Summerland Key Vacation Rentals

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Nov 14 - Nov 15
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Vacation Rentals in Summerland Key

Pool
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Cudjoe Key
10.0 out of 10, Exceptional, (4)
"Excellent stay Quiet clean and comfortable Thank you for making our vacation a fantastic experience "
United States
Debbie W.
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Fridge, microwave, oven, stovetop
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Cudjoe Key
8.8 out of 10, Excellent, (153)
"The property was excellent. The location was perfect. Quiet and relaxing. "
United States
Jonathan K.
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Outdoor dining
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Cudjoe Key
9.6 out of 10, Exceptional, (45)
"Loved it! The view is unbelievable! Such a such place and tastefully decorated. Beds were comfy and it had just what we needed to cook. Nice big table to play games. We will definitely book again! "
United States
Jennifer B.
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key
8.8 out of 10, Excellent, (147)
"Nice location. Comfortable place although the couch and living room chair were old and stained. "
United States
Charles V.
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
8.2 out of 10, Very Good, (48)
"Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children"
United States
Nathalie F.
The price is ￥20,886
￥49,082 total
includes taxes & fees
Nov 30 - Dec 1
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key
8.6 out of 10, Excellent, (150)
"An amazing place to come home to after a long day in the keys. Having a car is a must, but I would recommend time after time again and hope to come back again in the future"
United States
Travis W.
Cottage with Pool and Boat Dockage just minutes to Key West!
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
8.8 out of 10, Excellent, (73)
"Place was everything we needed, would definitely stay again "
United States
James h.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor dining
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

Cudjoe Key
9.8 out of 10, Exceptional, (213)
"Awesome location, lots of amenities, lots of rules too so be aware! House was super clean and well stocked, Last Key Realty was very helpful and responsive!"
United States
Marti B.
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Cudjoe
9.8 out of 10, Exceptional, (229)
"My mom and I were absolutely amazed by the property, we loved everything and hope to come back again!"
United States
Emma T.
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Miscellaneous
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!

Cudjoe Key
9.0 out of 10, Wonderful, (158)
"Wonderful stay with great property and pool. Very well maintained!"
United States
Eric E.
Cottage with swimming pool and dockage, just minutes to Key West!
Beach
Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,

Little Torch Key
8.6 out of 10, Excellent, (192)
"Wonderful, cozy cottage facing sunrise on the water. We had very efficient communication with the property manager for any details. Dog friendly, designated parking, great full kitchen and room for at least 3 adults. I would definitely recommend this location, we will be back!"
United States
Suzanne R.
Direct Oceanfront Cottage-Sunrise View- #2,
Property grounds
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, (85)
"Just a beautiful location, paradise. Spent mornings in the covered porch, husband loved the lagoon for fishing. We brought kayaks and the kids loved it. The dogs enjoyed the large property as well. "
United States
Kendra K.
The price is ￥46,413
￥107,949 total
includes taxes & fees
Nov 19 - Nov 20
Old Florida Style, wrap around porch, boat basin for dockage, open water
Miscellaneous
Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!

Cudjoe Key
9.0 out of 10, Wonderful, (143)
"My family loved the cottage. The pool and fishing dock were awesome."
United States
Leslie B.
Quaint cottage, pool, dockage just minutes to Key West!
Beach nearby
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
8.8 out of 10, Excellent, (88)
"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "
United States
Mitchell D O.
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Fridge, microwave, oven, stovetop
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
8.8 out of 10, Excellent, (89)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
United States
James P.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Cudjoe Key
10.0 out of 10, Exceptional, (31)
"Very clean, it hit all the things we wanted i.e. upstairs outdoor porch. "
United States
Kevin S.
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
A heated pool
Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft

Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft

Cudjoe Key
9.4 out of 10, Exceptional, (164)
"The space and location were perfect for my husband and I. We brought our pontoon and it was nice to launch 3 blocks from the property and to park at the dock, at the house. We enjoyed the pool and the beautiful area. The owner kept in contact with us and was wonderful to communicate with. We would stay at this property again. "
United States
Tina
Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft
Terrace/patio
Waterfront Home

Waterfront Home

Cudjoe Key
8.6 out of 10, Excellent, (173)
"Venture out is more of a retirement community than a family resort. The location is ideal and the house was well appointed "
United States
CAROLINE L.
Waterfront Home
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key
9.0 out of 10, Wonderful, (88)
"Community is great, location in the Keys is great, house was perfect for our family of 3."
United States
Christina H.
The price is ￥27,074
￥60,607 total
includes taxes & fees
Nov 16 - Nov 17
Canal front, dockage, 2 bedroom, 2 bath
Property grounds
Keys House - Venture Out Lot 220

Keys House - Venture Out Lot 220

2.5 star property
Summerland Key
9.8 out of 10, Exceptional, (6)
"Nice location! Great balcony!"
United States
Maso O.
Keys House - Venture Out Lot 220
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

10/10 Excellent
"Excellent service and ammenities. We enjoyed our stay, very personable resort and we took pleasure in getting to know the other patrons at the pool. The Resort is in the perfect central location, we travelled to both Islamorada and Key West a couple of days. A fishing charter picked us up right at the Resort dock. We took our catch down to Kiki's and they cooked it up for us. Also, nightly live entertainment at Kiki's just down the road. "
Tara 6-night trip
Posted 5 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:

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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?

Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes: This Summerland Key vacation home rental is located on the beach and has an outdoor pool, a balcony, and a barbecue grill 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 JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community! and COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!.

How many vacation rentals are there in Summerland Key?

Choose from 498 Expedia vacation rentals in Summerland Key for a memorable vacation.

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. Venture Out Keys and Upper Sugarloaf Key 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.