Summerland Key Holidays from AU$5,832

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Your Summerland Key Holiday

Say bye-bye to planning worries and hello to a Summerland Key holiday package. With everything organised before you go, you can focus on discovering this city, starting with Breezeswept Beach Estates, which is good for adventure sports, fishing and watersports. Like to explore your new surroundings? Big Pine Key Flea Market, Cook Island and Blue Hole are some of the top places to visit during a trip to Summerland Key. That dream Summerland Key holiday is only clicks away. Browse accommodation, flights and more on Expedia for a trip that's tailored just for you.

The Latest Summerland Key Holiday Deals

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

Henrosa Hotel

3.5 out of 5
South Beach
per person
6 Jan - 13 Jan
found 6 hours ago
Return flight included
Sydney (SYD) to Miami (MIA)
8.2/10 Very Good! (694 reviews)
Charming boutique hotel. Staff were very pleasant. Shower and the bath products were terrific.

Reviewed on 19 Nov. 2024

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
6 Jan - 13 Jan
found 7 hours ago
Return flight included
Sydney (SYD) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
Beautiful property with very nice amenities and easy access to the beach. I highly recommend this place and look forward to coming back.

Reviewed on 24 Nov. 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
Save 100% on your flight
per person
6 Jan - 13 Jan
found 6 hours ago
Return flight included
Sydney (SYD) to Miami (MIA)
8/10 Very Good! (1 review)
Carillon Miami Wellness Resort

Carillon Miami Wellness Resort

5 out of 5
North Beach
per person
6 Jan - 13 Jan
found 6 hours ago
Return flight included
Sydney (SYD) to Miami (MIA)
8.8/10 Excellent! (674 reviews)
Great hotel with amazing exercise options

Reviewed on 24 Nov. 2024

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
per person
6 Jan - 13 Jan
found 7 hours ago
Return flight included
Sydney (SYD) to Miami (MIA)
9/10 Wonderful! (2,684 reviews)
Excellent hotel definitely my favorite in Miami

Reviewed on 21 Nov. 2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Our guide on 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
Default Image

Sugarloaf Shores

Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.

Find hotel + flight trips in Sugarloaf Shores

Summerland Key Holiday

Summerland Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Max Temp Winter
24ºC
Max Temp Summer
29ºC
Top Sights
Bahia Honda State Park, Florida Keys Beaches and Calusa Beach

Our pick of the best 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 AU$249 per night from 1 Dec to 2 Dec
AU$249
includes taxes & fees
1 Dec - 2 Dec
8.8/10 Excellent! (1,000 reviews)
"One of the BEST stays in a hotel/resort I have had in a long time. Absolutely perfect! Both check in and check out hosts were amazing, room was VERY clean and comfortable, grounds were clean, peaceful and the beach on the property gave great views. Any time I come down, this will be my choice for ..."

Reviewed on 16 Nov. 2024

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
9.6/10 Exceptional! (268 reviews)
"Beautiful Beautiful place"

Reviewed on 20 Nov. 2024

Get rates
Sugarloaf Key Hotel at KOA Resort
Looe Key Reef Resort
Looe Key Reef Resort
2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$210 per night from 2 Dec to 3 Dec
AU$210
includes taxes & fees
2 Dec - 3 Dec
7.4/10 Good! (1,000 reviews)
"Great place to stay in the Keys."

Reviewed on 14 Nov. 2024

Looe Key Reef Resort
See all 586 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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Summerland Key holiday package cost?
Less than you might think — from a low AU$5,832, 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 holiday 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 holiday 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 holiday?
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 holiday 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 holiday package?
Don’t stress if you’re rethinking your Summerland Key holiday 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 realise 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.

What to do in Summerland Key

A fun-filled adventure for the whole family

Guided Clear Kayak Eco-Tour Near Key West

AU$120
Per adult
Guided Clear Kayak Eco-Tour Near Key West
Full Day Charter Snorkeling Sandbar and Eco Safari Adventure

Full Day Charter Snorkeling Sandbar and Eco Safari Adventure

AU$1,367
Per adult
Full Day Charter Snorkeling Sandbar and Eco Safari Adventure
Half Day Charter Sandbar Snorkeling and EcoTour Adventure

Half Day Charter Sandbar Snorkeling and Eco Adventure

AU$1,139
Per adult
Half Day Charter Sandbar Snorkeling and Eco Adventure
See all activities in Summerland Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.