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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Summerland Key holiday rentals

A covered outdoor seating area with white chairs and tables, overlooking turquoise waters and distant islands.

1. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (148 reviews)
"Everything was exactly as described and we could not be happier. The community that this house is in is very pleasant as well"
United States
Jaret R.
The price is HK$2,780
HK$5,502 total
includes taxes & fees
31 Oct - 1 Nov
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is HK$1,561
HK$3,713 total
includes taxes & fees
21 Nov - 22 Nov
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A pool area with multiple swimming pools, lounge chairs, and palm trees.

3. 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$1,409
HK$3,778 total
includes taxes & fees
31 Oct - 1 Nov
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
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.
The price is HK$882
HK$3,123 total
includes taxes & fees
1 Nov - 2 Nov
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A pool area with multiple swimming pools, lounge chairs, and palm trees.

5. 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$1,668
HK$4,109 total
includes taxes & fees
31 Oct - 1 Nov
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, under a cloudy sky.

6. Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
8.0 out of 10, Very good, (21 reviews)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is HK$1,942
HK$4,004 total
includes taxes & fees
1 Nov - 2 Nov
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A pool area with multiple swimming pools, lounge chairs, and palm trees.

7. 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$1,483
HK$3,917 total
includes taxes & fees
31 Oct - 1 Nov
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A pool area with multiple swimming pools, lounge chairs, and palm trees.

8. 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$1,483
HK$3,877 total
includes taxes & fees
1 Nov - 2 Nov
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A waterfront property with multiple buildings, a dock, and a clear view of the water.

9. 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$1,668
HK$4,109 total
includes taxes & fees
31 Oct - 1 Nov
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
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.

10. 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$1,518
HK$3,823 total
includes taxes & fees
3 Nov - 4 Nov
Kelly's Kabin - Adorable Private Summerland Key Cottage
A pool area with multiple swimming pools, lounge chairs, and palm trees.

11. 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, (6 reviews)
"The property was perfect for a family. Boat launch and marina on site. Kids loved the pool. The amenities were perfect. Such a relaxing stay in the lower keys. To have off street parking and a place to keep your boat and trailer is huge. Wonderful place"
United States
Duvall's M.
The price is HK$1,483
HK$3,877 total
includes taxes & fees
31 Oct - 1 Nov
Canalfront Coastal Retreat w/Open Water Views & Fishing Dock
Property grounds

12. 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.
The price is HK$1,594
HK$4,042 total
includes taxes & fees
8 Nov - 9 Nov
Sailfish Haven #390 - Ocean Views, 35' seawall
A balcony with wicker furniture, a wooden table, and a view of the surrounding area.

13. 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 HK$2,746
HK$5,403 total
includes taxes & fees
4 Nov - 5 Nov
Spanish Queen @Venture Out, Cudjoe Key
A waterfront property with multiple buildings, including a house with a balcony and a covered area, connected by a dock.

14. Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape

Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape
Cudjoe Key
8.8 out of 10, Excellent, (3 reviews)
"Great location and accommodations "
United States
Brandie Lane c.
The price is HK$1,853
HK$4,342 total
includes taxes & fees
31 Oct - 1 Nov
Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape
A covered outdoor area with a grill, wicker furniture, and a table with drinks, overlooking the sea.

15. Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
Cudjoe Key
9.8 out of 10, Exceptional, (25 reviews)
"We had a nice stay."
United States
Kandie B.
The price is HK$3,542
HK$6,942 total
includes taxes & fees
14 Nov - 15 Nov
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
A pier with a palm tree, clear turquoise water, and a distant shoreline.

16. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (33 reviews)
"This place was great! As advertised. It is located within a resort community, so it is safe with lots of amenities. "
United States
BRIAN S.
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

17. 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$1,112
HK$3,413 total
includes taxes & fees
2 Nov - 3 Nov
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A view from a balcony overlooking a beach with a clear sky and calm sea.

18. Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful views from the deck. The resort was quiet and peaceful. "
United States
G G.
The price is HK$3,521
HK$6,430 total
includes taxes & fees
3 Nov - 4 Nov
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is HK$1,169
HK$3,381 total
includes taxes & fees
9 Nov - 10 Nov
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A wooden deck with a hanging hammock and a view of a green landscape.

20. 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 HK$2,724
HK$5,783 total
includes taxes & fees
30 Nov - 1 Dec
Starlight Serenity - Hideaway w Stunning 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

Parmer's Resort

Parmer's Resort

8/10 Good
"The privacy was fantastic, the staff was helpful and we were right down the street from Robbie’s"
Mark 1-night trip
Posted 2 days ago
Parmer's Resort

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.