Summerland Key Holiday Rentals

Holiday Rentals in Summerland Key

Balcony
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
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, (45)
"We brought a boat with us. The protected bay is perfect with a marked channel (note it is a tight turn to get in during high winds with shallow spots). Plenty of room for a trailer. The view here is very peaceful and we loved sitting out on the break-wall. We all slept comfortable and appreciated that each room had their own AC unit for control. The restaurant that is walking distance had great food, drinks, and live music. Minor thing, but my group wanted it passed along that the toaster needs...
Old Florida Style, wrap around porch, boat basin for dockage, open water
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (185)
"Highly recommend"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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Fridge, microwave, oven, stovetop
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
Pool
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!
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (204)
"Overall, a very nice property in a good location, with good amenities. Located near several good Restaurants, especially the Square Grouper. Communication with Host was very good."
The price is NZ$725
per night
30 May - 31 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Exterior
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
Property grounds
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!
Exterior
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 NZ$2,170
per night
28 May - 29 May
One of the very few beach houses with a daily, rental license in the Keys.
Sun-loungers, beach towels
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
A heated pool
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.
Outdoor pool, a heated pool
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
Beach nearby
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
Beach nearby
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
Beach
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
On the beach, beach towels
Beachside @ Torchview Waterfront Retreat
9.8 out of 10, Exceptional, (28)
"Great view, quiet location."
Beachside @ Torchview Waterfront Retreat
Beach nearby
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, (19)
"We absolutely loved our stay at Coconut Telegraph! We plan to return next year. The place is even better than described on VRBO and it is LITERALLY on the beautiful aqua blue water! The pool is plenty big and we enjoyed the tiki huts along the shoreline. The security team does an excellent job. It was very quiet at night. Easy drive to Key West if that is of interest. We did not use the concierge service so cannot comment except to say they had a lot to offer! Local restaurants are excellent. If...
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Exterior
Waterfront Home
8.8 out of 10, Excellent, (141)
"Would definitely come back!!!!"
Waterfront Home
A heated pool
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
Beach
Enjoy Caribbean weather. Last minute opening beginning 5/19/24! Enjoy the Keys!
9.4 out of 10, Exceptional, (124)
"Great stay. Comfy beds. Everything you need."
Enjoy Caribbean weather. Last minute opening beginning 5/19/24! 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.

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

Private beach, snorkelling, kayaking, motor boating
Sugarloaf Key Hotel at KOA Resort
2.0 star property
9.8 out of 10, Exceptional, (154)
"Stayed for a business trip and it was clean, comfortable, the staff is very friendly, a beautiful unit with a big balcony to relax and have a nice breakfast, lunch, or dinner, with comfy chairs and spacious table. The bathroom was updated as well as the whole unit. Very big and clean! We took our fur babies and there is a cute park for them to just roam around, or do some obstacle courses. Very clean and convenient. There is also a big heated pool with a jacuzzi, live music and a...
Sugarloaf Key Hotel at KOA Resort
View from property
Parmer's Resort
2.5 star property
8.8 out of 10, Excellent, (1002)
"Beautiful and we liked the chairs on the porch to relax and enjoy the quiet "
The price is NZ$293
per night
3 Jun - 4 Jun
Parmer's Resort
Balcony
Sugar Loaf Lodge
2.5 star property
8.0 out of 10, Very good, (1004)
"Very nice place to stay, only about 30 minutes from Key West. Nice view from the balcony. And my favorite part? Nearly instant hot water in the shower!"
The price is NZ$311
per night
28 May - 29 May
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Summerland Key holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Summerland Key. 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 Summerland Key. 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 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 holiday 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 Summerland Key short-term rentals, that won’t be hard to do.

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?

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes: This highly rated holiday home rental in Summerland Key is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday 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 holiday rentals are there in Summerland Key?

Choose from 453 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.

Recent reviews of Summerland Key properties
Expedia verified reviews

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.

5/5 Excellent
Keys Fishing Trip
"Great place in an unbelievable location. Nice and clean with all the amenities we needed."
A verified traveller stayed at One of the very few beach houses with a daily, rental license in the Keys.
Posted 1 day ago
One of the very few beach houses with a daily, rental license in the Keys.