Summerland Key Vacations from $565
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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.
Lexington by Hotel RL Miami Beach
Mid Beach
$719
per person
Nov 7 - Nov 14
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.4/10 Good! (1,328 reviews)
Just finished our 5 night visit, overall this hotel is fine. Before travelling I read a lot of reviews regarding ongoing maintenance work which I hadn't realised when booking so this made me anxious. There clearly is alot of work that still needs to be done here but it was cheap and comfortable for the time we were there. We did have an issue with the room door not closing but this was sorted asap. The water did take a while to warm up but once it did it was boiling. The location of this hotel was just perfect for us, the beach being right outside was everything we wanted and I miss it already. If you're not going to be in the hotel too much and on a budget then this is fine please ignore the bad reviews. I really hope the renovations bring this hotel back to life purely for the location. Staff were all really friendly and welcoming
Reviewed on Aug 31, 2026
The Local House
South Beach
$1,049
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
Great location on Ocean Drive, few mins walk to the main restaurants/bars. Rooftop pool was lovely after a day at the beach. Great to have sunbeds/towels provided for the beach which is a 5 minute walk across the road.
Room was really nice with coffee machine and great view from the balcony.
Check in was easy, 100$ security deposit for each night n weed to be paid which I don’t know about. Would 10000% stay again.
Reviewed on Aug 29, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$7,442
per person
Oct 9 - Oct 12
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
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See all available trips from Columbus to Summerland Key
View all tripsWhere to stay in Summerland Key
Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. Learn more about Summerland Key
Cutthroat Harbor Estates
While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Venture Key are some notable places to visit nearby.
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.
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.
Breezeswept Beach Estates
While Breezeswept Beach Estates isn't home to many top sights, Cook Island 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.
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.
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.
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.
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.
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.
Squirrel Key
Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.
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?
What to do in Summerland Key
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
$130
per adult
98% of travellers recommend
Summerland Key Hotel Deals
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
$158 nightly
$178 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,005 reviews)
"Hotel acogedor y especial."
Reviewed on Aug 31, 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9.4/10 Exceptional! (29 reviews)
"It was close to Key West and the price was fair. The room was clean. Although I would put blinds on the windows, it's too bright in the morning for sleeping in. And although it showed the tiki bar area open at 4pm. It wasn't opened either night we were there which was very disappointing."
Reviewed on Aug 28, 2026
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 $565 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?
- Pick your dates: The things you plan to do in Summerland Key and your preferred season can help you decide when to travel.
- 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.
- 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.
- 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.
- 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.
- 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.