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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20
No exact matches found, but these alternatives could be just right

Recommended hotels in Summerland Key

A covered deck with chairs and umbrellas overlooking a beach.

1. Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,002 reviews)
"A very nice property, friendly and helpful staff. Very relaxing stay by the water."
United States
John
$148 nightly
The price is $167
Aug 30 - Aug 31
Total with taxes and fees
Parmer's Resort
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
7.6 out of 10, Good, (1,001 reviews)
"Fun place to stay. "
United States
Elizabeth
$99 nightly
The price is $111
Sep 27 - Sep 28
Total with taxes and fees
Looe Key Reef Resort
A waterfront building with a flat roof, large windows, and a balcony.

3. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very Good, (1,000 reviews)
"A clean comfortable room, with a lovely view from the back patio! All staff were very helpful."
United States
Marjorie
$119 nightly
The price is $134
Sep 28 - Sep 29
Total with taxes and fees
Sugar Loaf Lodge
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (110 reviews)
"Stay was great. We met the hosts and they were wonderful people."
United States
James B.
$393 nightly
The price is $436
Aug 30 - Aug 31
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A pool area with multiple swimming pools, lounge chairs, and palm trees.

5. 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.
$460 nightly
The price is $511
Sep 4 - Sep 5
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

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

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (128 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.
$456 nightly
The price is $505
Aug 31 - Sep 1
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
A balcony with white chairs and a table, overlooking a canal with houses and palm trees.

7. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
8.6 out of 10, Excellent, (188 reviews)
"Very nice property, as advertised. Great location for boating and fishing. "
United States
Lawrence L.
$343 nightly
The price is $381
Sep 9 - Sep 10
Total with taxes and fees
Canal Front home with easy Ocean access
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

8. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
$523 nightly
The price is $580
Aug 31 - Sep 1
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
$450 nightly
The price is $499
Aug 31 - Sep 1
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A beachfront property with a pool, palm trees, and a two-story building.

10. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very Good, (1 review)
$257 nightly
The price is $276
Aug 30 - Aug 31
Total with taxes and fees
Seabreeze Escape WF RV Lot 489
A large, two-story house with a balcony, a patio area with chairs, and a view of the water.

11. Venture Out RV lot 223

Venture Out RV lot 223
Cudjoe key
7.4 out of 10, Good, (3 reviews)
"We really like the location."
United States
Zunen C.
$229 nightly
The price is $242
Aug 31 - Sep 1
Total with taxes and fees
Venture Out RV lot 223
A resort with multiple swimming pools, a beach area, and a view of the ocean.

12. 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, (4 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
$560 nightly
The price is $621
Aug 30 - Aug 31
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

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, (17 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
$549 nightly
The price is $608
Aug 30 - Aug 31
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A utility box with multiple electrical outlets and warning labels, located outdoors with a residential area in the background.

14. Endless Ocean Views - RV589

Endless Ocean Views - RV589
Cudjoe Key
$257 nightly
The price is $276
Aug 30 - Aug 31
Total with taxes and fees
Endless Ocean Views - RV589
A resort with multiple swimming pools, a beach area, and a view of the ocean.

15. 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.
$560 nightly
The price is $621
Aug 30 - Aug 31
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A covered outdoor area with wicker furniture and string lights.

16. 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.
$514 nightly
The price is $571
Sep 1 - Sep 2
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.

17. 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.
$518 nightly
The price is $575
Aug 30 - Aug 31
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
A wooden deck with a hanging hammock and a view of a green landscape.

18. 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.
$514 nightly
The price is $570
Aug 30 - Aug 31
Total with taxes and fees
Starlight Serenity - Hideaway with Stunning Views

19. Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly

Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly
Cudjoe Key
$572 nightly
The price is $637
Sep 1 - Sep 2
Total with taxes and fees
Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly
A coastal residential area with houses, RVs, and a clear view of the ocean.

20. Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Cudjoe Key
$578 nightly
The price is $641
Aug 30 - Aug 31
Total with taxes and fees
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & 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 Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

8/10 Good
"The staff at Parmer’s is excellent from the check-in person to everyone that works on the grounds. However, this place had to grow on me because my initial reaction was one of disappointment. I think the pictures look much better than what’s actually there. The beach that’s advertised and looks like a sandy oasis with a clean shoreline is actually about sandy to mid calf and then algae and seaweed. A nice place to catch some rays with nice loungers but sitting on the waters edge but not for swimming or wading. The furniture is straight out of the 60’s or 70’s, but is clean and well kept. The A/C is enough to keep the cottage type bungalow cool but too far from the bathroom to keep that area cool. The pool is super clean and well maintained but water too hot during summer and would benefit from the pump keeping water flowing longer. Having said all this I found Parmer’s growing on us because of the staff, the light breakfast, eagerness of staff to please providing a fan to keep the bath cooler, the boat ramp, kayaks, shaded sitting areas by the water, fishing on property and the overall laid back feeling made me forget what wasn’t perfect and remember what hotel stays were like when I was young. No fancy Marriott’s or Sheraton, but just a place where you felt you hadn’t left home, but gained a water view with a summer breeze."
George 3-night trip
Posted 3 hours ago
Parmer's Resort

Find out more about Summerland Key

Summerland Key Chalets information

Number of reviews
3,451
Accommodation
0 Chalets
Lowest Price
$111
Highest Price
$641

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