Summerland Key Vacations from $336

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Your Summerland Key Vacation

The hassle-free way to experience this vibrant city is with a tailor-made Summerland Key vacation package. Stay in the neighborhood of Breezeswept Beach Estates, which is great for watersports, adventure sports and fishing or choose someplace else — our packages are all about you. Make your trip to Summerland Key even more enjoyable by going sightseeing. Cook Island, Big Pine Key Flea Market and Blue Hole are among the major attractions worth exploring. A few clicks is all it takes to craft your dream Summerland Key vacation on Expedia.

The Latest Summerland Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Beachcomber Resort & Club

Beachcomber Resort & Club

4 out of 5
Save 100% on your flight
per person
Aug 9 - Aug 13
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9/10 Wonderful! (1,372 reviews)
I cannot wait to return! The hotel is in a perfect location - quiet, right on the beach and priced right. There are two pools that get plenty of sun and it was quiet at night when I wanted to get some sleep. Highly recommend!

Reviewed on May 16, 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
Jul 1 - Jul 5
Roundtrip flight included
Newark (EWR) 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 24 - Jul 28
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9/10 Wonderful! (1,002 reviews)
Beach was clean, compare to other resorts with private beach in miami!!! However we notice that all pool area were small for hotel quality 😉

Reviewed on May 13, 2024

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
per person
Jun 21 - Jun 25
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Nice little hotel steps from the beach. Staff is friendly and accommodating. It's an older building so the elevator is a bit janky. The breakfast was pretty meh but that shouldn't be a deal breaker. I would stay here again.

Reviewed on May 11, 2024

Ocean Villas of Deerfield

Ocean Villas of Deerfield

2.5 out of 5
Save 100% on your flight
per person
Jul 23 - Jul 30
Roundtrip flight included
New York (JFK) to Miami (MIA)
9.2/10 Wonderful! (1,003 reviews)
Very large rooms and immaculately clean. My only issue was the noise, especially from motorcycles racing up and down the street. There’s also the conversations outside your door. Having chairs out there does not help this at all. I also observed the staff: manager and maintenance people yelling back and forth….not very restful on one’s vacation. Seemingly oblivious to the fact that someone is paying to stay there!

Reviewed on May 15, 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 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

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! (137 reviews)
I’ll Be Back!!
"My stay was exceptional. The suite was spacious and decorated in the coastal style I love. Sunrise views from porch. The management went over and above to accommodate my need to change check in/out dates. The amenities were first class. So glad I chose to stay 20 miles from Key West, going in for ..."

Reviewed on May 11, 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 $134 per night from May 27 to May 28
$134
$184 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (998 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 $169 per night from May 19 to May 20
$169
$190 total
includes taxes & fees
May 19 - May 20
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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Summerland Key vacation package cost?
Less than you might think — from a low $336, 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

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

What to do in Summerland Key

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

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

$42
Per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Image for Full Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

$58
Per adult
Full Day Trip in Key West from Miami
Image for Day Trip to Key West with 3 hour Snorkeling & Open Bar

Day Trip to Key West with 3 hour Snorkeling & Open Bar

$129
Per adult
Day Trip to Key West with 3 hour Snorkeling & Open Bar
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.