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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Our top choices for Summerland Key holiday rentals

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (111 reviews)
"$125.00 extra charge when arriving. Almost all the remotes needed batteries. Furniture was all shoved up against walls, everything needed to be set back up. Kayaks were under house buried under a massive amount of junk and covered with sand and debris. A/C worked on and off. A/c window unit drain poured water on steps down to sea wall making them very slippery all the time. May have been a very nice place years ago but really shows its age and poor maintenance. Did not feel like calling the...
United States
Ken
The price is AU$567
includes taxes & fees
1 Sept - 2 Sept
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

2. 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.
The price is AU$699
includes taxes & fees
1 Sept - 2 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage

3. 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 AU$710
includes taxes & fees
4 Sept - 5 Sept
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

4. 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.
The price is AU$516
includes taxes & fees
10 Sept - 11 Sept
Canal Front home with easy Ocean access

5. 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 AU$802
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is AU$603
includes taxes & fees
1 Sept - 2 Sept
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

7. 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.
The price is AU$333
includes taxes & fees
1 Sept - 2 Sept
Venture Out RV lot 223

8. 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 AU$382
includes taxes & fees
1 Sept - 2 Sept
Seabreeze Escape WF RV Lot 489

9. Endless Ocean Views - RV589

Endless Ocean Views - RV589
Cudjoe Key
The price is AU$382
includes taxes & fees
1 Sept - 2 Sept
Endless Ocean Views - RV589

10. 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 AU$795
includes taxes & fees
1 Sept - 2 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

11. 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.
The price is AU$860
includes taxes & fees
1 Sept - 2 Sept
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

12. 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 AU$860
includes taxes & fees
1 Sept - 2 Sept
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

13. 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, (32 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.
The price is AU$639
includes taxes & fees
16 Sept - 17 Sept
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

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, (17 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AU$840
includes taxes & fees
1 Sept - 2 Sept
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

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

Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly
Cudjoe Key
The price is AU$895
includes taxes & fees
2 Sept - 3 Sept
Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly

16. 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 AU$813
includes taxes & fees
1 Sept - 2 Sept
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

17. 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
The price is AU$885
includes taxes & fees
1 Sept - 2 Sept
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

18. Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
9.0 out of 10, Wonderful, (11 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 AU$857
includes taxes & fees
8 Sept - 9 Sept
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

19. 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 AU$824
includes taxes & fees
15 Sept - 16 Sept
Starlight Serenity - Hideaway w Stunning Views

20. 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)
"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 AU$851
includes taxes & fees
9 Sept - 10 Sept
Canalfront Coastal Retreat w/Open Water Views & Fishing Dock
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

Find out more about Summerland Key

Everything you need to know about Summerland Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Summerland Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Summerland Key holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Summerland Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Summerland Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Summerland Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Summerland Key holiday rentals we have selected for you start as low as AU$699 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Summerland Key rentals

At Expedia, we put the best Summerland Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Summerland Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Summerland Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Summerland Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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. Other favourite homes for rent in Summerland Key are Cudjoe Cottages, swimming pool, just 20 miles from Key West and One of the very few beach houses with a daily, rental license in the Keys..

How many holiday rentals are there in Summerland Key?

Choose from 480 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. Pye Key and Venture Out Keys 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.