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.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Overall, the property is great and it’s very close to the beach , the Check in staff was great and friendly. And the bedrooms are renovated very good . However, the bathroom has a sliding door which is glass when you are in the bathroom, your shadow can be seen by the person that is in the bedroom.

Reviewed on Jul. 23, 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 13 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1 review)
The Gabriel Miami South Beach, Curio Collection by Hilton

The Gabriel Miami South Beach, Curio Collection by Hilton

4 out of 5
South Beach
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (877 reviews)
Wonderful property and right in the middle of all the action in South Beach. Awesome they had two pools, one in courtyard then an amazing rooftop pool with incredible views! Bathrooms were nice and clean up on rooftop too! Only complaint would be room was pretty hot even with AC, just can’t seem to cool the room enough. Not sure if that’s extremely common for Miami since it’s so how they can’t keep up or what, but that was the same at another hotel we stayed downtown last year. Other than that, great hotel and would absolutely stay there again if going back to South Beach!

Reviewed on Jul. 20, 2025

Aloha Fridays

Aloha Fridays

3 out of 5
South Beach
per person
Oct 11 - Oct 18
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.4/10 Very Good! (36 reviews)
Best service at the restaurant

Reviewed on Jun. 8, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Good stay, hotel was accommodating whenever I needed something. Great location in south beach. Will be back

Reviewed on Jul. 20, 2025

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

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 $164 per night from Aug 24 to Aug 25
CA $164
CA $229 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Very nice place."

Reviewed on Jul. 19, 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 CA $135 per night from Aug 10 to Aug 11
CA $135
CA $152 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Good value
"I will stay here again. Good value. One of the biggest rooms I have ever stayed in."

Reviewed on Jul. 21, 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! (414 reviews)
"Great place to stay"

Reviewed on Jul. 21, 2025

Get rates
Sugarloaf Key Hotel at KOA Resort
See all 606 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

What to do in Summerland Key

12 hours Day at Key West With Boat Tour and Snorkeling

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

CA $38
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

CA $37
per adult
Full Day Trip in Key West from Miami
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

CA $62
per adult
88% of travellers recommend
Key West Conch Tour Train
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 $766 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.