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

Search Castles in Summerland Key from CA $162

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Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6
No exact matches found, but these alternatives could be just right

Recommended hotels in Summerland Key

A hotel with a registration parking office, surrounded by palm trees and illuminated by green and yellow lights.

1. Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,001 reviews)
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
United States
Mireya
The price is CA $180
CA $250 total
includes taxes & fees
Nov 2 - Nov 3
Parmer's Resort
A waterfront building with a flat roof, large windows, and a balcony.

2. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very good, (1,000 reviews)
"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"
United States
Richard
The price is CA $170
CA $191 total
includes taxes & fees
Oct 8 - Oct 9
Sugar Loaf Lodge
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

3. Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
Summerland Key
7.8 out of 10, Good, (1,003 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
The price is CA $144
CA $162 total
includes taxes & fees
Oct 14 - Oct 15
Looe Key Reef Resort
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (98 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is CA $198
CA $604 total
includes taxes & fees
Oct 9 - Oct 10
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A marina with a boat house, a white RV, and several buildings with blue roofs.

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.
The price is CA $178
CA $596 total
includes taxes & fees
Oct 8 - Oct 9
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A small, single-story building with a blue exterior and a slanted roof.

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, (129 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.
The price is CA $282
CA $729 total
includes taxes & fees
Oct 11 - Oct 12
Kelly's Kabin - Adorable Private Summerland Key Cottage
A single-story mobile home with a beige exterior and a blue roof, surrounded by lush tropical vegetation.

7. 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 CA $224
CA $655 total
includes taxes & fees
Oct 9 - Oct 10
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated 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
The price is CA $262
CA $826 total
includes taxes & fees
Oct 7 - Oct 8
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is CA $227
CA $640 total
includes taxes & fees
Oct 14 - Oct 15
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A coastal residential area with houses, RVs, and a clear view of the ocean.

10. 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 CA $322
CA $779 total
includes taxes & fees
Oct 8 - Oct 9
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
A small, single-story mobile home with a covered porch, surrounded by palm trees and other tropical vegetation.

11. 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.
The price is CA $247
CA $683 total
includes taxes & fees
Oct 14 - Oct 15
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Exterior

12. 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 CA $284
CA $731 total
includes taxes & fees
Oct 14 - Oct 15
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A beachfront property with a pool, palm trees, and a two-story building.

13. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very good, (1 review)
The price is CA $214
CA $393 total
includes taxes & fees
Oct 8 - Oct 9
Seabreeze Escape WF RV Lot 489
Exterior

14. 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 CA $299
CA $749 total
includes taxes & fees
Oct 14 - Oct 15
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A marina with RVs and mobile homes, a swimming pool, and a view of the ocean.

15. 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 CA $262
CA $703 total
includes taxes & fees
Oct 8 - Oct 9
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
A mobile home with a sliding door, a bicycle parked outside, and a bench.

16. 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 CA $284
CA $731 total
includes taxes & fees
Oct 8 - Oct 9
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
A waterfront property with a covered patio, outdoor seating, and a pool.

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.
The price is CA $284
CA $731 total
includes taxes & fees
Oct 8 - Oct 9
Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water
A two-story house with a balcony and a staircase leading to the upper level.

18. 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 CA $398
CA $968 total
includes taxes & fees
Oct 13 - Oct 14
Starlight Serenity - Hideaway w Stunning Views
Water Views

19. 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 CA $306
CA $885 total
includes taxes & fees
Oct 14 - Oct 15
Starlight Serenity - Hideaway with Stunning Views
A two-story building with a balcony, a covered entrance, and a parking area with a bicycle.

20. Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Really nice unit, well equipped, and quiet.Would stay again for sure."
United States
Tom A.
The price is CA $499
CA $975 total
includes taxes & fees
Oct 12 - Oct 13
Spanish Queen @Venture Out, Cudjoe Key
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

Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"This is a great inexpensive place to stay. Room was clean. Resort is showing some wear but is still good. Staff are very helpful with local recommendations. There is a great gas station next door with some items for sale in case you forget something. I would stay again."
Brandy 2-night trip
Posted 13 hours ago
Looe Key Reef Resort

Find out more about Summerland Key

Summerland Key Castles information

Number of reviews
2,300
Accommodation
0 Castles
Lowest Price
CA $162
Highest Price
CA $975

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