Summerland Key Vacation Rentals

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Vacation Rentals in Summerland Key

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 ¥21,084
¥49,548 total
includes taxes & fees
Dec 1 - Dec 2
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
9.2 out of 10, Wonderful, (161)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
The price is ¥23,427
¥49,392 total
includes taxes & fees
Dec 6 - Dec 7
Cottage with Pool and 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, (151)
"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 ¥19,523
¥39,514 total
includes taxes & fees
Dec 15 - Dec 16
Cottage with Pool and Boat Dockage just minutes to Key West!

DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is ¥26,394
¥71,608 total
includes taxes & fees
Dec 1 - Dec 2
DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Starlight Serenity - Hideaway w Stunning Views

2.0 star property
Summerland Key
The price is ¥34,558
¥91,061 total
includes taxes & fees
Dec 2 - Dec 3
Starlight Serenity - Hideaway w Stunning Views

The Hemingway - Beach Houses Key West

Upper Sugarloaf Key
9.8 out of 10, Exceptional, (7)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is ¥222,478
¥370,070 total
includes taxes & fees
Dec 24 - Dec 25
The Hemingway - Beach Houses Key West

Endless Summer Hideaway - lot 181

Cudjoe Key
The price is ¥15,618
¥32,876 total
includes taxes & fees
Dec 2 - Dec 3
Endless Summer Hideaway - lot 181

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
9.8 out of 10, Exceptional, (121)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
The price is ¥35,141
¥84,767 total
includes taxes & fees
Dec 14 - Dec 15
Kelly's Kabin - Adorable Private Summerland Key Cottage

DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is ¥38,889
¥87,383 total
includes taxes & fees
Dec 3 - Dec 4
DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Cudjoe Key
9.8 out of 10, Exceptional, (26)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
United States
Patrick M.
The price is ¥46,698
¥98,120 total
includes taxes & fees
Dec 13 - Dec 14
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Galleon Getaway #533- Oceanfront Community

Cudjoe Key
The price is ¥22,958
¥84,554 total
includes taxes & fees
Dec 4 - Dec 5
Galleon Getaway #533- Oceanfront Community

Seabreeze Escape WF RV Lot 489

Cudjoe Key
8.0 out of 10, Very Good, (1)
The price is ¥21,865
¥40,841 total
includes taxes & fees
Dec 1 - Dec 2
Seabreeze Escape WF RV Lot 489

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cutthroat Harbor Estates
8.4 out of 10, Very Good, (118)
"Great experience "
United States
Peyton S.
The price is ¥35,141
¥84,202 total
includes taxes & fees
Dec 1 - Dec 2
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Saltwater Serenity #392 - Ocean Views on Cudjoe Key

Cudjoe Key
10.0 out of 10, Exceptional, (7)
"Excellent place to stay on the water store right on premises will definitely be back have stayed 2 times this year "
United States
Anonymous traveler
The price is ¥36,898
¥101,641 total
includes taxes & fees
Dec 1 - Dec 2
Saltwater Serenity #392 - Ocean Views on Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
Cudjoe Key
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is ¥36,898
¥101,641 total
includes taxes & fees
Dec 1 - Dec 2
Island Time #110 Ocean Views - Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

Cudjoe Key
9.4 out of 10, Exceptional, (19)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is ¥54,663
¥106,280 total
includes taxes & fees
Dec 1 - Dec 2
Spanish Queen @Venture Out, Cudjoe Key

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Cudjoe Key
The price is ¥29,518
¥92,402 total
includes taxes & fees
Dec 1 - Dec 2
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

The Lighthouse - Beach Houses Key West

Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The Lighthouse - Beach Houses Key West

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

Cudjoe Key
10.0 out of 10, Exceptional, (2)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Venture Out RV lot 223

Cudjoe key
7.4 out of 10, Good, (3)
"We really like the location."
United States
Zunen C.
Venture Out RV lot 223
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

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?

Private Secluded Ocean View & Pool Near Key West: This Summerland Key vacation home rental is located near the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a hot tub, and foosball so you can immerse yourself in your vacation. Some other top choices in Summerland Key are Old Florida Style, wrap around porch, boat basin for dockage, open water and OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS.

How many vacation rentals are there in Summerland Key?

Choose from 494 Expedia vacation rentals in Summerland Key for a memorable vacation.

What can I see and do in Summerland Key?

Upper Sugarloaf Key and Florida Keys Beaches are a couple of lovely local spots to get outside and enjoy nature. Venture Out Keys and Coupon Bight Aquatic Preserve 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.