Summerland Key Holidays from NZ$2,741
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The Latest Summerland Key Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive
Old Town Key West
NZ$2,886
per person
24 Dec - 27 Dec
found 15 hours ago
Return direct flight included
Charlottesville (CHO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Great stay. Older locations like this face many challenges so there is certainly more work to be done but everything worked like new and the staff was super helpful even offering an upgrade at no charge due to availability.
Reviewed on 11 Oct 2026
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 Key and Venture Out Keys.
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 Sugarloaf Beach.
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 Big Pine Key Flea Market.
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$352
3 Nov - 4 Nov
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Great place for the family."
Reviewed on 13 Oct 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (647 reviews)
"KOA PROPERTY"
Reviewed on 12 Oct 2026
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
NZ$223
15 Oct - 16 Oct
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"We like the fact that we didn’t have to go far after the wedding. The staff were great. The atmosphere was good. The rooms were not what we expected for the price. The bathroom floor was dirty and the door was warped and you had to really push on it to close. The tv kept booting us out. The beds ..."
Reviewed on 14 Oct 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.
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.
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.
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.
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.
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?
Squirrel Key
Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.
What to do in Summerland Key
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
NZ$57
per adult
82% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
NZ$97
per adult
88% of travellers recommend
Key West Mangrove Kayak Eco Tour
NZ$140
per adult
100% of travellers recommend
Frequently asked questions
How much does a Summerland Key holiday package cost?
You'll find cheap prices from NZ$2,741 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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- 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
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- Coco Plum Beach
- Mallory Square
- Pigeon Key
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- Key West Butterfly and Nature Conservatory
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- Duval Street
- Crane Point Museum and Nature Center
- South Beach
- Visit Big Torch Key
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- Visit Sugarloaf Shores
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- Visit Melody Key
- Visit Ramrod Key
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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.
