Summerland Key Holidays
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Top Flight + Hotel Deals in Summerland Key
Price found within the past 48 hours. Click for updated prices.
Pelican Hotel
South Beach
€1,255
per person
5 Nov - 12 Nov
found 22 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
9.2/10 Wonderful! (499 reviews)
Location is fantastic, as it the restaurant. Staff was great. The room was very small, and the bed felt like concrete.
Reviewed on 1 Sept 2026
Eden Roc Miami Beach
Mid Beach
€1,626
per person
5 Nov - 12 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.6/10 Excellent! (3,530 reviews)
The room was a nice room that over looked the water the shower and bath was amazing and the bed was super comfortable. When first checked in the guy behind the desk didn’t give us any direction to our room in which we had to ask him! Although our room was ready very early which was good. Pool and beach was nice and we like it because it was close to south beach by bus!! Overall good experience and stay if you don’t like to be on south beach
Reviewed on 1 Sept 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 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 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 Venture Out Keys.
Top hotels in Summerland Key
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
€144
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Hotel acogedor y especial."
Reviewed on 31 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.
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.
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.
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.
Squirrel Key
Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.
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.
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
€48
per adult
88% of travellers recommend
Key West Mangrove Kayak Eco Tour
€69
per adult
100% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
€42
per adult
82% of travellers recommend
Frequently asked questions
How much does a Summerland Key holiday package cost?
You'll find cheap prices from €941 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
