Summerland Key Vacation Rentals

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Our top choices for Summerland Key vacation rentals

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
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 CA $892
CA $1,542 total
includes taxes & fees
Feb 9 - Feb 10
Atlantic View Luxury Villa with Pool

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (103 reviews)
"Great location. "
United States
Davian k.
The price is CA $231
CA $628 total
includes taxes & fees
Feb 8 - Feb 9
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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, (55 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
The price is CA $338
CA $629 total
includes taxes & fees
Feb 23 - Feb 24
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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, (165 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is CA $246
CA $443 total
includes taxes & fees
Feb 15 - Feb 16
Cottage with swimming pool and dockage, just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
The price is CA $277
CA $480 total
includes taxes & fees
Feb 8 - Feb 9
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is CA $273
CA $832 total
includes taxes & fees
Feb 11 - Feb 12
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (177 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is CA $342
CA $668 total
includes taxes & fees
Feb 23 - Feb 24
Waterfront Home

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
The price is CA $342
CA $920 total
includes taxes & fees
Mar 3 - Mar 4
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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 CA $232
CA $412 total
includes taxes & fees
Mar 3 - Mar 4
Seabreeze Escape WF RV Lot 489

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
The price is CA $287
CA $841 total
includes taxes & fees
Feb 27 - Feb 28
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Relax by Florida Keys Beaches, just a 7-min drive away

Relax by Florida Keys Beaches, just a 7-min drive away
Cudjoe Key
9.8 out of 10, Exceptional, (201 reviews)
"Will definitely stay here again "
United States
Jeannine R.
The price is CA $376
CA $899 total
includes taxes & fees
Feb 27 - Feb 28
Relax by Florida Keys Beaches, just a 7-min drive away

Endless Summer Hideaway - lot 181

Endless Summer Hideaway - lot 181
Cudjoe Key
The price is CA $233
CA $413 total
includes taxes & fees
Mar 4 - Mar 5
Endless Summer Hideaway - lot 181

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
The price is CA $467
CA $1,077 total
includes taxes & fees
Feb 25 - Feb 26
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

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
7.6 out of 10, Good, (13 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is CA $338
CA $706 total
includes taxes & fees
Feb 11 - Feb 12
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is CA $1,091
CA $2,115 total
includes taxes & fees
Feb 17 - Feb 18
The Hemingway - Beach Houses Key West

Saltwater Serenity #392 - Ocean Views on Cudjoe Key

Saltwater Serenity #392 - Ocean Views on Cudjoe Key
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 CA $428
CA $1,030 total
includes taxes & fees
Feb 10 - Feb 11
Saltwater Serenity #392 - Ocean Views on Cudjoe Key

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (123 reviews)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
The price is CA $376
CA $833 total
includes taxes & fees
Mar 7 - Mar 8
Kelly's Kabin - Adorable Private Summerland Key Cottage

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

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Cudjoe Key
The price is CA $359
CA $941 total
includes taxes & fees
Feb 11 - Feb 12
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Southern Exposure in Cudjoe Key #49

Southern Exposure in Cudjoe Key #49
Cudjoe Key
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 CA $313
CA $944 total
includes taxes & fees
Feb 8 - Feb 9
Southern Exposure in Cudjoe Key #49

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
8.0 out of 10, Very good, (2 reviews)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
United States
Samat S.
The price is CA $2,204
CA $3,738 total
includes taxes & fees
Feb 23 - Feb 24
Private and Exclusive Beach Getaway
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Summerland Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West and Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West.

How many vacation rentals are there in Summerland Key?

Choose from 475 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.