Summerland Key Vacations from $278

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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.
Iberostar Waves Berkeley Shore

Iberostar Waves Berkeley Shore

4 out of 5
South Beach
Save 100% on your flight
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
8.8/10 Excellent! (1,342 reviews)
Property staff were really friendly and accommodating! I had a late flight and they gave me a check out as a courtesy. Room really clean.

Reviewed on Jul 13, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Beautiful art deco room. Wonderful staff. Excellent location. Will stay here again. Only downfall I can say was no fresh coffee until 730.

Reviewed on Jul 13, 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
per person
Sep 18 - Sep 22
found 2 days ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Fave hotel in south beach! Clean, amazing amenities, and close to the best restaurants.

Reviewed on Jul 15, 2025

Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
9/10 Wonderful! (136 reviews)
Great place to stay, Convenient valet parking.

Reviewed on Jul 12, 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 Venture 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
$156 nightly
The price is $175 total per night from Aug 10 to Aug 11
$175 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (1,004 reviews)
"The private beach was incredible, staff was friendly. Didn't take advantage of the free breakfast but to even have the option was amazing. Bed was a little rickety but that if anything is my only critique."

Reviewed on Jul 9, 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 Aug 10 to Aug 11
$111 total
Aug 10 - Aug 11
Total includes taxes and fees
8/10 Very Good! (1,004 reviews)
"Pretty good"

Reviewed on Jul 13, 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! (405 reviews)
"The room was very clean and spacious. Loved the pool and beach areas."

Reviewed on Jul 12, 2025

Get rates
Sugarloaf Key Hotel at KOA Resort
See all 599 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.

Find the Best Summerland Key Vacation Packages

Summerland Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Max Temp Winter
75ºF
Max Temp Summer
85ºF
Top Sights
Bahia Honda State Park, Florida Keys Beaches and Calusa Beach

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Frequently asked questions

How much does a Summerland Key vacation package cost?
You'll find cheap prices from $278 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.