Summerland Key Vacation Rentals

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    Upfront pricing

    We're not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Rentals in Summerland Key

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

9.6 out of 10, Exceptional, (78)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water
Springs Venture Out Dolphin House (#386) with beautiful open water views
Outdoor pool, a heated pool

Springs Venture Out Dolphin House (#386) with beautiful open water views

9.2 out of 10, Wonderful, (100)
"We absolutely loved our time here! GORGEOUS view of the bay! It was exactly what we needed for our guys trip!"
Springs Venture Out Dolphin House (#386) with beautiful open water views
Charming cottages, dockage, pool, just minutes to Key West
Fridge, microwave, oven, stovetop

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (119)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
Charming cottages, dockage, pool, just minutes to Key West
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (190)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (86)
"I will sum it up by saying it was ok. It was a place to stay, would I book it again? No"
Canal front, dockage, 2 bedroom, 2 bath
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
A heated pool

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

9.8 out of 10, Exceptional, (8)
"Beautiful place!"
$740 nightly
The price is $820
Sep 1 - Sep 2
Total with taxes and fees
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
On the beach, beach towels

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (237)
"Clean and inviting property, great location, attentive host. Highly recommend."
$737 nightly
The price is $818
Sep 1 - Sep 2
Total with taxes and fees
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (145)
"We had a nice stay at the cottages. Location worked well for our fishing excursions and access across the street to old RT 1 to walk the dogs. "
Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Outdoor dining

Cudjoe Cottages, swimming pool, just 20 miles from Key West

8.8 out of 10, Excellent, (145)
"Near to Key West in a quiet neighborhood. "
Cudjoe Cottages, swimming pool, just 20 miles from Key West
A Tropical Luxury Getaway, Your own private resort!!
Outdoor pool, a heated pool

A Tropical Luxury Getaway, Your own private resort!!

10.0 out of 10, Exceptional, (38)
"The house and pool were very nice."
A Tropical Luxury Getaway, Your own private resort!!
Waterfront Home
Terrace/patio

Waterfront Home

8.8 out of 10, Excellent, (169)
"Great price great location "
Waterfront Home
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (85)
"My husband and I stayed with our son in the cottage and it was everything we needed. Great location, beautiful pool on the water, and just enough space. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (152)
"The place was spacious, very clean and beautiful!"
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Pool

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

10.0 out of 10, Exceptional, (3)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Cottage with swimming pool and dockage, just minutes to Key West!
Miscellaneous

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (154)
"The cottage was comfortable, and the bed was just right. We were in the Keys for a funeral, so not much running around."
Cottage with swimming pool and dockage, just minutes to Key West!
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Beach nearby, sun loungers, beach towels

Mini lobster available! Open Water View from porch , dock, bikes, kayaks

9.8 out of 10, Exceptional, (122)
"We loved having our own space for a boat. Great location."
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Cottage with Pool and Dockage, just minutes to Key West
Pool

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (152)
"Good Fishing, Good local eateries. "
Cottage with Pool and Dockage, just minutes to Key West
Sea La Vie #197 - Oceanfront, Big Boats Welcome Here!
A heated pool

Sea La Vie #197 - Oceanfront, Big Boats Welcome Here!

2.5 star property
10.0 out of 10, Exceptional, (6)
"Our stay was wonderful! The view is amazing, the home was clean and very well stocked. We had a wonderful time."
Sea La Vie #197 - Oceanfront, Big Boats Welcome Here!
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Marina

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

10.0 out of 10, Exceptional, (227)
"We like staying on the lower keys and this nest, clean, perfectly appointed condo was perfect! And the owners were lovely and easy to communicate with. A restful and memorable vacay!"
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Outdoor dining

**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool

9.6 out of 10, Exceptional, (39)
"This was our second time staying here, and it was amazing both times! We love the view as well as the pool and beach area. Our host was extremely helpful and acessible to us!! We will be looking to book again in our next trip to the Keys! "
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
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.
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Top Summerland Key Hotel Reviews

Find out more about Summerland Key

Find out more about Summerland Key

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 low season months. For more hustle and bustle, you may prefer to visit Summerland Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $818 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Old Florida Style, wrap around porch, boat basin for dockage, open water: This Summerland Key vacation home rental is located by the ocean and offers a garden, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family. Some other top choices in Summerland Key are Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West and Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!.

How many vacation rentals are there in Summerland Key?

Choose from 483 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.