
Summerland Key Holidays from NZ$2,702
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The Latest Summerland Key Holiday Deals
Price found within the past 48 hours. Click for updated prices.

Cavalier Hotel South Beach
South Beach
per person
12 Aug - 19 Aug
found 22 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Perfectly located on Ocean Drive with an old-school Art Deco vibe that feels both historic and fresh. The room was spotless, the A/C was ice cold, and the bed was genuinely comfortable. Staff was friendly and helpful. You’re across from the beach, but it still feels like a quiet escape. Would absolutely stay here again.
Reviewed on 1 Jul. 2025



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 Venture Key.
Summerland Key Holiday
Our pick of the best Summerland Key Hotel Deals

Parmer's Resort
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$290 per night from 10 Aug to 11 Aug
NZ$290
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"The private beach was incredible, staff was friendly. Didn't take advantage of the free breakfast but to even have the option was amazing. Bed was a little rickety but that if anything is my only critique."
Reviewed on 9 Jul. 2025

Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939, Summerland Key, FL
9.6/10 Exceptional! (403 reviews)
"Hands down my favorite resort in all of the Florida Keys. Awesome location, great staff, and the resort overall is breathtaking. Only a 25 minute drive to Key West which is a huge plus. Definitely worth every penny!"
Reviewed on 7 Jul. 2025

Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is NZ$222 per night from 11 Aug to 12 Aug
NZ$222
11 Aug - 12 Aug
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Close to all the activities we wanted to do. Older property but room was big and comfortable."
Reviewed on 6 Jul. 2025
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

Full Day Charter Snorkeling Sandbar and Eco Safari Adventure
NZ$1,498
per traveller

Half Day Charter Sandbar Snorkeling and Eco Adventure
NZ$1,248
per traveller
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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.