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

Summerland Key Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Summerland Key holiday rentals

A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

1. 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 HK$1,111
HK$3,270 total
includes taxes & fees
13 Nov - 14 Nov
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A pool area with multiple swimming pools, lounge chairs, and palm trees.

2. 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 HK$980
HK$3,114 total
includes taxes & fees
20 Nov - 21 Nov
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is HK$1,560
HK$3,859 total
includes taxes & fees
21 Nov - 22 Nov
SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A pool area with multiple swimming pools, lounge chairs, and palm trees.

4. 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 HK$1,482
HK$3,718 total
includes taxes & fees
10 Nov - 11 Nov
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A covered outdoor area with wicker furniture and string lights.

5. 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 HK$1,222
HK$3,403 total
includes taxes & fees
11 Nov - 12 Nov
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A coastal property with a paved driveway leading to a building with a blue roof, surrounded by lush greenery and a view of the ocean.

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)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is HK$1,517
HK$3,758 total
includes taxes & fees
14 Nov - 15 Nov
Kelly's Kabin - Adorable Private Summerland Key Cottage
A waterfront balcony with a seating area, a table, and a view of the water.

7. 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 HK$1,408
HK$3,650 total
includes taxes & fees
10 Nov - 11 Nov
Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water
A pool area with multiple swimming pools, lounge chairs, and palm trees.

8. 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 HK$1,667
HK$3,934 total
includes taxes & fees
13 Nov - 14 Nov
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
A pool area with multiple swimming pools, lounge chairs, and palm trees.

9. 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 HK$1,441
HK$3,664 total
includes taxes & fees
20 Nov - 21 Nov
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
A covered outdoor seating area with a view of the ocean and palm trees.

10. 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 HK$1,445
HK$3,668 total
includes taxes & fees
14 Nov - 15 Nov
Canal-Front Retreat with Dock, Pool & Open Ocean Views
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is HK$1,168
HK$3,379 total
includes taxes & fees
11 Nov - 12 Nov
SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A pool area with multiple swimming pools, lounge chairs, and palm trees.

12. 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.
The price is HK$1,482
HK$3,718 total
includes taxes & fees
10 Nov - 11 Nov
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
A marina with boats docked, a white building with a balcony, and palm trees in the background.

13. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
8.8 out of 10, Excellent, (191 reviews)
"Porsche Berry Duty"
United States
Rafael G.
The price is HK$1,294
HK$2,826 total
includes taxes & fees
26 Nov - 27 Nov
Canal Front home with easy Ocean access
A pool area with multiple swimming pools, lounge chairs, and palm trees.

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)
"Perfect location, great price."
United States
Suzanne T.
The price is HK$1,408
HK$3,627 total
includes taxes & fees
10 Nov - 11 Nov
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A pool area with multiple swimming pools, lounge chairs, and palm trees.

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.
The price is HK$1,408
HK$3,627 total
includes taxes & fees
11 Nov - 12 Nov
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
A waterfront property with multiple buildings, a dock, and a clear view of the water.

16. 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, (5 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is HK$1,593
HK$3,718 total
includes taxes & fees
12 Nov - 13 Nov
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
A pool area with multiple swimming pools, lounge chairs, and palm trees.

17. 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 HK$1,482
HK$3,742 total
includes taxes & fees
10 Nov - 11 Nov
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A resort with multiple swimming pools, palm trees, and a view of the ocean.

18. 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, (18 reviews)
"It was great!"
United States
Jennifer B.
The price is HK$1,852
HK$4,150 total
includes taxes & fees
20 Nov - 21 Nov
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
A pool area with multiple swimming pools, lounge chairs, and palm trees.

19. Canalfront Coastal Retreat w/Open Water Views & Fishing Dock

Canalfront Coastal Retreat w/Open Water Views & Fishing Dock
Cudjoe Key
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful home with an amazing view friendly community my family and I will definitely be back highly recommend Elma’s escape "
United States
Mary T.
The price is HK$1,482
HK$3,718 total
includes taxes & fees
10 Nov - 11 Nov
Canalfront Coastal Retreat w/Open Water Views & Fishing Dock
A waterfront property with a dock, a covered outdoor seating area, and a two-story building with a balcony.

20. Florida Keys Waterfront Escape - 2BR with 44' Seawall

Florida Keys Waterfront Escape - 2BR with 44' Seawall
Cudjoe Key
The price is HK$1,482
HK$3,624 total
includes taxes & fees
10 Nov - 11 Nov
Florida Keys Waterfront Escape - 2BR with 44' Seawall
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

10/10 Excellent
"We stayed for four nights. The hotel was quiet, clean, and comfortable. The staff was very friendly. Our patio had a beautiful view of the water. We had drinks and pie in the restaurant, and they were delicious. We would definitely stay there again."
David 4-night trip
Posted less than an hour ago
Sugar Loaf Lodge

Find out more about Summerland Key

Search for holiday rentals in Summerland Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Summerland Key using one of the methods below:

  • View our selection of featured holiday rentals in Summerland Key
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  • Enter your travel dates to view the best deals on holiday rentals in Summerland Key while they last

Look no further and take a look at our great range of rental properties in Summerland Key!

Frequently asked questions

Can I find holiday rentals in Summerland Key?

Yes, there are holiday rentals close to the most popular sights in Summerland Key, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Summerland Key has to offer?

Sugarloaf Key RV Resort & Cottages: This highly rated holiday home rental in Summerland Key is located near a metro station, and offers an outdoor pool, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Summerland Key is Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball.

How many holiday rentals are there in Summerland Key?

Choose from 488 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

Florida Keys Beaches and Upper Sugarloaf Key are a couple of lovely local spots to get outside and enjoy nature. Venture Out Keys and Upper Sugarloaf Sound are other places to visit while you're in town.

What are holiday rentals like in Summerland Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Summerland Key. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.