Summerland Key Holidays

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Your Summerland Key Holiday

Say bye-bye to planning worries and hello to a Summerland Key holiday package. With everything organised before you go, you can focus on discovering this city, starting with Breezeswept Beach Estates, which is good for adventure sports, fishing and watersports. Like to explore your new surroundings? Big Pine Key Flea Market, Cook Island and Blue Hole are some of the top places to visit during a trip to Summerland Key. That dream Summerland Key holiday is only clicks away. Browse accommodation, flights and more on Expedia for a trip that's tailored just for you.

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
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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 Upper Sugarloaf Key.

Find hotels in Cutthroat Harbor Estates

Summerland Key Holiday

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

Our pick of the best Summerland Key Hotel Deals

Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$260 per night from 26 Aug to 27 Aug
AU$260
26 Aug - 27 Aug
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Loved the property and all of the free activities! We definitely took advantage of the kayaks, paddle boards, pool and hammocks."

Reviewed on 30 Jul. 2025

Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 10 Aug to 11 Aug
AU$172
10 Aug - 11 Aug
includes taxes & fees
8/10 Very Good! (998 reviews)
"It was great"

Reviewed on 27 Jul. 2025

Sugar Loaf Lodge
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939, Summerland Key, FL
9.6/10 Exceptional! (419 reviews)
"We stayed for July 4th and it was perfect! Loved the suite and as a family it was very convenient to have a kitchen, washer and dryer!"

Reviewed on 29 Jul. 2025

Get rates
Sugarloaf Key Hotel at KOA Resort
See all 596 properties in Summerland Key
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.
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Beach Holidays
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What to do in Summerland Key

Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

AU$85
per adult
86% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Parasailing Downtown

Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides

AU$97
per traveller
90% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

AU$69
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Summerland Key

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.