Summerland Key Vacations from ￥209,096
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The Latest Summerland Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
President Hotel Villa
South Beach
￥209,096
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Buen lugar excelente ubicación cerca de todo
El único detalle es que las instalaciones son un poco antiguas, adicional no nos hicieron limpieza un dia en la habitación
Reviewed on Oct 11, 2026
Boulan South Beach
South Beach
￥273,132
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (1,017 reviews)
The room was like an apartment with plenty of space. Floor needed washing. Kitchen amenities were lacking in all areas for cooking and cleaning. Bathrooms and shower were very good. Technical issues with TV. Patio was very large but dirty. People throw their cigarette butts down on us. Loved the area and proximity to the beach. Roof pool and bar were excellent. Great bartender. Wife and I were there for 7 days. Price was reasonable. We would return again.
Reviewed on Oct 14, 2026
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 Cutthroat Harbor Estates isn't home to many top sights, Venture Key and Venture Out Keys 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 Big Pine Key Flea Market are some notable places to visit nearby.
Find the Best Summerland Key Vacation Packages
Summerland Key Hotel Deals
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
￥23,215
￥31,284 total
Nov 3 - Nov 4
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Great place for the family."
Reviewed on Oct 13, 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (648 reviews)
"I cannot say enough good things about this property. The staff is incredibly friendly and helpful. The amenities are great and the hotel itself is very clean and fairly modern. We had three teenagers with us and we had a blast every day. We had bad weather, but there were still so many things to ..."
Reviewed on Oct 14, 2026
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
￥22,206
￥24,982 total
Oct 26 - Oct 27
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 Oct 14, 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 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.
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.
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
Key West Sunset Cruise & Glass Bottom Eco Tour
￥10,974
per adult
76% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
￥8,723
per adult
88% of travellers recommend
Frequently asked questions
How much does a Summerland Key vacation package cost?
You'll find cheap prices from ￥209,096 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?
If you're hoping to score a cheap Summerland Key vacation package, consider traveling in September, October and November. You'll typically find lower rates on accommodations 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 vacation. 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 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?
- Choose when to go: Check your calendar and pack your bags. Your favorite season and the activities available will also help you decide when to vacation 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 vacation. 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 customized Summerland Key vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
