Summerland Key Residences

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Recommended hotels in Summerland Key

1. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very good, (1,000 reviews)
"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."
United States
Mariia
$99 nightly
The price is $111
Nov 30 - Dec 1
Total with taxes and fees
Sugar Loaf Lodge

2. Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,001 reviews)
"Super cute place and nice people! Would definitely stay again."
United States
Natalie
$198 nightly
The price is $223
Nov 18 - Nov 19
Total with taxes and fees
Parmer's Resort

3. Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
Summerland Key
7.8 out of 10, Good, (1,000 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
$161 nightly
The price is $181
Nov 9 - Nov 10
Total with taxes and fees
Looe Key Reef Resort

4. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"This property was meticulously clean and perfect for us. The property was decorated well-very home-like feel. The communication with the host was prompt and they answered all questions asked. In addition, we loved that we could bring our fur-babies (dogs) to the property with us. We highly recommend this property!"
United States
Elena S.
$342 nightly
The price is $382
Nov 5 - Nov 6
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

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

SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
$443 nightly
The price is $492
Nov 21 - Nov 22
Total with taxes and fees
SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

6. 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.
$399 nightly
The price is $446
Nov 5 - Nov 6
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

7. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
$449 nightly
The price is $501
Nov 13 - Nov 14
Total with taxes and fees
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

8. 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.
$374 nightly
The price is $417
Nov 10 - Nov 11
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

9. 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.
$425 nightly
The price is $474
Nov 9 - Nov 10
Total with taxes and fees
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

10. Breezy Point - Venture Out Unit 199

Breezy Point - Venture Out Unit 199
Cudjoe Key
Breezy Point - Venture Out Unit 199

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

SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
$388 nightly
The price is $431
Nov 9 - Nov 10
Total with taxes and fees
SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

12. 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.
$389 nightly
The price is $434
Nov 11 - Nov 12
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

13. 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.
$415 nightly
The price is $463
Nov 8 - Nov 9
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

14. 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.
$430 nightly
The price is $479
Nov 5 - Nov 6
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage

15. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
8.8 out of 10, Excellent, (190 reviews)
"Porsche Berry Duty"
United States
Rafael G.
$323 nightly
The price is $361
Nov 26 - Nov 27
Total with taxes and fees
Canal Front home with easy Ocean access

16. 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.
$418 nightly
The price is $467
Nov 14 - Nov 15
Total with taxes and fees
Canal-Front Retreat with Dock, Pool & Open Ocean Views

17. 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.
$440 nightly
The price is $491
Nov 7 - Nov 8
Total with taxes and fees
Sailfish Haven #390 - Ocean Views, 35' seawall

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, (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.
$425 nightly
The price is $474
Nov 8 - Nov 9
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

19. 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.
$415 nightly
The price is $463
Nov 11 - Nov 12
Total with taxes and fees
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

20. Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water

Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water
Cudjoe Key
9.4 out of 10, Exceptional, (3 reviews)
"Good location to stay with family. "
United States
Phani U.
$418 nightly
The price is $466
Nov 8 - Nov 9
Total with taxes and fees
Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water
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 Summerland Key

Snorkel the vibrant coral reefs at Looe Key, where rangers can direct you to spots with fewer boats. Rent kayaks to explore the mangrove trails, then ask locals about their favorite seafood shacks serving fresh-caught Keys lobster.

A coastal pier extending into the sea, surrounded by rocky shores and greenery.

Top reviews in Summerland Key

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