A coastal road with a beach on one side and a marina with boats on the other.

Summerland Key Chalets

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7
No exact matches found, but these alternatives could be just right

Recommended hotels in Summerland Key

A waterfront building with a flat roof, large windows, and a balcony.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very good, (1,003 reviews)
"Hostess was wonderful. The rooms traditional with the most amazing views of the gulf. coffee and hot tea appreciated. both the tiki and the restaurant were closed but will like to try on next trip south. Definitely nice place to stay on way down to key west."
United States
morgan
$119 nightly
The price is $134
Oct 15 - Oct 16
Total with taxes and fees
Sugar Loaf Lodge
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

2. Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
Summerland Key
7.8 out of 10, Good, (1,004 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
$111 nightly
The price is $125
Oct 15 - Oct 16
Total with taxes and fees
Looe Key Reef Resort
A covered deck with chairs and umbrellas overlooking a beach.

3. Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,003 reviews)
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
United States
Mireya
$198 nightly
The price is $223
Nov 1 - Nov 2
Total with taxes and fees
Parmer's Resort
A pool area with multiple swimming pools, lounge chairs, and palm trees.

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.
$372 nightly
The price is $413
Oct 15 - Oct 16
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Exterior

5. Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor

Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor
Cudjoe Key
$109 nightly
The price is $120
Oct 15 - Oct 16
Total with taxes and fees
Cozy 1-bedroom apartment with WiFi, AC in charming Cudjoe Key large outdoor
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (98 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
$388 nightly
The price is $431
Oct 18 - Oct 19
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A coastal residential area with houses, RVs, and a clear view of the ocean.

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
$486 nightly
The price is $540
Oct 15 - Oct 16
Total with taxes and fees
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
A swimming pool with lounge chairs and palm trees, surrounded by a fence and a building in the background.

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.
$410 nightly
The price is $455
Oct 15 - Oct 16
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A small, single-story building with a blue exterior, a white door, and a red 'R' sign indicating a restaurant.

9. 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.
$455 nightly
The price is $505
Oct 15 - Oct 16
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
$386 nightly
The price is $430
Oct 15 - Oct 16
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A beachfront property with a pool, palm trees, and a two-story building.

11. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very good, (1 review)
$243 nightly
The price is $261
Oct 15 - Oct 16
Total with taxes and fees
Seabreeze Escape WF RV Lot 489
A covered outdoor area with wicker furniture and string lights.

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
8.0 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.
$427 nightly
The price is $475
Oct 15 - Oct 16
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A resort with multiple swimming pools, a beach area, and a marina.

13. 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.
$439 nightly
The price is $487
Oct 15 - Oct 16
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Outdoor dining

14. 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.
$457 nightly
The price is $507
Oct 15 - Oct 16
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A resort with multiple swimming pools, a beach area, and a marina.

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
9.6 out of 10, Exceptional, (7 reviews)
"Clean and excellent water access"
United States
Chris P.
$457 nightly
The price is $507
Oct 15 - Oct 16
Total with taxes and fees
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
A resort with multiple swimming pools, a beach area, and a view of the ocean.

16. 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.
$468 nightly
The price is $520
Oct 15 - Oct 16
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A waterfront balcony with a seating area, a table, and a view of the water.

17. 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.
$463 nightly
The price is $513
Oct 15 - Oct 16
Total with taxes and fees
Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water
A swimming pool with palm trees and a view of the sea.

18. Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key West

Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key West
Cudjoe Key
$133 nightly
The price is $147
Oct 15 - Oct 16
Total with taxes and fees
Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key West
A resort with multiple swimming pools, a beach area, and a view of the ocean.

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

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Cudjoe Key
8.0 out of 10, Very good, (2 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
$468 nightly
The price is $520
Oct 18 - Oct 19
Total with taxes and fees
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
A pool area with multiple swimming pools, lounge chairs, and palm trees.

20. 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.
$457 nightly
The price is $507
Oct 15 - Oct 16
Total with taxes and fees
Canal-Front Retreat with Dock, Pool & Open Ocean 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 Summerland Key Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

8/10 Good
"Balcony"
Martin 1-night trip
Posted 11 hours ago
Sugar Loaf Lodge

Find out more about Summerland Key

Summerland Key Chalets information

Number of reviews
3,287
Accommodation
0 Chalets
Lowest Price
$125
Highest Price
$540

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