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 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 NZ$1,059
includes taxes & fees
27 Oct - 28 Oct
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 NZ$1,146
includes taxes & fees
27 Oct - 28 Oct
Starlight Serenity - Hideaway w Stunning Views

3. 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 NZ$765
includes taxes & fees
2 Nov - 3 Nov
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

4. 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 NZ$833
includes taxes & fees
11 Nov - 12 Nov
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is NZ$867
includes taxes & fees
16 Nov - 17 Nov
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is NZ$822
includes taxes & fees
19 Nov - 20 Nov
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is NZ$824
includes taxes & fees
29 Oct - 30 Oct
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

8. 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 NZ$824
includes taxes & fees
25 Oct - 26 Oct
Canal-Front Retreat with Dock, Pool & Open Ocean Views

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

Sailfish Haven #390 - Ocean Views, 35' seawall
Cudjoe Key
9.0 out of 10, Wonderful, (8 reviews)
"great House , and if you are a boater , venture out is great in cudjoe key FL"
United States
freddy c.
The price is NZ$938
includes taxes & fees
7 Nov - 8 Nov
Sailfish Haven #390 - Ocean Views, 35' seawall

10. 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 NZ$883
includes taxes & fees
25 Oct - 26 Oct
Kelly's Kabin - Adorable Private Summerland Key Cottage

11. 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$892
includes taxes & fees
31 Oct - 1 Nov
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

12. 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 NZ$885
includes taxes & fees
28 Oct - 29 Oct
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

13. 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$860
includes taxes & fees
28 Oct - 29 Oct
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

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$916
includes taxes & fees
25 Oct - 26 Oct
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

15. 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 NZ$914
includes taxes & fees
25 Oct - 26 Oct
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

16. 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 NZ$844
includes taxes & fees
27 Oct - 28 Oct
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

17. 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, (17 reviews)
"It was great!"
United States
Jennifer B.
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

18. Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape

Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape
Cudjoe Key
8.8 out of 10, Excellent, (3 reviews)
"Great location and accommodations "
United States
Brandie Lane c.
The price is NZ$1,121
includes taxes & fees
4 Nov - 5 Nov
Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape

19. 105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool
Cudjoe Key
105 - Newly renovated house Oceanside and Pool

20. Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (104 reviews)
"Great location plenty of room for 4 adults and 2 kids"
United States
Bob B.
The price is NZ$1,231
includes taxes & fees
26 Oct - 27 Oct
Oceanfront home-shared swimming pool, dockage-just 20 miles from 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.
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Top Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Sugarloaf Key Holiday Homes information

Number of reviews
539
Accommodation
882 Holiday Homes
Lowest Price
NZ$765
Highest Price
NZ$1,231

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