Summerland Key Vacations from $480

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Your Summerland Key Vacation

The hassle-free way to experience this interesting city is with a tailor-made Summerland Key vacation package. Base yourself in the neighborhood of Sugarloaf Shores, which is great for families, fishing and views or go someplace else — our package deals are all about you. Cook Island, Big Pine Key Flea Market and Blue Hole are just some of the sights you'll want to see during your trip to Summerland Key. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Summerland Key vacation plans in motion!

The Latest Summerland Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Luxuri Suites

Luxuri Suites

South Beach
$480
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
6.8/10 (57 reviews)
Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work.

Reviewed on Jul 9, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$1,495
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Great location and nice historic home

Reviewed on Aug 1, 2026

Casablanca Miami Beach

Casablanca Miami Beach

North Beach
$2,821
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
5.8/10 (327 reviews)
Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No beach chair, no wagon and the umbrella covered 1 person. I reached out to the person but never showed up with clean sheets. I had to invest in my stay detergent, sanitizing wipes, trash bags and toilet covers. Let me know forget to say, on my first stay the bottom of my feet was all black from the floors being super dirty. The only good thing of the place was the beach distance.

Reviewed on Jul 23, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
$6,765
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

The Marlin Hotel

The Marlin Hotel

South Beach
Save 100% on your flight
$509
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,005 reviews)
The location was great, the bar convenient, the restaurant downstairs was great. Overnight parking was reasonable.

Reviewed on Aug 2, 2026

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Where to stay in Summerland Key

Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. Learn more about Summerland Key
A calm lake with several white birds, including herons and pelicans, on the water's edge.

Cutthroat Harbor Estates

While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby.

A waterfront property with a pool, palm trees, and a building with a white roof.

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

Boat traveling under the Seven Mile Bridge, Florida Keys, USA

Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.

An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Big Pine Key Flea Market and Venture Out Keys are some notable places to visit nearby.

Stay near popular Summerland Key attractions

Sugarloaf Beach

8.4/10 (38 reviews)
This secluded private beach on Sugarloaf Key offers a tranquil escape from the busier Florida Keys shorelines. Guests enjoy pristine views and peaceful sunbathing in a natural, amenity-light setting.
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Upper Sugarloaf Key

8.6/10 (54 reviews)
Upper Sugarloaf Key serves as a gateway to the Great White Heron National Wildlife Refuge with pristine waters. Kayak through mangroves at dawn to spot diverse bird species in this tranquil Florida Keys ecosystem.
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Upper Sugarloaf Sound

9.2/10 (17 reviews)
Glide through Upper Sugarloaf Sound's tranquil waters surrounded by vibrant mangroves and diverse birdlife. Kayak or paddleboard this peaceful Florida Keys retreat to experience nature at its most serene.
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Pye Key

This unspoiled island near Summerland Key offers pristine waters for snorkeling and marine life observation. Bring supplies and reef-safe sunscreen for your half-day adventure in this natural Florida Keys sanctuary.
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Venture Key

This private Florida Keys community offers waterfront vacation rentals with direct access to pristine boating waters. Enjoy the heated pool and tennis courts before setting out from the marina for a day of fishing.
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Crab Key

Crab Key is a private residential island off Summerland Key in the Florida Keys with no public access. This exclusive enclave remains one of the few truly private islands in the Keys.
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Squirrel Key

Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.
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Boondocks Grille & Draft House

Boondocks Grille & Draft House is just one of the places to see in Summerland Key, so why not enjoy the other things to explore during your travels?
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What to do in Summerland Key

Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$45
per adult
88% of travellers recommend
Key West Conch Tour Train
Key West's Island Eco Tour: Kayaking, Snorkeling & Sandbar Adventure

Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour

$145
per adult
98% of travellers recommend
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
Key West Clear Kayak Eco Tour

Key West Clear Kayak Eco Tour

$60
per adult
Key West Clear Kayak Eco Tour
See all activities in Summerland Key

Summerland Key Hotel Deals

Parmer's Resort

Parmer's Resort

565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
$129 nightly
$145 total
Aug 19 - Aug 20
Total with taxes and fees
9/10 Wonderful! (1,009 reviews)
"Room was small but we booked last minute for lobster season but everything else was great!!"

Reviewed on Aug 6, 2026

Parmer's Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (611 reviews)
"Overall it was a great experience. All staff is really kind. Our room had dogs hair on the floor when I first swept and bed isn’t too comfortable but room overall looks beautiful and is well maintained. Bar and pool close a bit early but like everything else in the keys. Only annoying thing is marina ..."

Reviewed on Jul 29, 2026

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Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

311 Johnson Rd Summerland Key FL
Sugarloaf Key RV Resort & Cottages
See all 625 properties in Summerland Key
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.

Find the Best Summerland Key Vacation Packages

Summerland Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Max Temp Winter
75ºF
Max Temp Summer
85ºF
Top Sights
Bahia Honda State Park, Florida Keys Beaches and Calusa Beach

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Frequently asked questions

How much does a Summerland Key vacation package cost?
You'll find cheap prices from $480 on Expedia for your Summerland Key break. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Summerland Key costs.
What are the cheapest months to go to Summerland Key?
August, September and October are the best times to search for cheap Summerland Key vacation packages. Opting to travel in quieter months means you'll typically find lower prices on flights and hotels.
How many days is enough for Summerland Key?
With a well-planned schedule, you can easily hit the most popular Summerland Key sights in a few days. But if you'd like to discover lesser-known spots or go on day tours, consider booking your Summerland Key vacation for longer.
How to find the best Summerland Key package deals?
Begin your search for a Summerland Key package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Summerland Key package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Summerland Key escape off to a flying start.
Is it cheaper to book a Summerland Key vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking stays and flights separately. Better still, you can customize your Summerland Key escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Summerland Key?
If you've got your Summerland Key vacation dates confirmed, book as soon as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Summerland Key?
  1. Pick your dates: The things you plan to do in Summerland Key and your preferred season can help you decide when to travel.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and airfares. Your hotel will likely be the largest expense during your trip to Summerland Key.
  3. Use Expedia's trip planning tool to explore Summerland Key: Research every part of your trip to Summerland Key with this comprehensive planner. Invite your family and friends to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how many days away: Start by listing all the sights and activities you want to experience in Summerland Key. Then, estimate how long you'll need for each, along with any travel time.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalized Summerland Key vacation package.
  6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip in nature, you won't have to worry about missing out on Summerland Key's best offerings. Find all the fun things to do in Summerland Key with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Summerland Key vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Summerland Key trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.