Search Vacation Homes in Sugarloaf Key

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Our top choices for Sugarloaf Key vacation homes

1. 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 ¥37,851
¥102,535 total
includes taxes & fees
Nov 19 - Nov 20
Starlight Serenity - Hideaway with Stunning Views

2. 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 ¥48,547
¥109,955 total
includes taxes & fees
Nov 19 - Nov 20
Starlight Serenity - Hideaway w Stunning Views

3. Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
United States
Harvey(Tabb) M.
Private and Exclusive Florida Keys Getaway

4. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is ¥22,639
¥66,455 total
includes taxes & fees
Nov 20 - Nov 21
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

5. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
9.0 out of 10, Wonderful, (2 reviews)
"This was a sweet little modular home that gave us a clean and comfortable place to stay… away from the tourist scene."
United States
Nora Kay F.
The price is ¥26,411
¥71,018 total
includes taxes & fees
Nov 20 - Nov 21
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

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
8.6 out of 10, Excellent, (4 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 ¥24,902
¥69,321 total
includes taxes & fees
Nov 16 - Nov 17
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

7. 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, (18 reviews)
"Perfect location, great price."
United States
Suzanne T.
The price is ¥28,676
¥73,887 total
includes taxes & fees
Nov 16 - Nov 17
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

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

SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is ¥20,603
¥64,923 total
includes taxes & fees
Nov 16 - Nov 17
SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

9. 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 ¥30,185
¥75,744 total
includes taxes & fees
Nov 16 - Nov 17
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

10. Canal-Front Retreat with Dock, Pool & Open Ocean Views

Canal-Front Retreat with Dock, Pool & Open Ocean Views
Cudjoe Key
9.0 out of 10, Wonderful, (13 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 ¥29,430
¥74,733 total
includes taxes & fees
Nov 20 - Nov 21
Canal-Front Retreat with Dock, Pool & Open Ocean Views

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

SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

12. Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Cudjoe Key
8.8 out of 10, Excellent, (3 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is ¥30,185
¥75,744 total
includes taxes & fees
Nov 16 - Nov 17
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

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

Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Cudjoe Key
9.6 out of 10, Exceptional, (7 reviews)
"Clean and excellent water access"
United States
Chris P.
The price is ¥28,676
¥73,887 total
includes taxes & fees
Nov 21 - Nov 22
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

14. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
The price is ¥33,958
¥80,148 total
includes taxes & fees
Nov 16 - Nov 17
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

15. 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, (5 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is ¥30,185
¥76,223 total
includes taxes & fees
Nov 16 - Nov 17
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

16. 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
9.6 out of 10, Exceptional, (18 reviews)
"It was great!"
United States
Jennifer B.
The price is ¥33,958
¥80,148 total
includes taxes & fees
Nov 20 - Nov 21
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

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

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (129 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is ¥30,904
¥76,393 total
includes taxes & fees
Nov 16 - Nov 17
Kelly's Kabin - Adorable Private Summerland Key Cottage

18. 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, (6 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is ¥32,448
¥78,449 total
includes taxes & fees
Nov 18 - Nov 19
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

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

Sailfish Haven #390 - Ocean Views, 35' seawall
Cudjoe Key
9.0 out of 10, Wonderful, (9 reviews)
"great House , and if you are a boater , venture out is great in cudjoe key FL"
United States
freddy c.
The price is ¥36,055
¥82,507 total
includes taxes & fees
Nov 29 - Nov 30
Sailfish Haven #390 - Ocean Views, 35' seawall

20. Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Cudjoe Key
8.8 out of 10, Excellent, (240 reviews)
"A wonderful place overlooking the water. Morning sunrises on the patio couldn't have been better. A safe, friendly community."
United States
Iva B.
The price is ¥39,928
¥77,001 total
includes taxes & fees
Nov 20 - Nov 21
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
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.

Learn more about Sugarloaf Key

Kayak through mangrove tunnels and spot colorful fish in the crystal-clear waters surrounding this laid-back island. Unwind on Sugarloaf Beach's white sands or explore Upper Sugarloaf Sound, where local boaters know the best snorkeling spots.

A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.

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