Summerland Key Vacations from $494

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Your Summerland Key Vacation

The hassle-free way to experience this interesting city is with a tailor-made Summerland Key vacation package. Base yourself in the neighborhood of Sugarloaf Shores, which is great for families, fishing and views or go someplace else — our package deals are all about you. Cook Island, Big Pine Key Flea Market and Blue Hole are just some of the sights you'll want to see during your trip to Summerland Key. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Summerland Key vacation plans in motion!

The Latest Summerland Key vacation packages

Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was $983, price is now $494 per person
$494
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,414 reviews)
The only thing missing was breakfast. We were given drink vouchers, however we don’t drink.

Reviewed on Aug 21, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $12,817, price is now $5,733 per person
$5,733
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Barnacle Resort

Barnacle Resort

3 out of 5
Long Beach Estates
Price was $2,050, price is now $1,015 per person
$1,015
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (39 reviews)
Perfect place for a quiet getaway.

Reviewed on May 24, 2025

President Villa

President Villa

3.5 out of 5
South Beach
Save 100% on your flight
Price was $1,013, price is now $507 per person
$507
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Hospitable staff, clean, location ideal to walking distance to beach and shopping. Safe place!

Reviewed on Aug 8, 2025

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Price was $1,698, price is now $850 per person
$850
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (294 reviews)
We loved our stay at the Bentley Hotel! The staff was so friendly and always took the initiative to help us out. It was my girlfriend's birthday and when they learned aboit it they brought champagne, snacks to the room and left us a heartfelt card. Thank you again for your hospitality. We cannot wait to be back again!

Reviewed on Aug 24, 2025

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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

Discover the most popular places to visit in Summerland Key

Upper Sugarloaf Sound

Upper Sugarloaf Sound

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.

Upper Sugarloaf Sound

Sugarloaf Beach

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?

Sugarloaf Beach

Upper Sugarloaf Key

Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.

Upper Sugarloaf Key

What to do in Summerland Key

Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

$667
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

$27
per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

$27
per adult
Full Day Trip in Key West from Miami
See all activities in Summerland Key

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
$148 nightly
The price is $167 total per night from Sep 8 to Sep 9
$167 total
Sep 8 - Sep 9
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Great place all around, will be going back in the future!"

Reviewed on Aug 16, 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
$99 nightly
The price is $111 total per night from Sep 1 to Sep 2
$111 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (999 reviews)
"Great sleep"

Reviewed on Aug 20, 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! (427 reviews)
"Staff was very nice and friendly. The resort itself if clean and spacious. There’s a lot of good spots to eat at within a 15 minute drive. The beach was nice and clean"

Reviewed on Aug 14, 2025

Get rates
Sugarloaf Key Hotel at KOA Resort
See all 608 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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Frequently asked questions

How much does a Summerland Key vacation package cost?
You'll find cheap prices from $494 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?
August, September and October are the best times to search for cheap Summerland Key vacation packages. Opting to travel in quieter months means you'll typically find lower prices on flights and hotels.
How many days is enough for Summerland Key?
With a well-planned schedule, you can easily hit the most popular Summerland Key sights in a few days. But if you'd like to discover lesser-known spots or go on day tours, consider booking your Summerland Key vacation for longer.
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. Pick your dates: The things you plan to do in Summerland Key and your preferred season can help you decide when to travel.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and airfares. Your hotel will likely be the largest expense during your trip to Summerland Key.
  3. Use Expedia's trip planning tool to explore Summerland Key: Research every part of your trip to Summerland Key with this comprehensive planner. Invite your family and friends to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how many days away: Start by listing all the sights and activities you want to experience in Summerland Key. Then, estimate how long you'll need for each, along with any travel time.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalized Summerland Key vacation package.
  6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip in nature, you won't have to worry about missing out on Summerland Key's best offerings. Find all the fun things to do in Summerland Key with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Summerland Key vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Summerland Key trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.