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

Cavalier Hotel South Beach

3.5 out of 5
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

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
per person
12 Aug - 19 Aug
found 22 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
9.2/10 Wonderful! (181 reviews)
Super clean and modern rooms. Beautiful rooftop to hang out as well too.

Reviewed on 9 Jul. 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
per person
12 Aug - 19 Aug
found 22 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
The property need more fine dining and the walk btw locations long to large for my taste

Reviewed on 10 Jul. 2025

President Hotel

President Hotel

3.5 out of 5
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! (1,596 reviews)
Henry was amazing and very accommodating. The room was clean and the staff was very nice.

Reviewed on 11 Jul. 2025

iCoconutGrove Vacation Rentals

iCoconutGrove Vacation Rentals

4 out of 5
Coconut Grove
per person
12 Aug - 19 Aug
found 22 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
9.2/10 Wonderful! (1,003 reviews)
Clean , wonderful room with kitchen. Splendid balcony view.

Reviewed on 11 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
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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.

Find hotels in Cutthroat Harbor Estates

Summerland Key Holiday

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 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

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! (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

Get rates
Sugarloaf Key Hotel at KOA Resort
Sugar Loaf Lodge
Sugar Loaf Lodge
2.5 out of 5
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

Sugar Loaf Lodge
See all 594 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.

What to do in Summerland Key

A fun-filled adventure for the whole family

Guided Clear Kayak Eco-Tour Near Key West

NZ$132
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

NZ$1,498
per traveller
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

NZ$1,248
per traveller
Half Day Charter Sandbar Snorkeling and Eco Adventure
See all activities in Summerland Key

Frequently asked questions

How much does a Summerland Key holiday package cost?
You'll find cheap prices from NZ$2,702 on Expedia for your Summerland Key break. However, factors like the season, length of stay and your choice of hotel will determine how much your holiday to Summerland Key costs.
What are the cheapest months to go to Summerland Key?
If you're hoping to score a cheap Summerland Key holiday package, consider travelling in September, October and November. You'll typically find lower rates on accommodation and flights during these quieter months --- ideal for a budget-friendly break.
How many days is enough for Summerland Key?
Generally, a handful of days is enough to tick off the major attractions during your Summerland Key holiday. However, if you'd like to have some time to relax or go on day trips, think about extending your trip.
How to find the best Summerland Key package deals?
Begin your search for a Summerland Key package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Summerland Key package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Summerland Key escape off to a flying start.
Is it cheaper to book a Summerland Key holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking stays and flights separately. Better still, you can customise your Summerland Key escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Summerland Key?
If you've got your Summerland Key holiday dates confirmed, book as soon as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Summerland Key?

  1. Choose when to go: Check your calendar and pack your bags. Your favourite season and the activities available will also help you decide when to holiday in Summerland Key.
  2. Set a budget: Factor in costs such as transportation, flights and meals when calculating how much to save for your trip to Summerland Key. Then, choose a hotel that suits your budget, whether that's an economical stay or a swankier getaway.
  3. Decide how long to go away for: Now that you're more familiar with Summerland Key, you can figure out the ideal length of your holiday. Put together a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customised Summerland Key holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.