Summerland Key Holidays from NZ$3,298
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 NZ$5,108, price is now NZ$3,298 per person
NZ$3,298
per person
2 Apr - 8 Apr
found 2 hours ago
Return flight included
Christchurch (CHC) 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
The Shelborne By Proper, a Member of Design Hotels
South Beach
Save 100% on your flight
Price was NZ$6,278, price is now NZ$4,023 per person
NZ$4,023
per person
19 Feb - 23 Feb
found 1 day ago
Return direct flight included
Auckland (AKL) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
The holding fee is ridiculously high
Reviewed on 8 Jan 2026
President Hotel
South Beach
Price was NZ$4,946, price is now NZ$3,364 per person
NZ$3,364
per person
2 Apr - 8 Apr
found 2 hours ago
Return flight included
Christchurch (CHC) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Overall is nice. However, i think it will be even better if there is toothbrush and paste
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
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! (1,007 reviews)
Clean room, great convenient location and amazing snorkeling trip! We will come back.
Reviewed on 3 Jan 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is NZ$461 per night from 11 Jan to 12 Jan
NZ$461
11 Jan - 12 Jan
includes taxes & fees
8.8/10 Excellent! (1,016 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 NZ$331 per night from 13 Jan to 14 Jan
NZ$331
13 Jan - 14 Jan
includes taxes & fees
8/10 Very Good! (1,005 reviews)
The room was spacious well proportioned very clean and friendly staff only drawback was no coffee pot in the room
Reviewed on 1 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
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
NZ$47
per adult
90% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
NZ$99
per adult
88% of travellers recommend
Explore a world of travel with Expedia
- Apartments in Sugarloaf Key
- Cottages in Cudjoe Key
- Resort in Little Torch Key
- Caravan Parks in Boca Chica Key
- Motels in Lower Keys
- Resort in Lower Keys
- Resort in Lower Florida Keys
- Caravan Parks in Lower Florida Keys
- Hostels in Lower Florida Keys
- Motels in Lower Florida Keys
- Villas in Bahia Honda Key
- Lodges in Bahia Honda Key
- Resort in Bahia Honda Key
- Hersha Hospitality Hotels in Lower Florida Keys
- Beach Hotels in Boca Chica Key
- Cheap Hotels in Boca Chica Key
- Beach Hotels in Big Pine Key
- Spa Hotels in Big Pine Key
- Cheap Hotels in Big Pine Key
- Golf Hotels in Little Torch Key
- Cheap Hotels in Lower Florida Keys
- Luxury Hotels in Lower Florida Keys
- Beach Hotels in Lower Florida Keys
- Hotels with Pool in Lower Florida Keys
- Cheap Hotels in Lower Sugarloaf Key
- Sugarloaf Shores Hotels
- Big Pine Key Hotels
- Hotels near Boca Chica Nude Beach
- Cow Key Hotels
- Hotels near Key West Visitors Center
- Hotels near Coupon Bight Aquatic Preserve
- Summerland Key Hotels
- Smathers Beach
- Southernmost Point
- Fort East Martello Museum and Gallery
- Key West Cemetery
- Clarence S. Higgs Memorial Beach Park
- Mel Fisher Maritime Museum
- Boca Chica Nude Beach
- Big Pine Key Holidays
- Coco Plum Beach
- Mallory Square
- Pigeon Key
- Fort Zachary Taylor Historic State Park
- Key West Holidays
- Key West Butterfly and Nature Conservatory
- Florida Keys Beaches
- Duval Street
- Crane Point Museum and Nature Center
- South Beach
- Visit Big Torch Key
- Visit Port Pine Heights
- Visit Eden Pines
- Visit Lower Florida Keys
- Visit Big Pine Key
- Visit Sugarloaf Shores
- Visit Cudjoe Key
- Visit Melody Key
- Visit Ramrod Key
- Orlando Rental Cars in Bahia Honda Key
- Island Car Rentals Rental Cars in Bahia Honda Key
- Airport Van Rental Rental Cars in Bahia Honda Key
- Thrifty Car Rental Rental Cars in Lower Sugarloaf Key
- Avis Rental Cars in No Name Key
- Ace Rental Cars in No Name Key
- United Rental Cars in Sugarloaf Key
- Airport Van Rental Rental Cars in Sugarloaf Key
- Thrifty Car Rental Rental Cars in Melody Key
- Hertz Rental Cars in Lower Florida Keys
- Avis Rental Cars in Lower Florida Keys
- Budget Rental Cars in Lower Florida Keys
- Ace New Zealand Rental Cars in Lower Florida Keys
- Island Car Rentals Rental Cars in Lower Florida Keys
- Fox Rental Cars Rental Cars in Lower Florida Keys
- National Car Rental Rental Cars in Lower Florida Keys
- Global Rent a Car Rental Cars in Lower Florida Keys
- United Rental Cars in Lower Florida Keys
- Dollar Rent A Car Rental Cars in Lower Florida Keys
- Discount Car Rentals Rental Cars in Lower Keys
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
