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 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
Jul. 2 - Jul. 6
Roundtrip flight included
Toronto (YTO) 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
Jul. 2 - Jul. 6
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (1,012 reviews)
Such a wonderful stay! Hotel was gorgeous & staff was phenomenal. Can’t wait to come back!

Reviewed on Apr. 30, 2024

Holiday Isle Yacht Club

Holiday Isle Yacht Club

2.5 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jul. 11 - Jul. 16
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9.2/10 Wonderful! (70 reviews)
Perfect place! The best place we have stayed in the Fort Lauderdale area. Very comfortable, clean, easy going and great people! We highly recommend!

Reviewed on Feb. 18, 2024

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jul. 11 - Jul. 16
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.4/10 Very Good! (1,012 reviews)
Unique was the size of the rooms. Comfortable. Beautiful roof top setting for the wedding we attended

Reviewed on Apr. 30, 2024

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
May 31 - Jun. 3
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
A very old but clean place. Rooms are small but comfortable. Public parking lot conveniently directly behind the hotel. Free breakfast was amazingly good! Staff are friendly and really keep the place clean.

Reviewed on Apr. 30, 2024

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
Sugarloaf Shores featuring a bay or harbor

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

Find hotel + flight trips in Sugarloaf Shores

Summerland Key Hotel Deals

Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key Hotel at KOA Resort
2 out of 5
251 Co Rd 939, Summerland Key, FL
9.6/10 Exceptional! (121 reviews)
"The unit was clean and recently updated. We had a view of the water. It is about 20 minutes north of Key West. They have a beach area, swimming pool, hot tub, and cafe onsite."

Reviewed on Apr. 25, 2024

Get rates
Sugarloaf Key Hotel at KOA 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 $231 per night from May 8 to May 9
CA $231
CA $260 total
includes taxes & fees
May 8 - May 9
8/10 Very Good! (998 reviews)
Excellent
"We have a wonderful stay quite and super nice"

Reviewed on Apr. 27, 2024

Sugar Loaf Lodge
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 $191 per night from May 12 to May 13
CA $191
CA $260 total
includes taxes & fees
May 12 - May 13
8.6/10 Excellent! (998 reviews)
Nice little resort
"This is a nice little group of older buildings right on Little Torch Key. Not too fancy but you have a pool, some little piers and even a boat launch. This is not ocean it's water between keys so no surf and mostly coral but a little sand on their beach for getting feet wet. Staff is friendly, they ..."

Reviewed on Apr. 29, 2024

Parmer's Resort
See all 563 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Summerland Key vacation package cost?
Less than you might think — from a low CA $630, in fact! By bundling hotels, flights and car rentals into a custom-built travel package, your getaway to Summerland Key is just clicks away.
How do I get a cheap travel package to Summerland Key?
Bundle your bookings with Expedia to save big on your next big adventure. With over 550 air carriers and 1,000,000 properties around the globe, your Summerland Key vacation package can be customized exactly to suit your travel style. With all that extra money, why not throw in a few fun tours and activities? It’s an easy way to unlock even more bargains. That vacation you’ve always dreamed of in Summerland Key is closer than you thought!
What are the top hotels in Summerland Key?
Summerland Breeze - Three House Retreat and Summerland Cove Paradise Waterfront Deep Water Canal are a couple of the most popular hotels in Summerland Key. Why not have a look at the amenities and facilities at each and then decide?
How far in advance should I book my Summerland Key vacation?
To bag discount prices, book nice and early. Airlines generally advertise flight tickets, along with some of the lowest fares, around 12 months prior to departure. Hotels, car rental and activities should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway to Summerland Key, there are always plenty of great bargains to be had on Expedia. Book something in today!
What does an Expedia Summerland Key travel package include?
Travel packages include flights, rental cars and hotels, but you can combine any of them to create your dream Summerland Key escape. You can also add on activities and experiences once you’ve made your booking. You’re in control! When you combine your bookings with Expedia, you’ll get discounts you won’t find anywhere else.
What should I know before booking a Summerland Key travel package?
Tailor deals to suit your budget with an Expedia package. Hotels, flights, rental cars — we’re a one-stop shop for all of them. You’ll save a tidy sum just by combining your bookings. Whether you’re heading away on an adventure in the snow or relaxing on a sunny beach, your dream getaway is only clicks away.
Can I choose my airline with a Summerland Key Expedia vacation package?
Yes, you’re in control. Expedia has access to more than 550 airlines around the world, so you can customize your Summerland Key getaway according to your travel preferences.
If I'm not able to travel, can I cancel my Summerland Key vacation package?
Don’t stress if you’re rethinking your Summerland Key vacation package — it’s possible to change or amend your booking. And if you’ve booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We realize life can occasionally throw a spanner in the travel works, so look up our Customer Service Portal if that occurs. When you’re ready to make changes, we’re here to help.

Discover the most popular places to visit in Summerland Key

Image for 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
Image for Sugarloaf Beach

Sugarloaf Beach

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

Sugarloaf Beach
Image for Upper Sugarloaf Key

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

Image for Half Day Charter Sandbar Snorkeling and EcoTour Adventure

Half Day Charter Sandbar Snorkeling and EcoTour Adventure

CA $1,016
Per adult
Half Day Charter Sandbar Snorkeling and EcoTour Adventure
Image for Full Day Charter Snorkeling Sandbar and Eco Safari Adventure

Full Day Charter Snorkeling Sandbar and Eco Safari Adventure

CA $1,219
Per adult
Full Day Charter Snorkeling Sandbar and Eco Safari Adventure
Image for Guided Clear Kayak Eco-Tour Near Key West

Guided Clear Kayak Eco-Tour Near Key West

CA $102
Per adult
Guided Clear Kayak Eco-Tour Near Key West
See all activities in Summerland Key

Other vacations you might like

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