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 SARĀ 444 per night from Aug 11 to Aug 12
SARĀ 444
SARĀ 622 total
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"We happened upon this quaint resort on a weekend to the Keys. What a great spot! It is not on one of the main keys but is close to Key West and other fun locations. The resort had hammocks to relax in, a pool, docks, outdoor activities and a small breakfast (don't plan on filling up on it if you ..."

Reviewed on 13 July 2026

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! (598 reviews)
"Room was very clean. Staff was very nice. Unfortunately when I was there, the pool was under Construction, but everything else was great."

Reviewed on 15 July 2026

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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
9.4/10 Exceptional! (19 reviews)
"The cabins were pretty much new. Beautiful views. Also the cabins are separate from RV area. Cant wait to go back. Lass that 1/2 hour to Key West. Way better price base foe better rooms and amenities."

Reviewed on 14 July 2026

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Sugarloaf Key RV Resort & Cottages
See all 624 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?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Summerland Key costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Summerland Key?
If you're looking to book a cheap Summerland Key vacation package, consider traveling in September, October and November. You'll typically find better rates on hotels and airfares during these months ā€” ideal for a budget-friendly break.
How to find the best Summerland Key package deals?
Use Expedia's filter tool to find some terrific Summerland Key package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Summerland Key package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Summerland Key vacation as a package?
You can enjoy significant savings on your Summerland Key retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Summerland Key?
If you're considering an impromptu Summerland Key getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Summerland Key?

  1. Pick your dates: The things you plan to do in Summerland Key and your preferred season can help you decide when to get away.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will likely be the largest expense during your trip to Summerland Key.
  3. Decide how long to go for: Now that you know more about Summerland Key, you can work out the perfect length of your vacation. Create a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Summerland Key vacation package that brings all your bookings together.