Summerland Key Holidays from £687
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Your Summerland Key Holiday
The hassle-free way to experience this interesting city is with a tailor-made Summerland Key holiday package. Base yourself in the neighbourhood 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 travelling. Browse the wide range of options on Expedia today and put your Summerland Key holiday plans in motion!
Top Summerland Key Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Private Oasis at Arya
Coconut Grove
£971
per person
17 Nov - 24 Nov
found 10 hours ago
Return direct flight included
London (LHR) to Miami (MIA)
8.6/10 Excellent! (1,034 reviews)
Tv did not work my whole stay. Even after telling me they would be doing rescheduled repairs on it .
Reviewed on 11 Sept 2026
Shore View Hotel
Hollywood Beach
£961
per person
2 Nov - 9 Nov
found 11 hours ago
Return flight included
London (LON) to Miami (MIA)
9.4/10 Exceptional! (49 reviews)
Room was not clean- kitchen sink in particular was filthy. Check in was terrible- no one at the office, stood outside for 45 mins waiting for someone to answer the phone. Would not stay here again.
Reviewed on 27 Apr 2026
President Hotel
South Beach
£720
per person
17 Nov - 24 Nov
found 10 hours ago
Return direct flight included
London (LHR) to Miami (MIA)
8.4/10 Very good! (2,738 reviews)
The staff for super friendly. Wished it had accurate descriptions of the rooms on Expedia before booking.
Reviewed on 11 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 Munson Island.
Summerland Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Max Temp Winter | 24ºC |
Max Temp Summer | 29ºC |
Top Sights | Bahia Honda State Park, Florida Keys Beaches and Calusa Beach |
Top hotels in Summerland Key
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
£122
25 Sept - 26 Sept
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
Reviewed on 11 Sept 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (629 reviews)
"The property was perfectly located to go either direction during our stay. Having the beach and pool was great for our kiddo when we wanted to stay at the property and relax. The staff were all very kind and the room was spotless when we arrived."
Reviewed on 12 Sept 2026
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9.2/10 Wonderful! (31 reviews)
"Make sure to meet Lena and get the right place and deal from her"
Reviewed on 10 Sept 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
£41
per adult
88% of travellers recommend
Key West Mangrove Kayak Eco Tour
£59
per adult
100% of travellers recommend
Frequently asked questions
Why should I book my Summerland Key holiday with Expedia?
Choose Expedia to arrange your next big adventure simply and all in the same place. Our top tip for getting a great deal on a Summerland Key retreat? Bundle your accommodation, flights and/or hire car into a package holiday. Then add a few exciting tours and activities. Most bookings also come with flexible cancellation policies, so there's no need to panic if you have to switch up your travel plans. Round-the-clock help with making tweaks to your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Summerland Key?
If you enjoy the atmosphere of peak season, visit Summerland Key in January, February and March. If you'd like a calmer vibe, August, September and October are better times to visit. With daytime average temperatures of 21ºC, January is the coolest period in Summerland Key. The warmest month is August, when you can expect average temperatures of 29ºC throughout the day. Whatever the weather conditions, you'll discover loads to keep you occupied here.
What is the top hotel for my holiday in Summerland Key?
Create lasting memories in Summerland Key by choosing Isla Bella Beach Resort & Spa as your home base and gateway to adventure and exploration.
How do I get a cheap holiday to Summerland Key?
Find flights that suit your schedule, add a hotel to your booking and see how much you save with a Summerland Key holiday. It's as easy as that! From hotels and flights to activities and hire cars, Expedia is where your cheap holiday begins. And with more than 400 partner airlines and 321,000 properties worldwide to choose from, you won't be short of choice. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Summerland Key holiday?
Offering must-see tourist attractions such as Florida Keys Beaches and Sugarloaf Beach, a holiday in Summerland Key is packed with fun places to visit. National Key Deer Refuge Visitor Centre and Upper Sugarloaf Key are two other sights also worth checking out.
Do I need a visa for my Summerland Key holiday?
Research the latest rules on official government websites. Your nationality and whether you're visiting for study, leisure or business will determine if you require a visa for Summerland Key. Familiarise yourself with the application process, including the required documentation, fees and turnaround times. Submit your application well in advance to allow sufficient time for processing. Some visas may take several weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Summerland Key holiday?
Although everyone's personal style differs, it can be helpful to have some guidelines for what to bring during your holiday in Summerland Key. Think about looking up social media before leaving for inspiration on fashion trends or dress codes. Daytime temperatures in January, Summerland Key's coolest month, average 21ºC. August marks this city's warmest month when average temperatures reach 29ºC. Our advice? Take the guesswork out of what to pack and check the weather forecast.
What does an Expedia Summerland Key holiday include?
With Expedia, you can select a combination of flights, car hires and hotels to build your ideal Summerland Key travel package. Once you've made your booking, simply add on fun stuff like sightseeing tours and activities. Don't forget, the more you bundle, the more cash you'll save! Private holiday homes and cottages are two of the most sought-after property types in Summerland Key. No matter your holiday style or group size, you can rely on Expedia for the freedom to tailor your next big adventure.
Does Expedia offer Book Now, Pay Later Summerland Key holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has come up with a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a fabulous getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Check out these flexible payment options:
- Pay monthly holidays: Klarna offers manageable monthly payment plans that work for all types of budgets, so you can take that well-deserved holiday sooner.
- No-deposit holidays: Clicking on the "book now" button is much easier with this payment plan. With no upfront fee for your escape, you can Book Now, Pay Later and start packing your suitcase.
Can I choose my airline with a Summerland Key Expedia holiday?
Yes — and it's easy too. Expedia has access to more than 400 partner airlines throughout the world. Our packages give you the flexibility to pick from available flights, hotels and activities that suit you.
Explore a world of travel with Expedia
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- Flights to Key West
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- Flights from Manchester (MAN) to Key West (EYW)
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- Flights from Miami (MIA) to Key West (EYW)
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- Visit Bahia Honda Key
- Visit Eden Pines
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- Visit Big Pine Key
- Visit Boca Chica Key
- Calusa Beach
- Clarence S. Higgs Memorial Beach Park
- Visit Cow Key
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- Curry Hammock State Park
- Duval Street
- Ernest Hemingway Home and Museum
- Everglades National Park
- Fort East Martello Museum and Gallery
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- Vaca Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
