Summerland Key Holidays
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Our guide on 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
Cutthroat Harbor Estates
While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Out Keys and Venture Key.
Sugarloaf Shores
Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Upper Sugarloaf Sound.
Cudjoe Gardens
While Cudjoe Gardens may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Upper Sugarloaf Key and Florida Keys Beaches.
Breezeswept Beach Estates
While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Cook Island and Venture Out Keys.
Summerland Key Holiday
Our pick of the best Summerland Key Hotel Deals
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
NZ$259
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"The staff at Parmer’s is excellent from the check-in person to everyone that works on the grounds. However, this place had to grow on me because my initial reaction was one of disappointment. I think the pictures look much better than what’s actually there. The beach that’s advertised and looks like ..."
Reviewed on 29 Aug 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 28 Aug 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.
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 snorkelling and marine life observation. Bring supplies and reef-safe sun cream 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 holiday 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
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
NZ$96
per adult
88% of travellers recommend
Key West Mangrove Kayak Eco Tour
NZ$138
per adult
100% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
NZ$67
per adult
88% of travellers recommend
Frequently asked questions
How much does a Summerland Key holiday package cost?
You'll find cheap prices 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 holiday to Summerland Key costs.
What are the cheapest months to go to Summerland Key?
If you're hoping to score a cheap Summerland Key holiday package, consider travelling in September, October and November. You'll typically find lower rates on accommodation and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Summerland Key?
Generally, a handful of days is enough to tick off the major attractions during your Summerland Key holiday. However, if you'd like to have some time to relax or go on day trips, think about extending your trip.
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 holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking stays and flights separately. Better still, you can customise 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 holiday package to Summerland Key?
If you've got your Summerland Key holiday 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?
- Choose when to go: Check your calendar and pack your bags. Your favourite season and the activities available will also help you decide when to holiday in Summerland Key.
- Set a budget: Factor in costs such as transportation, flights and meals when calculating how much to save for your trip to Summerland Key. Then, choose a hotel that suits your budget, whether that's an economical stay or a swankier getaway.
- Decide how long to go away for: Now that you're more familiar with Summerland Key, you can figure out the ideal length of your holiday. Put together a draft plan and allocate enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customised Summerland Key holiday package.
Explore a world of travel with Expedia
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- Sugarloaf Shores Hotels
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- Hotels near Key West Visitors Center
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- Summerland Key Hotels
- Smathers Beach
- Southernmost Point
- Fort East Martello Museum and Gallery
- Key West Cemetery
- Clarence S. Higgs Memorial Beach Park
- Mel Fisher Maritime Museum
- Boca Chica Nude Beach
- Big Pine Key Holidays
- Coco Plum Beach
- Mallory Square
- Pigeon Key
- Fort Zachary Taylor Historic State Park
- Key West Holidays
- Key West Butterfly and Nature Conservatory
- Florida Keys Beaches
- Duval Street
- Crane Point Museum and Nature Center
- South Beach
- Visit Big Torch Key
- Visit Port Pine Heights
- Visit Eden Pines
- Visit Lower Florida Keys
- Visit Big Pine Key
- Visit Sugarloaf Shores
- Visit Cudjoe Key
- Visit Melody Key
- Visit Ramrod Key
- Orlando Rental Cars in Bahia Honda Key
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- Global Rent a Car Rental Cars in Lower Florida Keys
- United Rental Cars in Lower Florida Keys
- Dollar Rent A Car Rental Cars in Lower Florida Keys
- Discount Car Rentals Rental Cars in Lower Keys
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
