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.
May-Dee Suites

May-Dee Suites

2.5 out of 5
Hollywood Hills
Save 100% on your flight
per person
Jul. 5 - Jul. 10
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9.2/10 Wonderful! (1,275 reviews)
It was wonderful to have a full kitchen and living space. The management and staff were very friendly and accommodating. Will definitely be staying here again!

Reviewed on May 14, 2024

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Jul. 22 - Jul. 27
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9/10 Wonderful! (1,006 reviews)
Awesome Hotel.. multiple pools with a roof top pool and restaurant that’s a must see

Reviewed on May 20, 2024

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
Aug. 2 - Aug. 7
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Mayfair House Hotel & Garden

Mayfair House Hotel & Garden

4.5 out of 5
Coconut Grove
Save 100% on your flight
per person
Jul. 22 - Jul. 27
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9/10 Wonderful! (502 reviews)
Beds are so comfy and everything just so perfect. The only thing missing is a fridge. Everything else is amazing

Reviewed on May 22, 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. 14 - Jul. 19
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very Good! (1,017 reviews)
They make it seem like there’s multiple dining options but there’s one menu and you can eat from it in different locations. The pool was very small. There was beach access which was probably the best thing. Otherwise for the price stay down the road at one of the multiple nicer hotels with more options.

Reviewed on May 21, 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! (144 reviews)
"Really enjoyed our week stay. Suites are clean and everything is in good condition. Great for an extended stay. They don't supply a regular coffee maker so we brought our own. They have a Keurig type. Otherwise all that we needed was there."

Reviewed on May 19, 2024

Get rates
Sugarloaf Key Hotel at KOA Resort
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 $217 per night from Jun. 9 to Jun. 10
CA $217
CA $288 total
includes taxes & fees
Jun 9 - Jun 10
8.6/10 Excellent! (1,000 reviews)
"Clean and tidy, good facilities, lovely beach area and views."

Reviewed on May 13, 2024

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 $230 per night from Jun. 6 to Jun. 7
CA $230
CA $259 total
includes taxes & fees
Jun 6 - Jun 7
8/10 Very Good! (998 reviews)
"Room clean"

Reviewed on May 13, 2024

Sugar Loaf Lodge
See all 555 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 $482, 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

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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.