Summerland Key Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Summerland Key vacation rentals

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, (55 reviews)
"Great area. Quiet and comfortable "
United States
nancy c.
$361 nightly
The price is $400
Jan 20 - Jan 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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, (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.
$286 nightly
The price is $317
Jan 21 - Jan 22
Total with taxes and fees
Cottage with Pool and Boat Dockage just minutes to Key West!

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
2.5 star property
Cudjoe Key
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
$540 nightly
The price is $599
Feb 3 - Feb 4
Total with taxes and fees
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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
$966 nightly
The price is $1,087
Jan 21 - Jan 22
Total with taxes and fees
Atlantic View Luxury Villa with Pool

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, (147 reviews)
"great location, we are return visitors & will be back!"
United States
Shannon W.
$397 nightly
The price is $441
Jan 20 - Jan 21
Total with taxes and fees
Quaint cottage, pool, dockage just minutes to Key West!

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
2.0 star property
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
$707 nightly
The price is $785
Jan 20 - Jan 21
Total with taxes and fees
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (176 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
$381 nightly
The price is $423
Jan 29 - Jan 30
Total with taxes and fees
Waterfront Home

Beautiful Cottage & Amenities in Gated Community

Beautiful Cottage & Amenities in Gated Community
Cudjoe Key
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, perfect for our needs"
United States
Lindsay S.
$619 nightly
The price is $687
Jan 27 - Jan 28
Total with taxes and fees
Beautiful Cottage & Amenities in Gated Community

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
$662 nightly
The price is $745
Jan 21 - Jan 22
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views

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
2.0 star property
Cudjoe Key
$611 nightly
The price is $678
Jan 20 - Jan 21
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101 reviews)
"Great location. "
United States
Davian k.
$561 nightly
The price is $623
Jan 22 - Jan 23
Total with taxes and fees
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views

135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views
2.0 star property
Cudjoe Key
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.
$655 nightly
The price is $684
Jan 28 - Jan 29
Total with taxes and fees
135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views

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

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
2.0 star property
Cudjoe Key
$604 nightly
The price is $671
Jan 20 - Jan 21
Total with taxes and fees
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

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
$548 nightly
The price is $609
Jan 20 - Jan 21
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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, (158 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
$533 nightly
The price is $592
Jan 20 - Jan 21
Total with taxes and fees
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
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.
$440 nightly
The price is $488
Feb 1 - Feb 2
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath

Southern Exposure in Cudjoe Key #49

Southern Exposure in Cudjoe Key #49
2.0 star property
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.
$659 nightly
The price is $689
Feb 8 - Feb 9
Total with taxes and fees
Southern Exposure in Cudjoe Key #49

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.
$484 nightly
The price is $538
Feb 4 - Feb 5
Total with taxes and fees
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

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.
$674 nightly
The price is $748
Jan 21 - Jan 22
Total with taxes and fees
Saltwater Serenity #392 - Ocean Views on Cudjoe Key

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

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
$655 nightly
The price is $728
Feb 14 - Feb 15
Total with taxes and fees
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Summerland Key Hotel Reviews

Find out more about Summerland Key

Everything you need to know about Summerland Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Summerland Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Summerland Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Summerland Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Summerland Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Summerland Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $317 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Summerland Key rentals

At Expedia, we put the best Summerland Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Summerland Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Summerland Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Summerland Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!: This Summerland Key vacation home rental is located on the waterfront and has a balcony, a barbecue grill, 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 vacation rentals are there in Summerland Key?

Choose from 485 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. Saddlebunch Keys and Venture Out Keys 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.