Summerland Key Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Summerland Key vacation rentals

Property grounds

Endless Ocean Views - RV589

Endless Ocean Views - RV589
Cudjoe Key
The price is ￥31,079
￥53,134 total
includes taxes & fees
Apr 28 - Apr 29
Endless Ocean Views - RV589
Exterior

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 reviews)
"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 ￥89,652
￥163,615 total
includes taxes & fees
Apr 29 - Apr 30
Atlantic View Luxury Villa with Pool
Outdoor dining

Endless Summer Hideaway - lot 181

Endless Summer Hideaway - lot 181
Cudjoe Key
The price is ￥27,095
￥46,898 total
includes taxes & fees
Apr 30 - May 1
Endless Summer Hideaway - lot 181
A heated pool

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 ￥30,123
￥94,774 total
includes taxes & fees
Apr 30 - May 1
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A heated pool

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
9.2 out of 10, Wonderful, (9 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is ￥31,796
￥96,974 total
includes taxes & fees
Apr 28 - Apr 29
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (124 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is ￥32,274
￥82,310 total
includes taxes & fees
May 3 - May 4
Kelly's Kabin - Adorable Private Summerland Key Cottage
Property grounds

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 ￥23,907
￥48,571 total
includes taxes & fees
Apr 28 - Apr 29
Venture Out RV lot 223
Outdoor dining

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (97 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveler
The price is ￥35,861
￥72,837 total
includes taxes & fees
May 18 - May 19
Canal front, dockage, 2 bedroom, 2 bath
A heated pool

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (13 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is ￥37,654
￥103,086 total
includes taxes & fees
Apr 28 - Apr 29
Island Time #110 Ocean Views - Cudjoe Key
Outdoor pool, a heated pool

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (24 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is ￥55,783
￥109,096 total
includes taxes & fees
Apr 28 - Apr 29
Spanish Queen @Venture Out, Cudjoe Key
Exterior

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (98 reviews)
"We had a great time and will be back. "
United States
Michelle K.
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
A heated pool

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 ￥35,980
￥102,159 total
includes taxes & fees
Apr 29 - Apr 30
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Exterior

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is ￥39,686
￥89,492 total
includes taxes & fees
May 12 - May 13
SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Terrace/patio

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (14 reviews)
"We rented a boat, fished and snorkeled. Really enjoyed the patio right on the sea wall. One of the best parts of property was the stunning view of the morning sunrise!"
United States
Matt W.
The price is ￥39,845
￥118,778 total
includes taxes & fees
Apr 28 - Apr 29
House of the Rising Sun - VO479
Beach

Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (105 reviews)
"Wonderful family getaway"
United States
Anthony V.
Old Florida Style, wrap around porch, boat basin for dockage, open water
A heated pool

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is ￥40,164
￥106,866 total
includes taxes & fees
May 4 - May 5
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Exterior

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 ￥27,095
￥47,854 total
includes taxes & fees
May 4 - May 5
Seabreeze Escape WF RV Lot 489
Outdoor pool, a heated pool

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, (17 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is ￥31,127
￥71,676 total
includes taxes & fees
May 11 - May 12
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Beach

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 ￥20,919
￥81,230 total
includes taxes & fees
Apr 28 - Apr 29
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Terrace/patio

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, (7 reviews)
"Gorgeous place! Had an excellent time. Very clean and easy check-in/out process. Highly recommend!"
United States
Susan B.
The price is ￥71,123
￥145,679 total
includes taxes & fees
May 25 - May 26
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
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

6/10 Okay
"Stay was alright. A little dated and a few electrical wires on show. Needs a bit of an upgrade but it was alright for an overnight stay."
Matthew 1-night trip
Posted 11 hours 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:

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Frequently asked questions

Can I find vacation rentals in Summerland Key?

Yes, you can find vacation rentals close to top local attractions in Summerland Key, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Summerland Key?

Sugarloaf Key RV Resort & Cottages: This Summerland Key vacation home rental 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 vacation rental also comes with free parking to give you added peace of mind. Other favorite homes for rent in Summerland Key are Old Florida Style, wrap around porch, boat basin for dockage, open water and Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill.

How many vacation rentals are there in Summerland Key?

Choose from 471 Expedia vacation rentals in Summerland Key for a memorable vacation.

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 vacation rentals like in Summerland Key?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Summerland Key. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.