Summerland Key Trips (flight + hotel)

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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
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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

Top hotels in Summerland Key

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 P6,372 per night from Aug 31 to Sep 1
P6,372
P9,031 total
Aug 31 - Sep 1
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"This is a beautiful place, a hidden treasure. The breakfast was plentiful with fresh breads, fresh fruit, a variety of cereals, and good hot coffee. The staff was very friendly, helpful, and accommodating. If you have limited mobility, pay attention when you book to make sure you can access the room ..."

Reviewed on Aug 10, 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 P5,652 per night from Aug 17 to Aug 18
P5,652
P6,359 total
Aug 17 - Aug 18
includes taxes & fees
8/10 Very Good! (999 reviews)
"It was great"

Reviewed on Jul 27, 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! (420 reviews)
"This was my first time staying at this property. I can only say that it will not be the last. The staff and the property was such an amazing experience. It is family friendly, close proximity to Key West and very quiet and clean. It was such a pleasure to stay there."

Reviewed on Aug 3, 2025

Get rates
Sugarloaf Key Hotel at KOA Resort
See all 611 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.

What to do in Summerland Key

A fun-filled adventure for the whole family

Guided Clear Kayak Eco-Tour Near Key West

P4,595
per adult
Guided Clear Kayak Eco-Tour Near Key West
Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

P38,795
per traveler
Marathon Backcountry Fishing Charter
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

P1,596
per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
See all activities in Summerland Key

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.