Summerland Key Vacations

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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
A calm lake with several white birds, including herons and pelicans, on the water's edge.

Cutthroat Harbor Estates

While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby.

Find hotels in Cutthroat Harbor Estates

Find the Best Summerland Key Vacation Packages

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 NT$4,563 per night from Jul 6 to Jul 7
NT$4,563
NT$6,174 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Very nice staff"

Reviewed on 2026/6/26

Parmer's Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (592 reviews)
"Very well maintained and clean. Pool area is very nice and margaritas from the bar are great."

Reviewed on 2026/6/30

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Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

3 out of 5
311 Johnson Rd Summerland Key FL
9.2/10 Wonderful! (15 reviews)
"The experience was a good one from dealing with Elizabeth a great host to the property was in great shape.The snack stand and entertainment was not supplied but we were in off season but everything was good."

Reviewed on 2026/6/30

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Sugarloaf Key RV Resort & Cottages
See all 629 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.

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.
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Frequently asked questions

How much does a Summerland Key vacation 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 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?

  1. 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.
  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 vacation. 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 customized Summerland Key vacation package.

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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.