Summerland Key Vacation Rentals

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Vacation Rentals in Summerland Key

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (90)
"Good place. 3 bed rooms all with Queen size beds. It was perfect for us. We sat on the porch mostly when we were there and played games. Not a long ride to Key West. Overall- we were happy and would stay there again."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, (45)
"Great stay! Enjoyed location and property. Just a heads up may have an electrical issue in kitchen and small bedroom with electrical outlets. We had a blast other than that. Would recommend staying."
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
9.8 out of 10, Exceptional, (186)
"Highly recommend"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (53)
"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
Cozy, Perfect Conch Cottage!
9.0 out of 10, Wonderful, (30)
"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!
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (204)
"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 $479
CA $604 total
includes taxes & fees
Jun 18 - Jun 19
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (217)
"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
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, (12)
"What a beautiful home. Great views of the ocean and the sunrises were amazing. Neighbors were awesome and fun to talk to. just an incredible place."
LICENSE TO CHILL ~ 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.
9.0 out of 10, Wonderful, (48)
"Great place in an unbelievable location. Nice and clean with all the amenities we needed."
The price is CA $822
CA $1,822 total
includes taxes & fees
Jun 16 - Jun 17
One of the very few beach houses with a daily, rental license in the Keys.
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
10.0 out of 10, Exceptional, (26)
"Easy from start to finish! Lovely cottage in very central location in the Florida Keys. Hope was the highlight of the trip, truly the “hostess with the mostest.” She checked in daily, offered great tips for restaurants and activities. Loved everything about the property: quiet, the outdoor shower, the beds, the pool, Lulu, and the freshest seafood! Would definitely recommend."
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
10.0 out of 10, Exceptional, (14)
"Excellent concept. Loved this unit. Very clean. Only had one small glitch when checking in because I don't text. The lady who manages the unit was exceptional. Wished I could find employees like her."
Little Gem in Paradise, with Terrace & Private Patio in Resort with Amenities.
Springs Venture Out Dolphin House (#386) with beautiful open water views
9.4 out of 10, Exceptional, (80)
"The location was great, right on the water with a great view. The house and amenities were perfect for us."
Springs Venture Out Dolphin House (#386) with beautiful open water views
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.2 out of 10, Very good, (26)
"Cottage is very nice, old but well maintained. Entrance difficult to find."
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
9.0 out of 10, Wonderful, (60)
"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
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, (34)
"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
Beachside @ Torchview Waterfront Retreat
9.8 out of 10, Exceptional, (30)
"Great view, quiet location."
Beachside @ Torchview Waterfront Retreat
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.4 out of 10, Exceptional, (20)
"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!
Waterfront Home
8.8 out of 10, Excellent, (141)
"Would definitely come back!!!!"
Waterfront Home
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
9.6 out of 10, Exceptional, (169)
"I had a wonderful 2 week stay. It was better than advertised and the view off the back porch is indescribably beautiful. I had friends fly in and out of Key West with no problems. Only a 30min drive. We fished,snorkeled,ate delicious food,and watched the most gorgeous sunrises. Overflow parking and check-in were handled professionally by the security team. The unit was clean,spacious,and roomy for its size. I will definitely be back We nicknamed the back porch "Paradise Porch"."
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Enjoy Caribbean weather. Last minute opening beginning 5/28/24! Enjoy the Keys!
9.4 out of 10, Exceptional, (125)
"Great stay. Comfy beds. Everything you need."
Enjoy Caribbean weather. Last minute opening beginning 5/28/24! Enjoy the Keys!
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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

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

Sugarloaf Key Hotel at KOA Resort
2.0 star property
9.8 out of 10, Exceptional, (161)
"Great!"
Sugarloaf Key Hotel at KOA Resort
Parmer's Resort
2.5 star property
8.8 out of 10, Excellent, (1000)
"Beautiful and we liked the chairs on the porch to relax and enjoy the quiet "
The price is CA $218
CA $290 total
includes taxes & fees
Jun 18 - Jun 19
Parmer's Resort
Sugar Loaf Lodge
2.5 star property
8.0 out of 10, Very good, (1001)
"We loved the wildlife habitat area around the property only thing we were disappointed in is not being able to fish."
The price is CA $231
CA $260 total
includes taxes & fees
Jun 2 - Jun 3
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.

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?

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.

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