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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Summerland Key holiday rentals

Coffee/tea maker, fridge, microwave, oven

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

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (125 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 HK$1,518
HK$3,948 total
includes taxes & fees
4 Aug - 5 Aug
Kelly's Kabin - Adorable Private Summerland Key Cottage
Exterior detail

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
The price is HK$1,718
HK$4,916 total
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A heated pool

3. 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$1,318
HK$4,415 total
includes taxes & fees
27 Aug - 28 Aug
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Exterior

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

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (110 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
The price is HK$1,796
HK$4,180 total
includes taxes & fees
29 Aug - 30 Aug
SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Beach

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
The price is HK$1,029
HK$4,091 total
includes taxes & fees
16 Aug - 17 Aug
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Exterior

6. 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 HK$1,333
HK$2,355 total
includes taxes & fees
15 Aug - 16 Aug
Seabreeze Escape WF RV Lot 489
Outdoor dining

7. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (102 reviews)
"The bedrooms and bathrooms were a little small but everything else was fantastic. We loved the outdoor spaces."
United States
Carla R.
The price is HK$1,765
HK$3,537 total
includes taxes & fees
2 Aug - 3 Aug
Canal front, dockage, 2 bedroom, 2 bath
Exterior

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

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is HK$1,717
HK$4,115 total
includes taxes & fees
12 Aug - 13 Aug
SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor dining

9. 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 HK$1,697
HK$3,909 total
includes taxes & fees
11 Aug - 12 Aug
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Beach

10. 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
9.4 out of 10, Exceptional, (3 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is HK$1,647
HK$4,849 total
includes taxes & fees
5 Aug - 6 Aug
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A heated pool

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 HK$1,441
HK$4,610 total
includes taxes & fees
3 Aug - 4 Aug
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Beach

12. 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 HK$1,770
HK$4,886 total
includes taxes & fees
29 Aug - 30 Aug
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
A heated pool

13. 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, (10 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$1,647
HK$4,849 total
includes taxes & fees
5 Aug - 6 Aug
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Beach

14. 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
8.0 out of 10, Very good, (1 review)
"The unit was very old and tired. As such, several windows did not open, the cook top light was not working, the shower surround was cracked and the joint caulking was bad to name some examples. However, the place was spotless when we arrived and with (needed) working AC. The kitchen is WELL appointed with cooking items, some spices, and baking supplies. The washer/dryer was a treat as we travel light. The waterfront deck/patio area was great for morning coffee and evening cocktails. Venture out...
United States
Pauline Y.
The price is HK$1,359
HK$4,477 total
includes taxes & fees
15 Aug - 16 Aug
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Beach

15. Canal-view 2BR/2BA home with pool, hot tub, and dock access.

Canal-view 2BR/2BA home with pool, hot tub, and dock access.
Cudjoe Key
9.2 out of 10, Wonderful, (30 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is HK$1,647
HK$4,865 total
includes taxes & fees
31 Aug - 1 Sept
Canal-view 2BR/2BA home with pool, hot tub, and dock access.
Beach

16. 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, (16 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is HK$1,565
HK$4,764 total
includes taxes & fees
16 Aug - 17 Aug
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A heated pool

17. Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Cudjoe Key
8.0 out of 10, Very good, (1 review)
The price is HK$1,647
HK$4,872 total
includes taxes & fees
3 Aug - 4 Aug
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Beach

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
9.4 out of 10, Exceptional, (14 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
The price is HK$1,853
HK$5,135 total
includes taxes & fees
3 Aug - 4 Aug
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Beach

19. Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Cudjoe Key
8.0 out of 10, Very good, (2 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is HK$1,647
HK$4,833 total
includes taxes & fees
15 Aug - 16 Aug
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Property grounds

20. Endless Ocean Views - RV589

Endless Ocean Views - RV589
Cudjoe Key
The price is HK$1,529
HK$2,615 total
includes taxes & fees
16 Aug - 17 Aug
Endless Ocean Views - RV589
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

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

10/10 Excellent
"That was amazing!"
Krystyna 10-night trip
Posted 11 hours ago
Sugarloaf Key RV Resort & Cottages

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. Other favourite homes for rent in Summerland Key are Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West and A Tropical Luxury Getaway, Your own private resort!!.

How many holiday rentals are there in Summerland Key?

Choose from 475 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.