Sept
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (128 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
The price is NZ$846
includes taxes & fees
2 Sept - 3 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage

4. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
The price is NZ$972
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

5. Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!

Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
Old Town Key West
9.0 out of 10, Wonderful, (199 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!

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

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.0 out of 10, Very good, (3 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is NZ$962
includes taxes & fees
2 Sept - 3 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

7. SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is NZ$730
includes taxes & fees
2 Sept - 3 Sept
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

8. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (69 reviews)
"We stayed here for our honeymoon and it was perfect. The place was clean and well appointed. The pool right outside was huge and we spent lots of time there. Highly recommend!"
United States
DeAnna Z.
The price is NZ$513
includes taxes & fees
7 Sept - 8 Sept
Poolside Cottage #411

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

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.4 out of 10, Exceptional, (17 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is NZ$1,017
includes taxes & fees
2 Sept - 3 Sept
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

10. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.6 out of 10, Exceptional, (4 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is NZ$1,040
includes taxes & fees
2 Sept - 3 Sept
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

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

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (11 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
The price is NZ$1,040
includes taxes & fees
2 Sept - 3 Sept
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

12. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (36 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is NZ$542
includes taxes & fees
15 Sept - 16 Sept
Poolside Cottage #412

13. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (38 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is NZ$1,103
includes taxes & fees
7 Sept - 8 Sept
Paradise found

14. Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is NZ$1,063
includes taxes & fees
6 Sept - 7 Sept
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

15. Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Cudjoe Key
9.4 out of 10, Exceptional, (6 reviews)
"Clean and excellent water access"
United States
Chris P.
The price is NZ$1,017
includes taxes & fees
3 Sept - 4 Sept
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

16. Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
9.0 out of 10, Wonderful, (11 reviews)
"This property is convenient to food and fun. It was very clean, comfortable and we felt safe to walk around the resort. We had a wonderful stay here."
United States
Catherine C.
The price is NZ$1,058
includes taxes & fees
13 Sept - 14 Sept
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

17. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (23 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is NZ$753
includes taxes & fees
2 Sept - 3 Sept
Road's End | Prime Old Town Location! Updated Home w/ Pool

18. Sailfish Haven #390 - Ocean Views, 35' seawall

Sailfish Haven #390 - Ocean Views, 35' seawall
Cudjoe Key
9.0 out of 10, Wonderful, (8 reviews)
"It was a perfect home to stay in cudokey"
United States
Patricia H.
The price is NZ$1,050
includes taxes & fees
2 Sept - 3 Sept
Sailfish Haven #390 - Ocean Views, 35' seawall

19. Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
8.0 out of 10, Very good, (21 reviews)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is NZ$839
includes taxes & fees
12 Sept - 13 Sept
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

20. Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Cudjoe Key
9.4 out of 10, Exceptional, (15 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
The price is NZ$1,073
includes taxes & fees
10 Sept - 11 Sept
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
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.
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Top Lower Florida Keys Hotel Reviews

Find out more about Lower Florida Keys

Lower Florida Keys Holiday Homes information

Number of reviews
558
Accommodation
884 Holiday Homes
Lowest Price
NZ$513
Highest Price
NZ$1,103

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