Summerland Key Holidays from AU$606

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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

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was AU$918, price is now AU$606 per person
AU$606
per person
27 Sept - 1 Oct
found 1 day ago
Return flight included
New York (NYC) to Miami (MIA)
8.6/10 Excellent! (1,009 reviews)
Park 15$ a day -

Reviewed on 13 July 2026

Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
South Beach
Save 100% on your flight
Price was AU$1,000, price is now AU$625 per person
AU$625
per person
27 Sept - 1 Oct
found 1 day ago
Return flight included
New York (NYC) to Miami (MIA)
9.4/10 Exceptional! (228 reviews)
Your staying here for the location. Very old Florida. The a/c was very loud and hard to sleep through and the bed was flimsey and uncomfortable. All the toiletries are in the lobby which if you dont know that can be annoying. There are two cats that roam around very cute. And an adorable area in the back perfect for reading or having a glass of wine.

Reviewed on 13 July 2026

Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Mid Beach
Save 100% on your flight
Price was AU$1,800, price is now AU$1,149 per person
AU$1,149
per person
27 Sept - 1 Oct
found 1 day ago
Return flight included
New York (NYC) to Miami (MIA)
8.6/10 Excellent! (1,415 reviews)
They have sunscreen and sunglass wipes by the pool and there are water stations throughout the hotel and they give you two free water bottles Evian per day and they have Nespresso coffee in the rooms and you can eat by the pool or Nobu or Ocean Social, gratuity is included 20%. Each room guests two lounge chairs by the beach for free and towels. Everything was great. We loved it.

Reviewed on 13 July 2026

Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
Price was AU$1,636, price is now AU$1,068 per person
AU$1,068
per person
27 Sept - 1 Oct
found 1 day ago
Return flight included
New York (NYC) to Miami (MIA)
8.6/10 Excellent! (3,309 reviews)
Beautiful and clean

Reviewed on 13 July 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
Price was AU$1,348, price is now AU$897 per person
AU$897
per person
27 Sept - 1 Oct
found 1 day ago
Return flight included
New York (NYC) to Miami (MIA)
8/10 Very good! (1,151 reviews)
la pisina estaba sucia los cuartos limpios pero la pisina un asco tuvimos 2 dias sin playa x el zargazo mas la pisina sucia horrible

Reviewed on 12 July 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
A calm lake with several white birds, including herons and pelicans, on the water's edge.

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.

Find hotels in Cutthroat Harbor Estates

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

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 AU$267 per night from 12 Aug to 13 Aug
AU$267
12 Aug - 13 Aug
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"We happened upon this quaint resort on a weekend to the Keys. What a great spot! It is not on one of the main keys but is close to Key West and other fun locations. The resort had hammocks to relax in, a pool, docks, outdoor activities and a small breakfast (don't plan on filling up on it if you ..."

Reviewed on 13 July 2026

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
9.8/10 Exceptional! (597 reviews)
"everything was awesome except the water amenities rental, until 3:00pm is too early."

Reviewed on 14 July 2026

Get rates
Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

3 out of 5
311 Johnson Rd Summerland Key FL
9.4/10 Exceptional! (19 reviews)
"The cabins were pretty much new. Beautiful views. Also the cabins are separate from RV area. Cant wait to go back. Lass that 1/2 hour to Key West. Way better price base foe better rooms and amenities."

Reviewed on 14 July 2026

Get rates
Sugarloaf Key RV Resort & Cottages
See all 624 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.
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Stay near popular Summerland Key attractions

Sugarloaf Beach

8.4/10 (38 reviews)
This secluded private beach on Sugarloaf Key offers a tranquil escape from the busier Florida Keys shorelines. Guests enjoy pristine views and peaceful sunbathing in a natural, amenity-light setting.
See properties

What to do in Summerland Key

Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

AU$80
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Kayak the mangrove tidal creeks

Key West Mangrove Kayak Eco Tour

AU$116
per adult
100% of travellers recommend
Key West Mangrove Kayak Eco Tour
Dolphin Watching and Snorkeling

Key West Dolphin & Snorkeling Tour - Small Group

AU$195
per adult
100% of travellers recommend
Key West Dolphin & Snorkeling Tour - Small Group
See all activities in Summerland Key

Frequently asked questions

How much does a Summerland Key holiday package cost?
You'll find cheap prices from AU$606 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.

Explore a world of travel with Expedia

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