Summerland Key Vacations from $513

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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.
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,291, price is now $513 per person
$513
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
16/10 Exceptional! (1,003 reviews)
Enjoyed a few days with the kids gere

Reviewed on Nov 15, 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $2,365, price is now $1,022 per person
$1,022
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
18.8/10 Exceptional! (56 reviews)
Quiet, modern, and luxurious are what I would describe this beautiful resort. Even in the heart of south beach, you feel like you're

Reviewed on Nov 21, 2025

Canada House Pompano Beach

Canada House Pompano Beach

2 out of 5
Price was $1,378, price is now $599 per person
$599
per person
Feb 5 - Feb 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
18.4/10 Exceptional! (69 reviews)
The service was very nice. The walk to the beach was perfect .

Reviewed on Nov 11, 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 $16,385, price is now $7,321 per person
$7,321
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
16/10 Exceptional! (1 review)
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Price was $2,083, price is now $934 per person
$934
per person
Feb 12 - Feb 17
found 11 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
16.8/10 Exceptional! (829 reviews)
Rooms were clean and the staff were good as well.

Reviewed on Nov 19, 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

Upper Sugarloaf Key

4/5(21 reviews)

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

Upper Sugarloaf Key

Sugarloaf Beach

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

Sugarloaf Beach

What to do in Summerland Key

Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$45
per adult
88% of travellers recommend
Key West Conch Tour Train
We never take more than 6 people on-board to let you ENJOY your adventure!

Dolphin and Snorkel

$122
per adult
Dolphin and Snorkel
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
$137 nightly
The price is $154 total per night from Nov 30 to Dec 1
$154 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
The property is beautiful! Room was very small for two people with nowhere to place luggage (one bedside table between the two beds and an alcove with a microwave was all the extra space there was. The air conditioner was very loud, sounding like water was trapped in it. Alerted front desk upon check ...

Reviewed on Nov 18, 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 Nov 30 to Dec 1
$111 total
Nov 30 - Dec 1
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
A very well maintained older facility. Especially enjoyed the high vaulted ceiling on this 2nd floor unit

Reviewed on Nov 17, 2025

Sugar Loaf Lodge
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
$195 nightly
The price is $219 total per night from Nov 24 to Nov 25
$219 total
Nov 24 - Nov 25
Total with taxes and fees
7.4/10 Good! (1,003 reviews)
Room was really clean and receptionist very friendly. Travelling with my son so had a nice big bed each. Balcony was nice and its only 35 mins to Key West which was oerfect

Reviewed on Nov 9, 2025

Looe Key Reef Resort
See all 622 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 $513 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.

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