Summerland Key Vacation Rentals

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Vacation Rentals in Summerland Key

Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, 47 reviews
"So glad we found this location. Nice and peaceful but close to anything we needed. Sitting on the porch was so relaxing, watching boats go by. The house was very comfortable. Only wish the 2nd bedroom had a working TV. Our host was quick to answer any issue we had and left some great suggestions on places to eat. I would definitely return to enjoy this beautiful location"
Old Florida Style, wrap around porch, boat basin for dockage, open water
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, 186 reviews
"All amenities were operational and organized. check in/check out process was easy. i thoroughly enjoyed my stay with friends. thanks"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, 204 reviews
"Beautiful and quiet location. Close to Key West yet just far enough to be away from the crowds. Family thoroughly enjoyed it. Everything is as pictured and immaculately clean, truly a gem. Melanie was friendly, always available and always responsive."
The price is CA $477
CA $605 total
includes taxes & fees
Jun 18 - Jun 19
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, 53 reviews
"It was a nice Key West cottage with beautiful views of Cudjoe Bay."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Property grounds
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, 13 reviews
"Annual family trip to the keys, a little fishing, a little snorkeling, some sailing……this place is soo convenient for all. Right on the water, close to everything. Second time we’ve stayed in this house. Will definitely return. Kudos to Dan and Wendy, made everything so easy. Thank you!!"
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, 90 reviews
"Explain to people that there is an opportunity to park the truck with a trailer and that there are ramps for the boat because I myself did not take my boat thinking that there was nothing like that. Thanks "
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Waterfront Home
Exterior
Waterfront Home
8.8 out of 10, Excellent, 141 reviews
"Would definitely come back!!!!"
Waterfront Home
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
Sun loungers, beach towels
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
10.0 out of 10, Exceptional, 26 reviews
"Very comfortable low key rental. The house was clean and setup perfectly for what we needed. The pool was very warm more like an oversized hot tub but it was still nice to hang out in after a day out. Loved the outdoor shower! Will definitely keep this on our list of places to stay for our next trip down!"
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Sun loungers, beach towels
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
9.6 out of 10, Exceptional, 39 reviews
"Ww stayed for 6 nights as our first time in the Keys. The property is very well manicured with everything you'll need. We had a small issue with one cottage that was quickly rectified by the owners. Hope Nd Glenn were terrific! Not sure if we'll ever return to the Keys, but we highly recommend The Hidden Hammick to anyone visiting the area."
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.2 out of 10, Very good, 27 reviews
"This place was nice. The pool situation was a little awkward as it does appear to be mainly for the bigger house as other reviews stated. The gas grill which is beneath the main house by the pool is communal. The main reason I gave this a 4 was because the smoke alarms in the rental did not have any batteries. Everything else was as described."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Beach nearby
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
9.0 out of 10, Wonderful, 60 reviews
"Overall, its a great location, the communication was key, the stay was fantastic, the house was outdated and a few minor obstacles but we made the BEST of everything. We wanted relaxation and thats what we got. Thank You for your hospitality and comforting home!"
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Ocean/Canal Views 21ft Dock - Venture Out #357
Property grounds
Ocean/Canal Views 21ft Dock - Venture Out #357
8.6 out of 10, Excellent, 7 reviews
"We had a great time and the location was perfect for us. The pool on property was nice and clean. Happy with the house and would stay there again!"
Ocean/Canal Views 21ft Dock - Venture Out #357
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, 34 reviews
"This property is super cute. Convenient for being close to Key West without the price of Key West. We VERY much enjoyed our 3 night stay. Our property (#15) had a little grill outside so we were able to cookout one night of our stay. Make sure you stop at Publix or Winn Dixie before getting there it is a litle trek to get to grocery store. I would also suggest bringing a few extra bath towels, our cottage only had 3 and 4 adults. Most things you would need, pots, pans, silverware, cups, coffee...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Exterior
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, 217 reviews
"My daughter and I stayed in Cudjoe Key to be close to Key West. The location was good. The unit had everything we needed both inside and out. We grilled and cooked which was great. The beds were comfortable. Unfortunately, the weather did not cooperate and excursions were cancelled so we spent more time in Key West than we had planned. But the unit had lots of games and the TV had the tennis channel which was very nice. All in all, it was a good time."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Beachside @ Torchview Waterfront Retreat
On the beach, beach towels
Beachside @ Torchview Waterfront Retreat
9.8 out of 10, Exceptional, 30 reviews
"My wife and I chose this property to spend 10 days celebrating our 30th anniversary. Unbelievable. If you want a getaway spot away from the crazies on Duval Street, but within striking distance, this is the place. If you love nature, this is your place - Key deer, iguanas, amazing water life… Sunset views? Stunning. We also rented a boat to explore for a few days, the dock is such a great part of this property. Condition was stellar, completely as advertised. I’ve seen reviews questioning the...
Beachside @ Torchview Waterfront Retreat
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Beach nearby
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.4 out of 10, Exceptional, 20 reviews
"There is a difference staying at a HomeAway or VRBO property that is a residence versus one that is just an investment property. Coconut Telegraph is an investment property. The location was everything we expected. The rest left a lot to be desired. The magic of staying in Venture Out is that you can step out your back door and jump in the Atlantic Ocean. We couldn't do that at this property, as there was no swim ladder. I also wouldn't want to tie up my boat here. The back concrete deck/dock...
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
One of the very few beach houses with a daily, rental license in the Keys.
Exterior
One of the very few beach houses with a daily, rental license in the Keys.
9.0 out of 10, Wonderful, 48 reviews
"Great place in an unbelievable location. Nice and clean with all the amenities we needed."
The price is CA $816
CA $1,810 total
includes taxes & fees
Jun 16 - Jun 17
One of the very few beach houses with a daily, rental license in the Keys.
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, 65 reviews
"Resorts was great love the pool and water....home was clean nice bedrooms and baths really small but we just sleep in them. Deck was great. To be in early morning watching sun rise..."
Canal front, dockage, 2 bedroom, 2 bath
Cozy, Perfect Conch Cottage!
Pool
Cozy, Perfect Conch Cottage!
9.0 out of 10, Wonderful, 30 reviews
"Our stay was great! The description is accurate. We enjoyed our 6 Mid-March days at "Cozy Perfect Conch Cottage." Yes, it's technically camping, but it's very NICE camping...in a campground...but a very NICE campground. The bed we used (there were only 2 of us) was super comfortable. The WiFi worked great. It was awesome having a full kitchen and washer/dryer. The towels were plentiful, soft and luxurious. Linens were also very soft and comfortable. Everything needed for basic cooking was...
Cozy, Perfect Conch Cottage!
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Property grounds
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
10.0 out of 10, Exceptional, 196 reviews
"Love renting in this little complex but this unit in particular was immaculately maintained. Great communication with the owners and a fantastic location if youre looking for quick access to the ocean. We booked this place for a guys fishing trip and it was much more than we needed (in a good way). Families would have a ton of fun here as well with the pool, kayaks, etc. Cant wait to come back!"
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Don't see what you're looking for?
See all available properties in Summerland Key
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.

Summerland Key Vacation Rental Travel Info

Number of vacation rentals
20
Popular accommodation
Summerland Key private vacation homes
Known landmarks
Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market
International airports
Miami, FL (MIA-Miami Intl.) and Key West, FL (EYW-Key West Intl.)

Other types of properties in Summerland Key you may be interested in

Sugarloaf Key Hotel at KOA Resort
Private beach, snorkeling, kayaking, motor boating
Sugarloaf Key Hotel at KOA Resort
2.0 star property
9.8 out of 10, Exceptional, 163 reviews
"Great location, spacious suite, very clean, would stay here again"
Sugarloaf Key Hotel at KOA Resort
Parmer's Resort
View from property
Parmer's Resort
2.5 star property
8.8 out of 10, Excellent, 1,001 reviews
"The people are very nice and the view was beautiful. We had a waterfront room. The onky issue is the bathroom is very outdated and the grout/shower shows it. I can look past it because its clean but others may not."
The price is CA $217
CA $289 total
includes taxes & fees
Jun 24 - Jun 25
Parmer's Resort
Sugar Loaf Lodge
Balcony
Sugar Loaf Lodge
2.5 star property
8.0 out of 10, Very good, 1,006 reviews
"Good 👍 "
The price is CA $230
CA $259 total
includes taxes & fees
Jun 10 - Jun 11
Sugar Loaf Lodge
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.

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Summerland Key vacation rentals we have selected for you start as low as CA $477 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 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?

Gated Community on Open Water with Dock, Heated 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. You can relax into your vacation with a garden and a selection of games. Some other top choices in Summerland Key are Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West and Old Florida Style, wrap around porch, boat basin for dockage, open water.

How many vacation rentals are there in Summerland Key?

Choose from 453 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.

Recent reviews of Summerland Key properties
Expedia verified reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

5/5 Excellent
"Great location, spacious suite, very clean, would stay here again"
A verified traveller stayed at Sugarloaf Key Hotel at KOA Resort
Posted 4 days ago
Sugarloaf Key Hotel at KOA Resort