Summerland Key Vacation Rentals

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Vacation Rentals in Summerland Key

Canal front, dockage, 2 bedroom, 2 bath
9.2 out of 10, Wonderful, (63)
"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
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.2 out of 10, Wonderful, (174)
"Great location, 23 miles to Key West. View from deck is breathtaking."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Waterfront Home
8.8 out of 10, Excellent, (141)
"Would definitely come back!!!!"
Waterfront Home
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Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (89)
"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
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (182)
"Very nice"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (202)
"The property and townhouse were all very nice. If your wanting to go to Key West multiple times during the week, this location is a quick 21 miles. Townhouse was very accommodating for two couples. Pool and tiki patio areas were all clean, plenty of seating, and quiet. Only con would be bicycles need attention due to flat tires. We would book this property in the future."
The price is CA $479
CA $607 total
includes taxes & fees
May 29 - May 30
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
9.8 out of 10, Exceptional, (167)
"The resort was well kept and the security team was very welcoming and helpful. We stayed right on the water and had a great time."
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (216)
"Beautiful house in a gated community. Comfortable beds and a well stocked kitchen. 35 min to Key West, close to beaches and great restaurants nearby. We would not hesitate to stay here again!"
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Cozy, Perfect Conch Cottage!
9.2 out of 10, Wonderful, (29)
"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!
One of the very few beach houses with a daily, rental license in the Keys.
9.0 out of 10, Wonderful, (47)
"Layout of house and location are perfect. The owners were very communicative and responsive."
One of the very few beach houses with a daily, rental license in the Keys.
Cudjoe Key, FL RV Resort RV Lot
8.0 out of 10, Very good, (4)
"Had a wonderful stay"
The price is CA $130
CA $173 total
includes taxes & fees
May 14 - May 15
Cudjoe Key, FL RV Resort RV Lot
Oceanfront home with private pool, boat dock, kayaks, and private beach
9.4 out of 10, Exceptional, (72)
"My husband and I enjoyed the view this home has. They had everything we needed...access to the water, kayaks, grill, pleanty of towels, coconuts (fall from the tree make for an extra treat our son had so much fun with). It was a nice retreat close enough to Key West. This place had great outdoor space, very relaxing and a fun place to be."
Oceanfront home with private pool, boat dock, kayaks, and private beach
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
9.6 out of 10, Exceptional, (168)
"Property and property owner were great. Nice quiet place for relaxation."
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Enjoy Caribbean weather. Last minute opening beginning 5/2/24! Enjoy the Keys!
9.4 out of 10, Exceptional, (124)
"Great stay. Comfy beds. Everything you need."
Enjoy Caribbean weather. Last minute opening beginning 5/2/24! Enjoy the Keys!
SEA SHELL COTTAGE UNIT #2
9.2 out of 10, Wonderful, (7)
"Nice, quiet, relaxing, reasonably priced with a lovely pool outside our door!"
SEA SHELL COTTAGE UNIT #2
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
10.0 out of 10, Exceptional, (25)
"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
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
9.2 out of 10, Wonderful, (90)
"Location and outdoor living space was awesome!"
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
9.6 out of 10, Exceptional, (38)
"Relaxed property away from the hub of key west. Access to everything the keys has to offer with your own little slice of heaven at the end of day. Excellent host and communication. Already planning next years trip!!"
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
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
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.8 out of 10, Exceptional, (17)
"This place was awesome!! Plenty of space, beautiful location. Very clean. Great place to hang out and fish/ paddle board. Loved the nice chair/ rockers underneath to hang out. Camp ground is always great and this was a very nice location. 4 stayed but 6 of us hung out there both evenings and had a great time. Would definitely recommend"
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
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

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, (137)
"What I liked was the suite it was nice and clean. Did not care for the narrowness of the parking space."
Sugarloaf Key Hotel at KOA Resort
Parmer's Resort
2.5 star property
8.8 out of 10, Excellent, (1001)
"Everything was perfect!! I will recommend to all my friends and family…"
The price is CA $180
CA $248 total
includes taxes & fees
May 27 - May 28
Parmer's Resort
Sugar Loaf Lodge
2.5 star property
8.0 out of 10, Very good, (1003)
"The view from our room was awesome tiki bar was not open when we were there and restaurant on property was very expensive "
The price is CA $231
CA $260 total
includes taxes & fees
May 14 - May 15
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.

Recent reviews of Summerland Key properties
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