Summerland Key Holidays

Book a Hotel + Flight or Car together to unlock savings

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

Top hotels in Summerland Key

Parmer's Resort
Parmer's Resort
2.5 out of 5
565 Barry Avenue, Summerland Key, FL
The price is 3.094.939 ₫ per night from 25 Jun to 26 Jun
3.094.939 ₫
4.336.550 ₫ total
25 Jun - 26 Jun
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"A Gem of a Property! If you have ever wondered what the Florida Keys were like before the mega corporations took over, this is it. Charming, with so many personal touches that it instantly feels like home. Location is fantastic, quiet with great amenities, and only a beautiful, easy drive to Key ..."

Reviewed on 13 Jun 2025

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
9.6/10 Exceptional! (393 reviews)
Great time
"Amazing spot..family friendly…great hotel and amenities…"

Reviewed on 21 Jun 2025

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Sugarloaf Key Hotel at KOA Resort
Looe Key Reef Resort
Looe Key Reef Resort
2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
7.4/10 Good! (1,002 reviews)
"Very cute hotel. The rooms are recently renovated."

Reviewed on 12 Jun 2025

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Looe Key Reef Resort
See all 600 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.

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.