The Best Summerland Key, FL Resorts from $170

A coastal road with a beach on one side and a marina with boats on the other.

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Our top choices for Summerland Key resorts

A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.

1. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Craige

$151 nightly

Sep 29 - Sep 30

Total with taxes and fees

A marina with boats docked, a lighthouse, and a resort with outdoor seating.

2. Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Marathon

Rick

$180 nightly

Oct 11 - Oct 12

Total with taxes and fees

A pool area with lounge chairs and a cabana.

3. Ocean Key Resort - A Noble House Resort

Key West Historic District

Brian

$263 nightly

Sep 29 - Sep 30

Total with taxes and fees

A wooden deck with wicker furniture and a glass balustrade overlooking a beach.

4. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Coni

$198 nightly

Sep 30 - Oct 1

Total with taxes and fees

A hotel with a swimming pool, balconies, and a view of the sea.

5. Hyatt Centric Key West Resort and Spa

Key West Historic District

yendy

$264 nightly

Sep 28 - Sep 29

Total with taxes and fees

A beach with a wooden pier, palm trees, and beach umbrellas.

6. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

$259 nightly

Oct 4 - Oct 5

Total with taxes and fees

A beachfront hotel with a covered patio, palm trees, and a boat on the sand.

7. Pier House Resort & Spa

Key West Historic District

Cheryl

$291 nightly

Oct 4 - Oct 5

Total with taxes and fees

A pool area with lounge chairs and palm trees.

8. Santa Maria Suites

Old Town Key West

Anthony

$309 nightly

Sep 27 - Sep 28

Total with taxes and fees

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Top Summerland Key Hotel Reviews

Sugar Loaf Lodge

10/10 Excellent

"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"

Waterfront 2BR, Dock,Golf Cart, trailer parking,Open Water Views Venture Out 320

10/10 Excellent

"Our three-night stay at this exceptional waterfront retreat was nothing short of extraordinary. Set against sweeping open-water views, the property offers that rare combination of effortless comfort, understated elegance, and a truly idyllic setting.From the moment we arrived, the home felt like a private escape designed for relaxation. The interiors were inviting and beautifully maintained, while the waterfront setting provided a spectacular backdrop throughout our stay. Mornings overlooking the water and quiet evenings by the dock were among the many memorable moments.The private dock and golf cart elevated the experience even further, making it wonderfully easy to explore the community and enjoy everything the resort has to offer. Every detail seemed to encourage slowing down, savoring the surroundings, and simply enjoying being there.Although we stayed only three nights, the experience felt wonderfully restorative—and we found ourselves wishing we had booked a much longer stay. This is the kind of place where the pace immediately changes, the views become part of the experience, and a short getaway feels like a true escape.Beautifully situated, exceptionally comfortable, and surrounded by breathtaking waterfront scenery, this home is a destination in itself. We would return without hesitation and look forward to our next visit. A truly memorable stay in a spectacular setting. Host Mel is wonderful and very attentive."

Ocean Breeze House - Summer fun Sleeps 8 boating, fishing and 🦞 Lobster season.

10/10 Excellent

"Glen was more than helpful with our visit. He was very prompt and knowledgeable with the area. The property is very large and tranquil. The house was very spacious and accommodating. We would recommend this property!!"

Direct Oceanfront Cottage-Sunrise View- #2,

10/10 Excellent

"Delightful cottage. It can get a little warm without central AC but the window units do a pretty good job of cooling it down. The kitchen doesn’t have a unit and had I actually wanted to cook I imagine it might be too hot. But if you’re not planning to cook and just need a nice comfortable space for o relax after a full day on and in the water this is it! We will definitely be looking to come back next year."

A Tropical Luxury Getaway, Your own private resort!!

10/10 Excellent

"This property is fantastic! It’s in perfect condition, both inside and out. The grounds were immaculate. They had everything you could need, from pool games and beach games to beach towels, life jackets, entertainment around the pool, large porches, a dock for a boat, a fish cleaning area at the dock’s end, paddle boards, kayaks, and more. The layout was ideal for a large group with multiple families. The host was super responsive and helpful with all our questions. We can tell they really care about the home and the property. Definitely recommend! We cannot wait to come back"

Find out more about Summerland Key

Summerland Key Resorts information

Number of reviews	4,377
Accommodation	2 Resorts
Lowest Price	$170
Highest Price	$1,491

Frequently asked questions

What can I expect from a resort vacation in Summerland Key?

You deserve some time off, and a resort is just the place to treat yourself to the amenities and services you need for a relaxing stay in Summerland Key. One of the comfortable resorts in the surrounding area might be just what you're looking for, whether you want great restaurants on site, a state-of-the-art fitness center, or fun activities to try.

What's a top resort in Summerland Key?

Our highest-rated resorts around Summerland Key: Luxury Pull Thru Rv lot with access to all the Resorts amenities! - Family-friendly resort. 1.9 mi (3 km) from Summerland Key. Has a garden, an outdoor pool, and a hot tub. ISLAND PARADISE - Family-friendly resort. 1.8 mi (2.9 km) from Summerland Key. Enjoy the garden, outdoor pool, and hot tub. Pier House Resort & Spa - Beach resort steps from Mallory Square. 23.8 mi (38.2 km) from Summerland Key. Amenities include a private beach, 2 bars, and a full-service spa. Guests love the pool. Casa Marina Key West, Curio Collection by Hilton - Beach resort, 5-minute walk from Florida Keys Beaches. 23.1 mi (37.1 km) from Summerland Key. Access to 2 outdoor pools, a private beach, and a full-service spa.

How many hotel resorts will I find in Summerland Key?

Choose among Expedia's 5 resorts in Summerland Key where you'll find top-notch bars, beautiful guest rooms, and more.

What can I do in Summerland Key?

For some time by the water, you can head to Florida Keys Beaches and Sugarloaf Beach. Additional attractions in the area include Upper Sugarloaf Key and Venture Out Keys.

What's the weather like in Summerland Key?

The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. Average annual precipitation for Summerland Key is 35 inches.

What's the best way to get to and around Summerland Key?

Fly into Key West Intl. Airport (EYW), which is located 20.9 mi (33.6 km) from the city center. Otherwise, you can search for flights to Marathon, FL (MTH-Florida Keys Marathon), which is 25.1 mi (40.3 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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Things to do in Summerland Key

Room 1

Check prices for these dates

Our top choices for Summerland Key resorts

1. DoubleTree Resort by Hilton Grand Key - Key West

2. Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

3. Ocean Key Resort - A Noble House Resort