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Summerland Key Vacation Rentals

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Vacation Rentals in Summerland Key

Kelly's Kabin Private Cottage on Summerland Key

Kelly's Kabin Private Cottage on Summerland Key

Summerland Key, FL
The price is $250 per night from Aug 13 to Aug 13
Situated in Summerland Key, this cottage is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor Center. Lower ...
4.8/5Exceptional! (31 reviews)
Cute Kottage
"Excellent communication from owner. Always answered any questions right away. Had a couple small issues and they were take. Care of right away."

Reviewed on Jul 8, 2021

Kelly's Kabin Private Cottage on Summerland Key
Waterfront, Two-story House W/private Outdoor Pool, Poolside Grill, Boat Access

Waterfront, Two-story House W/private Outdoor Pool, Poolside Grill, Boat Access

Summerland Key, FL
Situated on the waterfront, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor Center. ...
4/5Very Good! (1 review)
Met expectations
"Positives: Spacious comfortable house. Perfect for the family. Very clean and nicely appointed with furniture. Pool and spa were a big hit with children and adults alike. Nice boat slip, but you need to rent your own kayaks, paddle boards, etc. Screen door is in bad need of replacement and only one ..."

Reviewed on Jan 15, 2021

Waterfront, Two-story House W/private Outdoor Pool, Poolside Grill, Boat Access
Summerland Breeze - A Resort Style Three House Retreat

Summerland Breeze - A Resort Style Three House Retreat

Summerland Key, FL
This family-friendly Summerland Key vacation home is located on the waterfront, 2.4 mi (3.9 km) from Upper Sugarloaf Sound, and within 9 mi (15 km) of Upper ...
Summerland Breeze - A Resort Style Three House Retreat
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New Listing! Summerland Canal-front Escape W/ Pool 2 Bedroom Home

New Listing! Summerland Canal-front Escape W/ Pool 2 Bedroom Home

3.5 out of 5
138 Airport Dr S, Summerland Key, FL
Situated in Summerland Key, this golf vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, National Key Deer Refuge Visitor Center, and Upper Sugarloaf ...
New Listing! Summerland Canal-front Escape W/ Pool 2 Bedroom Home
Forever Summer

Forever Summer

Summerland Key, FL
Situated on the waterfront, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor Center. ...
Forever Summer
Blue Pearl of Summerland Key

Blue Pearl of Summerland Key

Summerland Key, FL
Situated on the waterfront, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor Center. ...
5/5Exceptional! (1 review)
First Class!
"This is a beautiful , well appointed home in a great location. John was a wonderful host who went out of his way to provide everything we needed for our month in the Keys. His local recommendations were very helpful when it came to dining out, renting a boat and booking an offshore fishing excursion ..."

Reviewed on Mar 11, 2021

Blue Pearl of Summerland Key
Charming and Private

Charming and Private

Summerland Key, FL
Situated on the waterfront, this vacation home is within 12 mi (20 km) of Upper Sugarloaf Key, National Key Deer Refuge Visitor Center, and No Name Key. Upper ...
4.5/5Wonderful! (4 reviews)
Wonderful break from the hustle
"Very much enjoyed property and our stay. It was exactly as advertised. We rented a boat for the entire stay. Docked it the canal in back. What more can you ask for? Ocean, boating, pool, home, everything you need for a islands paradise. Owner is very easy to work with. Hope to go and stay again. ..."

Reviewed on Jul 4, 2021

Charming and Private
Open Ocean View Summerland Key

Open Ocean View Summerland Key

Summerland Key, FL
Located on the waterfront, this family-friendly vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and No Name Key. Lower Sugarloaf ...
4.8/5Exceptional! (4 reviews)
Paradise!!
"If I could give this property more than 5 stars I would. This was truly paradise, the pool, the views, the fishing off the dock, the kayaking - everything was so worth it. Dealing with the owner was great, he was so accommodating, so helpful and so understanding of whatever we needed. To say that ..."

Reviewed on Apr 13, 2020

Open Ocean View Summerland Key
++++perfect Keys Pool Home, Minutes TO KEY West, Convenient TO Everything++++

++++perfect Keys Pool Home, Minutes TO KEY West, Convenient TO Everything++++

Summerland Key, FL
Situated on the waterfront, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, National Key Deer Refuge Visitor Center, and Upper Sugarloaf Sound. ...
5/5Exceptional! (14 reviews)
Awesome house and location!
"The house had everything we needed and the pool was great! The location was close enough to Key West and great Fishing!"

Reviewed on Aug 13, 2018

++++perfect Keys Pool Home, Minutes TO KEY West, Convenient TO Everything++++
3 Bedroom Accommodation in Summerland Key

3 Bedroom Accommodation in Summerland Key

Summerland Key, FL
Situated in Summerland Key, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor Center. ...
3 Bedroom Accommodation in Summerland Key
Deep/wide/flow-though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise

Deep/wide/flow-though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise

Summerland Key, FL
Located on the beach, this family-friendly vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor ...
4.9/5Exceptional! (21 reviews)
Wonderful Stay!
"We enjoyed the house and property! Luke was super responsive and the house was everything we expected. We parked our boat out back and were able to get to all the reefs and locations we wanted in a timely manner. Plenty of sleeping places for our entire family. The kitchen was well stocked. The bikes ..."

Reviewed on Jul 20, 2021

Deep/wide/flow-though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
Canal Front With Lots Of Parking Space

Canal Front With Lots Of Parking Space

Summerland Key, FL
Situated on the waterfront, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, National Key Deer Refuge Visitor Center, and Upper Sugarloaf Sound. ...
4.9/5Exceptional! (16 reviews)
Great Place to Stay
"We loved staying at Craig's place on Summerland Key. Was great having a place to park my boat/Trailer on property (lots of room for parking). Right on a swimming canal which gave access to offshore or back country. Also since I love aviation and having a daytime runway right out the front door was ..."

Reviewed on May 4, 2021

Canal Front With Lots Of Parking Space
Pool Home on Tranquil Private Cruikshank Island

Pool Home on Tranquil Private Cruikshank Island

Summerland Key, FL
Situated on the waterfront, this romantic vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and National Key Deer Refuge Visitor ...
5/5Exceptional! (6 reviews)
Greatly exceeded our expectations!
"While the pictures of the house look amazing on the VRBO website, they do not convey how beautiful this house really is! Brian and Marion have a lovely home that has the most incredible views of the Florida sunsets. The kitchen is very well equipped and had everything we needed. We would gladly repeat ..."

Reviewed on Feb 11, 2021

Pool Home on Tranquil Private Cruikshank Island
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

2 out of 5
38801 Overseas Highway, Big Pine Key, FL
Nestled on the beach, this Big Pine Key campground is within a 10-minute walk of Bahia Honda State Park and Sandspur Beach. Loggerhead Beach is 2.2 mi (3.6 km) ...
4.3/5Excellent! (90 reviews)
"The location is convenient if you would like to visit Key West for the day or spend some time in Marathon."

Reviewed on Jul 11, 2021

Sunshine Key RV Resort & Marina
True Paradise: Luxury Marina- Summer Special Rates

True Paradise: Luxury Marina- Summer Special Rates

Key West, FL
The price is $174 per night from Aug 4 to Aug 4
Situated on the waterfront, this historic houseboat is 0.6 mi (1 km) from Robbie's and 1.6 mi (2.7 km) from Key West Harbour. Key West Golf Club and Lower Keys ...
5/5Exceptional! (6 reviews)
Loved It!!!!!
"The boat was beautiful. We were comfortable and enjoyed our stay. Everything was great!!!!"

Reviewed on Jul 15, 2021

True Paradise: Luxury Marina- Summer Special Rates
Waterfront Cozy Cottage With Boat Ramp & Dock!

Waterfront Cozy Cottage With Boat Ramp & Dock!

Little Torch Key, FL
This family-friendly Little Torch Key cottage is located on the waterfront, 2.5 mi (4 km) from National Key Deer Refuge Visitor Center, and within 9 mi (15 km) ...
4.8/5Exceptional! (21 reviews)
Private Slice of Paradise
"Location Location Location!!! Incredible cozy cottage on the water, the pier was magical day and night, crystal clear water. Dream Spot!!! My entire family was awe struck with the views and the location on Little Torch was perfect for doing things throughout the keys , short ride to Key West, Bahia ..."

Reviewed on May 7, 2021

Waterfront Cozy Cottage With Boat Ramp & Dock!
Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 mi Beach

Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 mi Beach

Key West, FL
This family-friendly Key West vacation home is located near the beach, within 1 mi (2 km) of Lower Keys Medical Center and Key West Harbour. Key West Golf Club ...
5/5Exceptional! (226 reviews)
Very nice property!
"We initially thought the location of this property off the main island of Key West would be a negative, but especially for a family, we ended up thinking that having a quieter, less crazy neighborhood for our stay was better. Having access to the pool on the property was a plus as well, especially ..."

Reviewed on Jul 26, 2021

Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 mi Beach
Blue Chill Vacation!!!

Blue Chill Vacation!!!

Cudjoe Key, FL
Situated in Cudjoe Key, this property is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Lower Sugarloaf Sound. Saddlebunch Keys and National ...
Blue Chill Vacation!!!
Shaded 2B / 1B Midrise With Canal Views

Shaded 2B / 1B Midrise With Canal Views

Cudjoe Key, FL
Situated in Cudjoe Key, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Lower Sugarloaf Sound. Saddlebunch Keys ...
4.3/5Excellent! (8 reviews)
Great place to get together!
"Easy. Maps could be clearer. Felt very safe. Connected with long time friends and a former colleague. Will return."

Reviewed on Jul 15, 2021

Shaded 2B / 1B Midrise With Canal Views
Moonlight Bay - Beautiful Newer Beneteau 38 in Key West Florida

Moonlight Bay - Beautiful Newer Beneteau 38 in Key West Florida

Key West, FL
Situated on the waterfront, this houseboat is 0.6 mi (1 km) from Robbie's and 1.6 mi (2.7 km) from Key West Harbour. Key West Golf Club and Lower Keys Medical ...
4.7/5Exceptional! (10 reviews)
"Boat was great. Very clean and neat. Wish we were told about parking, because we ended up getting towed which cost me an extra $300."

Reviewed on Jul 14, 2021

Moonlight Bay - Beautiful Newer Beneteau 38 in Key West Florida
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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.

Large Group Rentals Summerland Key

Modern Keys

Modern Keys

3.5 out of 5
10 Shoreline Rd., Key West, FL
Modern Keys
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, condos, resorts, cabins, villas, motels. 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. is the cheapest month to visit, with the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Summerland Key vacation rentals range between $174 per night and $250 per night.

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. 

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