Summerland Key Holiday Rentals

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Our top choices for Summerland Key holiday rentals

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)
"great location, we are return visitors & will be back!"
United States
Shannon W.
The price is NZ$763
includes taxes & fees
2 Jan - 3 Jan
Quaint cottage, pool, dockage just minutes to Key West!

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, (54)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is NZ$733
includes taxes & fees
10 Jan - 11 Jan
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is NZ$1,079
includes taxes & fees
18 Jan - 19 Jan
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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, (154)
"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 NZ$536
includes taxes & fees
9 Jan - 10 Jan
Cottage with Pool and Boat 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, (164)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
United States
Andrea S.
The price is NZ$654
includes taxes & fees
19 Jan - 20 Jan
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

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, (4)
"Beautiful "
United States
Lisa P.
The price is NZ$1,762
includes taxes & fees
3 Jan - 4 Jan
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

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, (148)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is NZ$1,250
includes taxes & fees
2 Jan - 3 Jan
Cudjoe Cottages, swimming pool, just 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, (89)
"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.
The price is NZ$775
includes taxes & fees
5 Jan - 6 Jan
Canal front, dockage, 2 bedroom, 2 bath

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Cudjoe Key
10.0 out of 10, Exceptional, (12)
"outstanding views and house is spotless!"
United States
Virginia L.
The price is NZ$1,576
includes taxes & fees
14 Jan - 15 Jan
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

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, (89)
"Nice house in a great location. "
United States
Jarrod L.
The price is NZ$1,435
includes taxes & fees
6 Jan - 7 Jan
Old Florida Style, wrap around porch, boat basin for dockage, open water

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (49)
"The Post Card Point was absolutely stunning. Very clean and welcoming. Perfect access to fishing, diving, lobstering! Filet Table right on the water. We loved it :) will definitely be back!!!"
United States
Dave J.
The price is NZ$1,642
includes taxes & fees
2 Jan - 3 Jan
Post Card Point #319 - Ocean Views!

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)
"The property was really nice and super clean! Easy access and quiet neighborhood."
United States
VANESSA T.
The price is NZ$1,286
includes taxes & fees
3 Jan - 4 Jan
Saltwater Serenity #392 - Ocean Views on Cudjoe Key

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (143)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
The price is NZ$1,745
includes taxes & fees
6 Jan - 7 Jan
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

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)
"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 NZ$1,773
includes taxes & fees
16 Jan - 17 Jan
Atlantic View Luxury Villa with Pool

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

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very good, (119)
"Great experience "
United States
Peyton S.
The price is NZ$1,143
includes taxes & fees
2 Jan - 3 Jan
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Spanish Queen @Venture Out, 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 NZ$1,229
includes taxes & fees
4 Jan - 5 Jan
Spanish Queen @Venture Out, Cudjoe Key

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is NZ$2,054
includes taxes & fees
7 Jan - 8 Jan
One of the very few beach houses with a daily, rental license in the Keys.

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

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is NZ$1,053
includes taxes & fees
10 Jan - 11 Jan
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Reel Island Retreat #273 at Venture Out in the Florida Keys

Reel Island Retreat #273 at Venture Out in the Florida Keys
Cudjoe Key
9.6 out of 10, Exceptional, (7)
"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "
United States
Lindsay C.
The price is NZ$1,219
includes taxes & fees
11 Jan - 12 Jan
Reel Island Retreat #273 at Venture Out in the Florida Keys

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (175)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is NZ$820
includes taxes & fees
10 Jan - 11 Jan
Waterfront Home
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

Everything you need to know about Summerland Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Summerland Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Summerland Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Summerland Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Summerland Key holiday rentals we have selected for you start as low as NZ$536 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Summerland Key rentals

At Expedia, we put the best Summerland Key holiday 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 holiday.

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 holiday rentals in Summerland Key?

Yes, there are holiday rentals close to the most popular sights in Summerland Key, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Summerland Key has to offer?

Private Secluded Ocean View & Pool Near Key West: This highly rated holiday home rental in Summerland Key is located near the beach, and has an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. It offers a private garden, 1 hot tub and table football so that you can immerse yourself in your holiday. Some other top choices in Summerland Key are COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking! and Cudjoe Cottages, swimming pool, just 20 miles from Key West.

How many holiday rentals are there in Summerland Key?

Choose from 484 Expedia holiday rentals in Summerland Key for a memorable holiday.

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 holiday rentals like in Summerland Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Summerland Key. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.