Summerland Key Holiday Rentals

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Holiday Rentals in Summerland Key

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, (193)
"Love the location. Great little gated neighborhood. KW is an easy drive and there is a lot to do in the immediate area. Would definitely stay again."
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Property grounds
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
10.0 out of 10, Exceptional, (2)
"This is a nice property. The accommodations were large enough for my family. The indoor space was clean and nicely appointed. The outdoor space was ok. Due to how close the units are together you are right next to your neighbors car when sitting on the patio. The location is about 20 miles from Key West allowing for easy day trips while resting in a quieter location. I would definitely stay here again."
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Waterfront Beach House with Dock & Heated Pool!
Fridge, microwave, oven, stovetop
Waterfront Beach House with Dock & Heated Pool!
10.0 out of 10, Exceptional, (68)
"Wasnt sure on reclining process"
Waterfront Beach House with Dock & Heated Pool!
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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, (201)
"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 AU$684
per night
13 May - 14 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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, (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
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, (180)
"very well stocked and clean, Will be back for sure"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
Beach
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
9.8 out of 10, Exceptional, (165)
"Relaxing and beautiful!"
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
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, (43)
"This property is awesome!! Great location! Had a blast on the porch and paddle boarding from the front lagoon. Only issue was the AC leaked in ceiling and master bedroom bc we turned them down too low. This should be noted on house rules to avoid it happening to future renters. Other than that small issue I would love to return and stay here again ASAP. Thank you Susan for your hospitality!"
Old Florida Style, wrap around porch, boat basin for dockage, open water
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Pool
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
9.8 out of 10, Exceptional, (98)
"The location is perfect to airport and Key West/Marathon. We found the house to have everything we needed and the neighborhood was peaceful and beautiful."
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
A heated pool
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
9.6 out of 10, Exceptional, (168)
"Stayed with another couple and thoroughly enjoyed the cottage. The porch is an awesome place to enjoy your morning coffee and the dock is an even better place to enjoy the sunset and a glass of wine! The property has all the amenities for a great vacation."
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
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, (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
Casa Del Mar in Venture Out Unit 253
Property grounds
Casa Del Mar in Venture Out Unit 253
9.6 out of 10, Exceptional, (18)
"Enjoyed stay at this property, loved all the amenities. Distances to different Islands were Good. Lots of good food and things to do."
Casa Del Mar in Venture Out Unit 253
Gulf-front house near Key West with private beach & pool - snowbird-friendly
A heated pool
Gulf-front house near Key West with private beach & pool - snowbird-friendly
9.6 out of 10, Exceptional, (33)
"This house is stunning and very secluded. We were there four nights to celebrate a friends 40th birthday and it did not disappoint. Four adult couples and a baby and we each had our own room with bathrooms within. The sunset from the pool was unbelievable each night. We swam, used kayaks and floated in ocean. If you plan to walk into ocean from private beach I would recommend water shoes. We did not utilize the game room because we had perfect weather and spent the whole trip outside around...
Gulf-front house near Key West with private beach & pool - snowbird-friendly
Comfortable Waterfront Vacation Rental
Sun-loungers, beach towels
Comfortable Waterfront Vacation Rental
9.4 out of 10, Exceptional, (136)
"Right price for location 35 minutes from Key West."
Comfortable Waterfront Vacation Rental
Tropical Getaway in Paradise.
Outdoor pool, a heated pool
Tropical Getaway in Paradise.
9.4 out of 10, Exceptional, (79)
"The property was everything it said in the listing. It was clean, comfortable and a grest place to sit and relax after a day full of adventures. We were visiting our son who lives on Summerland Key and works for the Boy Scouts. It was centrally located so we could go east or west and explore. Thanks for making this trip enjoyable, and relaxing. Sincerely, the Meyers'"
Tropical Getaway in Paradise.
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool
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
Outdoor dining
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.2 out of 10, Wonderful, (173)
"Wonderful location and community. Enjoyed the ping pong, tennis & pickleball! Bikes & kayaks would have been great. The house was comfortable and cute. Had to call host for a repair and was taken care of within an hour. Cleanliness could have been better - dusty and cabinets/drawers could use attention. Very happy with our stay."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Cozy, Perfect Conch Cottage!
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!
SEA SHELL COTTAGE UNIT #2
Beach
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
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, (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.
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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 Holiday Home Travel Info

Number of holiday homes
20
Popular accommodation
Summerland Key private holiday 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, snorkelling, kayaking, motor boating
Sugarloaf Key Hotel at KOA Resort
2.0 star property
9.8 out of 10, Exceptional, (126)
"The unit was clean and recently updated. We had a view of the water. It is about 20 minutes north of Key West. They have a beach area, swimming pool, hot tub, and cafe onsite. "
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, (1001)
"This is a nice little group of older buildings right on Little Torch Key. Not too fancy but you have a pool, some little piers and even a boat launch. This is not ocean it's water between keys so no surf and mostly coral but a little sand on their beach for getting feet wet. Staff is friendly, they have laundry and a nice little continental breakfast with fresh fruit. Great location for seeing other keys (26 mi to key west) If you really want a beach just 5 miles to one at a state partk and nice...
The price is AU$261
per night
15 May - 16 May
Parmer's Resort
Sugar Loaf Lodge
Balcony
Sugar Loaf Lodge
2.5 star property
8.0 out of 10, Very good, (1001)
"We have a wonderful stay quite and super nice"
The price is AU$291
per night
5 May - 6 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.

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 favourite 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 depend 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 AU$684 per night. Entering your travel dates in the search wizard might find you 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?

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

Looe Key Reef Resort

Looe Key Reef Resort

5/5 Excellent
"Loved the location of this property. Lower keys with easy access to Key West, Marathon and all the Keys. Restaurant and Dive shop provide all the necessities for the fun adventurer. Staff is very kind and helpful. The hotel rooms are nice and Old Florida. Your rooms back door opens to the water canal for great views. It's not the Ritz and neither is the price. Love this place and took a swim in the pool to cool off. Worth every penny for it's location and snorkel and dive options. Take full advantage of the restaurant... bands were good. "
A verified traveller stayed at Looe Key Reef Resort
Posted 3 days ago
Looe Key Reef Resort