Summerland Key Vacation Packages

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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!

Top Summerland Key Vacation Deals

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

The Marlin Hotel

4 out of 5
South Beach
Price was CA $1,600, price is now CA $939 per person
CA $939
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
The location was great, the bar convenient, the restaurant downstairs was great. Overnight parking was reasonable.

Reviewed on Aug 2, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $19,630, price is now CA $8,144 per person
CA $8,144
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
5.8/10 (326 reviews)
Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No beach chair, no wagon and the umbrella covered 1 person. I reached out to the person but never showed up with clean sheets. I had to invest in my stay detergent, sanitizing wipes, trash bags and toilet covers. Let me know forget to say, on my first stay the bottom of my feet was all black from the floors being super dirty. The only good thing of the place was the beach distance.

Reviewed on Jul 23, 2026

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 CA $29,455, price is now CA $15,809 per person
CA $15,809
per person
Sep 3 - Sep 9
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was CA $4,467, price is now CA $2,593 per person
CA $2,593
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,571 reviews)
Everything was Amazing!

Reviewed on Aug 2, 2026

Viscay Hotel

Viscay Hotel

2.5 out of 5
South Beach
Price was CA $3,470, price is now CA $2,052 per person
CA $2,052
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very good! (341 reviews)
Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand

Reviewed on Jul 16, 2026

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
A calm lake with several white birds, including herons and pelicans, on the water's edge.

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

Ready to book your vacation to Summerland Key?

 

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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
The price is CA $153 per night from Aug 12 to Aug 13
CA $153
CA $217 total
Aug 12 - Aug 13
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"I nice and quiet place The staff is very nice"

Reviewed on Aug 2, 2026

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
9.8/10 Exceptional! (611 reviews)
"Overall it was a great experience. All staff is really kind. Our room had dogs hair on the floor when I first swept and bed isn’t too comfortable but room overall looks beautiful and is well maintained. Bar and pool close a bit early but like everything else in the keys. Only annoying thing is marina ..."

Reviewed on Jul 29, 2026

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Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

3 out of 5
311 Johnson Rd Summerland Key FL
Get rates
Sugarloaf Key RV Resort & Cottages
See all 625 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Summerland Key attractions

Sugarloaf Beach

8.4/10 (38 reviews)
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
See properties

What to do in Summerland Key

Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

CA $63
per adult
88% of travellers recommend
Key West Conch Tour Train
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

CA $39
per adult
Full Day Trip in Key West from Miami
See all activities in Summerland Key

Frequently asked questions

How much does a Summerland Key vacation package cost?
Offering great value package deals from CA $939 on Expedia, you'll be pleasantly surprised at how much a vacation to Summerland Key costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Summerland Key?
If you're looking to book a cheap Summerland Key vacation package, consider travelling in September, October and November. You'll typically find better rates on hotels and airfares during these months — ideal for a budget-friendly break.
How many days is enough for Summerland Key?
We'd suggest booking a Summerland Key vacation for a minimum of 4 days. This gives you plenty of time to tick off top attractions including Blue Hole and Cook Island, and also explore neighbourhoods like Eden Pines and Cutthroat Harbour Estates. You could even squeeze in a day trip (or two) from Summerland Key.
How to find the best Summerland Key package deals?
Use Expedia's filter tool to find some terrific Summerland Key package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Summerland Key package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Summerland Key vacation as a package?
You can enjoy significant savings on your Summerland Key retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Summerland Key?
If you're considering an impromptu Summerland Key getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
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 get away.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will likely be the largest expense during your trip to Summerland Key.
  3. Decide how long to go for: Now that you know more about Summerland Key, you can work out the perfect length of your vacation. Create a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Summerland Key vacation package that brings all your bookings together.

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