Summerland Key Holidays from NZ$4,048
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 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.
Oceans Edge Key West Resort, Hotel & Marina
Price was NZ$4,749, price is now NZ$4,048 per person
NZ$4,048
per person
28 July - 31 July
just found
Return flight included
Auckland (AKL) to Key West (EYW)
9/10 Wonderful! (1,865 reviews)
Parking is not included in the stand and there are a lot of other fees that should be included. I wound up paying $375 more just to cover all the fees. Including a 29 dollar a day parking fee. Why is that not included. That was disappointing and the resort is in a weird part of town. Overall I would not stay there again.
Reviewed on 31 May 2026
The Key West Hotel
Key West Historic District
Price was NZ$5,180, price is now NZ$4,244 per person
NZ$4,244
per person
28 July - 31 July
just found
Return flight included
Auckland (AKL) to Key West (EYW)
9.2/10 Wonderful! (556 reviews)
Our room was spacious and clean, with a bag of Key Lime cookies waiting for us on arrival. We appreciated boxed instead of bottled water that was always available in-room at no extra cost. But the thing we enjoyed most was the secluded Bali Bar, which was hidden away from busy Duvall Street. The live music was excellent and the. bar tenders were very accommodating. There are many hotels and places to stay in Key West but we would definitely return to this one. Highly recommend!
Reviewed on 18 May 2026
Coconut Beach Resort
Old Town Key West
Price was NZ$5,061, price is now NZ$4,225 per person
NZ$4,225
per person
28 July - 31 July
just found
Return flight included
Auckland (AKL) to Key West (EYW)
8.8/10 Excellent! (190 reviews)
This was a great place to stay! Clean and well-placed on Key West. Pool and patio were great for getting some sun.
Reviewed on 29 May 2026
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Price was NZ$5,358, price is now NZ$4,494 per person
NZ$4,494
per person
28 July - 31 July
just found
Return flight included
Auckland (AKL) to Key West (EYW)
8.6/10 Excellent! (371 reviews)
Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with just a little more attention to detail
Reviewed on 18 May 2026
Hyatt Vacation Club at Windward Pointe, Key West
Price was NZ$5,199, price is now NZ$4,382 per person
NZ$4,382
per person
28 July - 31 July
just found
Return flight included
Auckland (AKL) to Key West (EYW)
9.4/10 Exceptional! (1,098 reviews)
The room and balcony were fantastic. The pool, grounds, and view of the ocean were lovely. The staff was super welcoming and friendly when we arrived. We enjoyed the close restaurant and walking path right across the street.
Reviewed on 28 May 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 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$391 per night from 7 June to 8 June
NZ$391
7 June - 8 June
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"What a beautiful, relaxing property. It's a gem, full of great things to do or a little bit of beach time. The staff was very helpful and friendly."
Reviewed on 30 May 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9.8/10 Exceptional! (7 reviews)
"I prefer Communication via email or text. This was the plus for me with the resort. It was very easy to check in after hours and the reach the resort. Welcome package with all you need to get to the cottage. Beautiful, clean and just ready to start your vacation. This place is 25 min from Key West! ..."
Reviewed on 26 May 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
NZ$93
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
NZ$46
per adult
88% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
NZ$117
per adult
76% 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.
