Summerland Key Holidays from AU$2,102
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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.
Cavalier Hotel South Beach
South Beach
Price was AU$3,331, price is now AU$2,102 per person
AU$2,102
per person
1 Mar - 7 Mar
found 1 day ago
Return flight included
Houston (IAH) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Main road in front of hotel was closed. When we arrived, the concierge had no idea where to tell us to park.
If they were transparent about it, ok. I would be ok. Then they said they are out of the 'free' wine, but could charge me $8 for a Heineken. Then couldn't get the elevator to work (we were on the 2nd floor thank God)
The room was in good shape. The parking is what set off the chain for me. It's not hard to update a website. Or at least tell your staff what to say. Ended up parking in the City parking garage. I'd give it like a 75/100.
Reviewed on 6 Jan 2026
1 Hotel South Beach
South Beach
Save 100% on your flight
Price was AU$10,902, price is now AU$6,600 per person
AU$6,600
per person
1 Mar - 7 Mar
found 1 day ago
Return flight included
Houston (IAH) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
The best hotel hands down in south Miami.
Reviewed on 8 Jan 2026
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
Cutthroat Harbor Estates
While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Out Keys and Upper Sugarloaf Key.
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
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
7.4/10 Good! (1,002 reviews)
Staff was friendly. Room was clean. Furniture a little worn but bed comfortable and clean linens
Reviewed on 8 Jan 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is AU$396 per night from 13 Jan to 14 Jan
AU$396
13 Jan - 14 Jan
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Excellent
Reviewed on 5 Jan 2026
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is AU$284 per night from 13 Jan to 14 Jan
AU$284
13 Jan - 14 Jan
includes taxes & fees
8/10 Very Good! (999 reviews)
Great staff and great location!
Reviewed on 7 Jan 2026
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.
What to do in Summerland Key
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
AU$86
per adult
88% of travellers recommend
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
AU$179
per adult
98% of travellers recommend
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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.
