Search Vacation Homes in Summerland Key

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Browse Select Summerland Key Vacation Homes

3 BEDROOM BEACH HOUSE CLOSE TO BEACH & KEY WEST
The price is $299 per night from Sep 27 to Sep 27
Located in Sands, this historic vacation home is 0.9 mi (1.4 km) from National Key Deer Refuge Visitor Center and within 6 mi (10 km) of No Name Key and Cook ...
4.2/5Excellent! (14 reviews)
Great Stay on Short Notice!
"Jesus was in constant communication and helped us with a 2 night stay on very short notice. Highly recommend!"

Reviewed on Jul 26, 2021

3 BEDROOM BEACH HOUSE CLOSE TO BEACH & KEY WEST
Walk to  Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Located on the waterfront, this family-friendly vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Lower Sugarloaf Sound. ...
4.7/5Exceptional! (22 reviews)
Perfect keys home
"This house was equipped with everything we needed to enjoy our extra long weekend. Very clean & the added extras was a plus. The boat dock has new rub rails which was a plus with our 23 foot boat. The outdoor patio had comfortable seating which allowed us to view the beautiful sunsets. We will def. ..."

Reviewed on Sep 7, 2021

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Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Lower Keys paradise
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. National Key Deer ...
5/5Exceptional! (3 reviews)
Lovely!
"Really nice property. Inside of the house is awesome. Way better than expected. Full kitchen and amenities. However the only draw back is the internet connection. But we were out anyways."

Reviewed on Sep 3, 2021

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Lower Keys paradise
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**OCTOPUS'S GARDEN @ CORAL HAMMOCK** Spacious Home & Pool + LAST KEY SERVICES...
Situated by the sea, this historic vacation home is within 1 mi (2 km) of Lower Keys Medical Center, Key West Golf Club, and Key West Harbour. Robbie's and Fort ...
4.9/5Exceptional! (47 reviews)
Bachelor Weekend
"Fishing. Duval. Pool. Key West in General for Bachelor Weekend"

Reviewed on Aug 27, 2021

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**OCTOPUS'S GARDEN @ CORAL HAMMOCK** Spacious Home & Pool + LAST KEY SERVICES...
4br/4.5ba - 2,402 interior sq ft
Situated in Key West, this vacation home is 0.7 mi (1.1 km) from Key West Golf Club and 1.8 mi (2.9 km) from Key West Harbour. Lower Keys Medical Center and ...
5/5Exceptional! (6 reviews)
Great place to stay in Key West
"Love the pool, clean property, great experiences. Will come back if I would have to make another trip to Key West!"

Reviewed on Sep 14, 2021

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4br/4.5ba - 2,402 interior sq ft
Coral Hammock Poolside Home: 3  BR, 3  BA House in Key West, Sleeps 6
Situated in Key West, this vacation home is within 1 mi (2 km) of Lower Keys Medical Center and Key West Harbour. Key West Golf Club and Robbie's are also within ...
4.9/5Exceptional! (28 reviews)
Loved it
"We loved the place!"

Reviewed on Aug 9, 2021

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Coral Hammock Poolside Home: 3 BR, 3 BA House in Key West, Sleeps 6
Casa Cove Beautiful Tropical Decorated 3 KING SUITES  Sleeps 8  Pool 2 mi  beach
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! (106 reviews)
Vacay
"This place was exactly as it was described. Great and friendly host! I would definitely stay there again."

Reviewed on Sep 15, 2021

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Casa Cove Beautiful Tropical Decorated 3 KING SUITES Sleeps 8 Pool 2 mi beach
Key Haven Estates' "Nautical Splender"; 5br/5.5ba - 2,836 interior sq ft
Situated on the waterfront, this vacation home is 0.7 mi (1.1 km) from Key West Golf Club and 1.8 mi (2.9 km) from Key West Harbour. Lower Keys Medical Center ...
5/5Exceptional! (10 reviews)
Bachelorette party
"We loved our stay! Great house for a big group of people- quick ride to down town key west. We loved the pool and open living space! Highly recommend if you have a large group!"

Reviewed on Sep 13, 2021

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Key Haven Estates' "Nautical Splender"; 5br/5.5ba - 2,836 interior sq ft
Upcoming openings!!!
Cudjoe Key, FL
Set in Cudjoe Key, this family-friendly vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Lower Sugarloaf Sound. Sugarloaf ...
4.6/5Exceptional! (54 reviews)
Fantastic!
"Everything was great! House was clean and comfy! Pool and atmosphere a 10 out of 10!"

Reviewed on Aug 31, 2021

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Upcoming openings!!!
VO # 135- 2/2 Resort with Ocean View, Venture out #135
Located on the waterfront, this family-friendly vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Lower Sugarloaf Sound. ...
4.9/5Exceptional! (7 reviews)
Cudjoe key
"Fantastic"

Reviewed on Aug 27, 2021

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VO # 135- 2/2 Resort with Ocean View, Venture out #135
Key Haven Estates' "Classic Elegance"; 4br, 4.5 bath 2,331 sq ft
Situated on the waterfront, this vacation home is within 2 mi (3 km) of Lower Keys Medical Center, Key West Golf Club, and Saddlebunch Keys. Key West Harbour ...
4.8/5Exceptional! (9 reviews)
Perfect location
"We spent 7 days at this property and still was not ready to go home ! The bedrooms are all spades nicely apart and accommodated our group of seven nicely ! They were able to convert one of the twin bed rooms into a kind which was perfect ! The house was very clean and new ! No left over items from ..."

Reviewed on Sep 14, 2021

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Key Haven Estates' "Classic Elegance"; 4br, 4.5 bath 2,331 sq ft
 Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
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! (235 reviews)
Excellent place to stay, such a good/safe area. We had a blast!
"Awesome/safe location and only a 10 minute Uber ride to duval street (and that’s with traffic). We went for my boyfriends 25th birthday and needless to say we thoroughly enjoyed being able to come home with such a roomy place to stay. Check in was the most easy I’ve ever experienced and Judy gives ..."

Reviewed on Sep 13, 2021

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Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
Dog-Friendly Resort Community Home w/ a Shared Pool, Hot Tub, & Tennis Court
Situated by the sea, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Lower Sugarloaf Sound. National Key Deer Refuge ...
4.2/5Very Good! (10 reviews)
Family vacay
"We had a great time. The complex was nice and the accommodations were good and as described with a couple of issues. Will definitely consider returning to this location sometime in the future."

Reviewed on Sep 6, 2021

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Dog-Friendly Resort Community Home w/ a Shared Pool, Hot Tub, & Tennis Court
Just 20 miles from Key West!  Oceanfront, dockage, kayaks, swimming pool
Located in Cutthroat Harbor Estates, this historic vacation home is 3.1 mi (5 km) from Upper Sugarloaf Key and within 9 mi (15 km) of Upper Sugarloaf Sound and ...
4.2/5Excellent! (48 reviews)
Relaxing, low-key spot
"Ideal for our purposes: flats boat, in the Keys to fish and lobster with a small group of friends"

Reviewed on Sep 17, 2021

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Just 20 miles from Key West! Oceanfront, dockage, kayaks, swimming pool
Palms Resort at Sugarloaf - Grey House
Situated on the beach, this vacation home is within 1 mi (2 km) of Sugarloaf Beach and Saddlebunch Keys. Lower Sugarloaf Sound and Upper Sugarloaf Sound are ...
3.8/5Good! (5 reviews)
Beautiful property, unbeatable views
"Property was excellent, extremely clean, beds very comfortable, well furnished and well equipped! Manager and caretaker were extremely responsive and went the extra mile to be of service. We did get a tide that brought seaweed in but caretaker made sure to take care of it ASAP. We thoroughly enjoyed ..."

Reviewed on Mar 9, 2021

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Palms Resort at Sugarloaf - Grey House
WATERFRONT fresh & cozy 2 bedroom 35 sea wall<br>New UV light air purification safe
Situated in Cudjoe Key, this vacation home is within 9 mi (15 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Lower Sugarloaf Sound. National Key Deer ...
4.8/5Exceptional! (79 reviews)
Wonderful place
"Had everything we needed! Great stay and can't wait to come back. The bed in the master is one of the most comfortable beds I've ever slept in. A/C kept the house cool and the bait freezer was awesome to have. Fun fishing right out back and being able to pull it from the water and slap it on the ..."

Reviewed on Sep 17, 2021

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WATERFRONT fresh & cozy 2 bedroom 35 sea wall<br>New UV light air purification safe
Key Haven Estates' "Sophisticated Sunsets"; 4br, 4 bath 2,840 sq ft
Situated in Key West, this vacation home is 1.3 mi (2.1 km) from Lower Keys Medical Center and 1.5 mi (2.4 km) from Key West Harbour. Saddlebunch Keys and Key ...
5/5Exceptional! (7 reviews)
"Beautiful home, minutes from Key West! Would come back again"

Reviewed on Jul 12, 2021

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Key Haven Estates' "Sophisticated Sunsets"; 4br, 4 bath 2,840 sq ft
Summerland Breeze - A Resort Style Three House Retreat
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 ...
5/5Exceptional! (1 review)
Sweet Summer Time
"We had THE BEST experience staying at Emily and Randy’s place from beginning to end! They are great people to work with and communicate very well pre-arrival and during the stay. We live in SW Florida and take our summers down to the Keys for the last 8 years. We rent a home 6-8 weeks while there ..."

Reviewed on Aug 12, 2021

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Summerland Breeze - A Resort Style Three House Retreat
Key Haven Estates' "Modern Keys"; 4br/4.5ba - 2,331 interior sq ft
Situated in Key West, this vacation home is 0.7 mi (1.1 km) from Key West Golf Club and 1.8 mi (2.9 km) from Key West Harbour. Lower Keys Medical Center and ...
4.8/5Exceptional! (5 reviews)
Talk about AMAZING
"This property was beyond amazing! It was a great location that was no more than 15mins from anywhere we visited on the island. The house was simply beautiful and clean. There was 8 ladies and having extra bathrooms was perfect for us! We will definitely be back next year. This house is 100% recommended ..."

Reviewed on Jul 7, 2021

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Key Haven Estates' "Modern Keys"; 4br/4.5ba - 2,331 interior sq ft
Casa Calypso- Beautiful Tropical Style House 3 KING Beds POOL 2 mi to beach
This family-friendly Key West vacation home is located by the sea, within 1 mi (2 km) of Lower Keys Medical Center and Key West Harbour. Key West Golf Club and ...
4.9/5Exceptional! (93 reviews)
Great house
"Judy was excellent with communication and the house is adorable! Fully stalked with all the amenities. Very easy to check in and out. Great location just 15 minutes from Duval street and all the action. The beds were very comfortable."

Reviewed on Sep 17, 2021

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Casa Calypso- Beautiful Tropical Style House 3 KING Beds POOL 2 mi to beach
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See all available properties in Summerland Key
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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.

Other property types 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 Sep 27 to Sep 27
4.8/5Exceptional! (34 reviews)
Great location
"This is a nice stand alone property that sits half way between Key West and Marathon Key. A short 30 minute drive will put you in either location."

Reviewed on Aug 11, 2021

Kelly's Kabin private cottage on Summerland Key
Summerland Breeze - A Resort Style Three House Retreat

Summerland Breeze - A Resort Style Three House Retreat

Summerland Key, FL
5/5Exceptional! (1 review)
Sweet Summer Time
"We had THE BEST experience staying at Emily and Randy’s place from beginning to end! They are great people to work with and communicate very well pre-arrival and during the stay. We live in SW Florida and take our summers down to the Keys for the last 8 years. We rent a home 6-8 weeks while there ..."

Reviewed on Aug 12, 2021

Summerland Breeze - A Resort Style Three House Retreat
Charming and Private

Charming and Private

Summerland Key, FL
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
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.

Booking Tips to Find the Best Summerland Key Vacation Homes


How much does it cost to rent a vacation home in Summerland Key?

You can find incredible Summerland Key vacation homes for all types of budgets: between $250 and $299 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Summerland Key?

If you are looking for a great deal on your vacation home in Summerland Key, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Summerland Key?

There are 200 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Summerland Key?

Begin by entering your trip dates to see what type of Summerland Key rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Summerland Key?

Booking Summerland Key vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Summerland Key rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Summerland Key along with your vacation property, into a Summerland Key vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.