Summerland Key Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Summerland Key holiday rentals

A heated pool

Cottage in Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.2 out of 10, Very good, (55 reviews)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is HK$1,579
HK$3,120 total
includes taxes & fees
20 Jan - 21 Jan
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Villa in Summerland Key

Atlantic View Luxury Villa with Pool
3.5 star property
10.0 out of 10, Exceptional, (1 review)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is HK$4,805
HK$8,476 total
includes taxes & fees
9 Feb - 10 Feb
Atlantic View Luxury Villa with Pool
A heated pool

Cottage in Cudjoe Key

Beautiful Cottage & Amenities in Gated Community
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, perfect for our needs"
United States
Lindsay S.
The price is HK$2,088
HK$5,354 total
includes taxes & fees
27 Jan - 28 Jan
Beautiful Cottage & Amenities in Gated Community
Outdoor dining

Holiday Home in Cudjoe Key

135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Our house was beautiful and right on the water! Great sunrises and beautiful views! Fully equipped with everything you need or want! This home is the best VRBO we have rented! Would love to come back!!"
United States
Loretta F.
The price is HK$1,793
HK$5,331 total
includes taxes & fees
28 Jan - 29 Jan
135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views
Miscellaneous

Cottage in Cudjoe Key

Quaint cottage, pool, dockage just minutes to Key West!
9.0 out of 10, Wonderful, (147 reviews)
"great location, we are return visitors & will be back!"
United States
Shannon W.
The price is HK$1,949
HK$3,436 total
includes taxes & fees
20 Jan - 21 Jan
Quaint cottage, pool, dockage just minutes to Key West!
Terrace/patio

Cottage in Cudjoe Key

Waterfront Home
8.6 out of 10, Excellent, (175 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is HK$1,403
HK$3,098 total
includes taxes & fees
19 Jan - 20 Jan
Waterfront Home
A heated pool

Holiday Home in Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
The price is HK$2,661
HK$6,065 total
includes taxes & fees
18 Jan - 19 Jan
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Exterior

Cottage in Cudjoe Key

Cottage with Pool and Boat Dockage just minutes to Key West!
8.6 out of 10, Excellent, (157 reviews)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
The price is HK$1,364
HK$2,474 total
includes taxes & fees
22 Jan - 23 Jan
Cottage with Pool and Boat Dockage just minutes to Key West!
A heated pool

Holiday Home in Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
2.5 star property
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is HK$1,555
HK$4,713 total
includes taxes & fees
19 Jan - 20 Jan
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Outdoor dining

Cottage in Cudjoe Key

Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (90 reviews)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
The price is HK$2,222
HK$4,082 total
includes taxes & fees
1 Feb - 2 Feb
Canal front, dockage, 2 bedroom, 2 bath
A heated pool

Mobile Home in Cudjoe Key

Saltwater Serenity #392 - Ocean Views on Cudjoe Key
10.0 out of 10, Exceptional, (9 reviews)
"The property was really nice and super clean! Easy access and quiet neighborhood."
United States
VANESSA T.
The price is HK$2,431
HK$5,784 total
includes taxes & fees
26 Jan - 27 Jan
Saltwater Serenity #392 - Ocean Views on Cudjoe Key
Outdoor pool

Holiday Home in Summerland Key

One of the very few beach houses with a daily, rental license in the Keys.
8.8 out of 10, Excellent, (65 reviews)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is HK$3,502
HK$9,369 total
includes taxes & fees
25 Jan - 26 Jan
One of the very few beach houses with a daily, rental license in the Keys.
Terrace/patio

Holiday Home in Cudjoe Key

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful "
United States
Lisa P.
The price is HK$4,094
HK$7,958 total
includes taxes & fees
26 Jan - 27 Jan
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Outdoor dining

Holiday Home in Cudjoe Key

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
10.0 out of 10, Exceptional, (12 reviews)
"outstanding views and house is spotless!"
United States
Virginia L.
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Exterior

Holiday Home in Cudjoe Key

Southern Exposure in Cudjoe Key #49
2.0 star property
7.6 out of 10, Good, (4 reviews)
"The house is nice and sitting on the balcony feels like you're floating. It was a nice place to stay"
United States
Colleen G.
The price is HK$1,883
HK$5,308 total
includes taxes & fees
8 Feb - 9 Feb
Southern Exposure in Cudjoe Key #49
Exterior

Holiday Home in Cudjoe Key

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
9.4 out of 10, Exceptional, (101 reviews)
"Great location. "
United States
Davian k.
The price is HK$2,331
HK$4,785 total
includes taxes & fees
23 Jan - 24 Jan
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
2 bedrooms, Internet

Holiday Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
The price is HK$2,817
HK$5,920 total
includes taxes & fees
28 Jan - 29 Jan
Starlight Serenity - Hideaway w Stunning Views
A heated pool

Holiday Home in Cudjoe Key

Reel Island Retreat #273 at Venture Out in the Florida Keys
9.6 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "
United States
Lindsay C.
The price is HK$2,456
HK$5,804 total
includes taxes & fees
17 Feb - 18 Feb
Reel Island Retreat #273 at Venture Out in the Florida Keys
Exterior

Holiday Home in Cudjoe Key

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
8.6 out of 10, Excellent, (90 reviews)
"We had a great time and will be back. "
United States
Michelle K.
The price is HK$3,119
HK$6,356 total
includes taxes & fees
4 Feb - 5 Feb
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
A heated pool

Holiday Home in Cudjoe Key

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is HK$2,661
HK$6,120 total
includes taxes & fees
24 Jan - 25 Jan
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat 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

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Clean and up to date"
John 5-night trip
Posted 5 days ago
Sugarloaf Key Hotel at KOA 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?

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!: This highly rated holiday home rental in Summerland Key is located on the waterfront, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other top choices in Summerland Key are Cudjoe Cottages, swimming pool, just 20 miles from Key West and Private Secluded Ocean View & Pool Near Key West.

How many holiday rentals are there in Summerland Key?

Choose from 485 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

Florida Keys Beaches and Sugarloaf Beach are a couple of lovely local spots to get outside and enjoy nature. Saddlebunch Keys 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.