A waterfront with a pier, calm water, and houses with palm trees in the background.

Holiday Homes in Sugarloaf Key

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Our top choices for Sugarloaf Key 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 AU$930
includes taxes & fees
17 Aug - 18 Aug
Starlight Serenity - Hideaway w Stunning Views

2. Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
United States
Tom H.
The price is AU$877
includes taxes & fees
17 Aug - 18 Aug
Starlight Serenity - Hideaway with Stunning Views

3. The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
United States
Brian K.
The price is AU$2,355
includes taxes & fees
20 Aug - 21 Aug
The Hemingway - Beach Houses Key West

4. Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
8.0 out of 10, Very good, (2 reviews)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
United States
Samat S.
Private and Exclusive Beach Getaway

5. Fishermen's Paradise | Pool, 220' Dock & Open-Water Views

Fishermen's Paradise | Pool, 220' Dock & Open-Water Views
Big Pine Key
10.0 out of 10, Exceptional, (32 reviews)
"A beautiful house with everything you need to have a great time"
United States
David T.
The price is AU$2,211
includes taxes & fees
15 Aug - 16 Aug
Fishermen's Paradise | Pool, 220' Dock & Open-Water Views

6. Charming 3-bedroom house in Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West
Sands
8.4 out of 10, Very good, (12 reviews)
"This place was perfect for our family. Just the right distance between Marathon and Key West. Would definitely recommend it to anyone looking for a place to stay"
United States
Robert C.
The price is AU$865
includes taxes & fees
19 Aug - 20 Aug
Charming 3-bedroom house in Big Pine Key near Beach and Key West

7. Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool

Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool
Big Pine Key
10.0 out of 10, Exceptional, (5 reviews)
"Loved the pool and the porch! Only issue was the bugs on the porch at night, but we enjoyed it all day long. Also, kayaking was very calm and pleasant."
United States
Gretchen W.
The price is AU$916
includes taxes & fees
16 Aug - 17 Aug
Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool

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

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (126 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 AU$749
includes taxes & fees
10 Aug - 11 Aug
Kelly's Kabin - Adorable Private Summerland Key Cottage

9. 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, (14 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
The price is AU$915
includes taxes & fees
16 Aug - 17 Aug
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

10. Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
Cudjoe Key
9.8 out of 10, Exceptional, (23 reviews)
"Great location, beautiful rental very clean with access to the complex pool and also has a golf cart!"
United States
Michael C.
The price is AU$1,324
includes taxes & fees
23 Aug - 24 Aug
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

11. 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 AU$960
includes taxes & fees
14 Aug - 15 Aug
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

12. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (148 reviews)
"Nice property in a beautiful location. Great place to sit and enjoy the scenery and activities. "
United States
Andy D.
The price is AU$1,191
includes taxes & fees
1 Sept - 2 Sept
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

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

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
8.8 out of 10, Excellent, (10 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 AU$1,007
includes taxes & fees
14 Aug - 15 Aug
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

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

Sailfish Haven #390 - Ocean Views, 35' seawall
Cudjoe Key
9.0 out of 10, Wonderful, (7 reviews)
"It was a perfect home to stay in cudokey"
United States
Patricia H.
The price is AU$875
includes taxes & fees
31 Aug - 1 Sept
Sailfish Haven #390 - Ocean Views, 35' seawall

15. Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (56 reviews)
"We loved our stay! Prime location"
United States
Lacey C.
The price is AU$1,306
includes taxes & fees
14 Aug - 15 Aug
Post Card Point #319 - Ocean Views!

16. Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful views from the deck. The resort was quiet and peaceful. "
United States
G G.
The price is AU$1,375
includes taxes & fees
15 Aug - 16 Aug
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

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

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (110 reviews)
"Stay was great. We met the hosts and they were wonderful people."
United States
James B.
The price is AU$696
includes taxes & fees
16 Aug - 17 Aug
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

18. 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, (10 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 AU$878
includes taxes & fees
5 Aug - 6 Aug
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

19. Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is AU$963
includes taxes & fees
10 Aug - 11 Aug
Spanish Queen @Venture Out, Cudjoe Key

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

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is AU$696
includes taxes & fees
12 Aug - 13 Aug
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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 Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Sugarloaf Key Holiday Homes information

Number of reviews
566
Accommodation
897 Holiday Homes
Lowest Price
AU$696
Highest Price
AU$2,355

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