Summerland Key Holidays from AU$1,044

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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.
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
21 Feb - 24 Feb
found 1 day ago
Return flight included
New York (LGA) to Miami (MIA)
8.4/10 Very Good! (729 reviews)
I will definitely be staying here again

Reviewed on 4 Jan. 2025

The Balfour Hotel

The Balfour Hotel

4 out of 5
South Beach
Save 100% on your flight
per person
21 Feb - 24 Feb
found 1 day ago
Return flight included
New York (LGA) to Miami (MIA)
8.4/10 Very Good! (678 reviews)
The property is just what you would expect for this area, the room was small but as are most rooms on this area. We really liked how quiet it was yet close to all the action and the walk to the beach was so easy and great amenities to have two chairs and an umbrella included in the room rental. Staff was so kind!

Reviewed on 11 Jan. 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
21 Feb - 24 Feb
found 1 day ago
Return flight included
New York (LGA) to Miami (MIA)
9.2/10 Wonderful! (1,054 reviews)
This is by far the best hotel I’ve stayed at in South Beach. The amenities are exceptional, the staff goes above and beyond with their friendliness, and every detail is thoughtfully designed for relaxation and enjoyment. It’s the perfect place to have the best possible time. Highly recommend!

Reviewed on 14 Jan. 2025

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
21 Feb - 24 Feb
found 1 day ago
Return flight included
New York (LGA) to Miami (MIA)
8/10 Very Good! (1,007 reviews)
Beautiful boutique hotel steps to th beach. Got a very cool vibe, Would stay here again

Reviewed on 14 Jan. 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
21 Feb - 24 Feb
found 1 day ago
Return flight included
New York (LGA) to Miami (MIA)
8.2/10 Very Good! (1,114 reviews)
centrally located, convenient to all stores, restaurants, closed to public parking. Room is spacious, staff was very helpful. Is simple, and affordable.

Reviewed on 14 Jan. 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
Default Image

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

Looe Key Reef Resort
Looe Key Reef Resort
2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$316 per night from 16 Jan to 17 Jan
AU$316
includes taxes & fees
16 Jan - 17 Jan
7.4/10 Good! (1,002 reviews)
"Nice and quiet very comfortable and great restaurant and bar"

Reviewed on 31 Dec. 2024

Looe Key Reef Resort
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$399 per night from 26 Jan to 27 Jan
AU$399
includes taxes & fees
26 Jan - 27 Jan
8.8/10 Excellent! (1,001 reviews)
"This is an older property, likely developed in the 60’s. We were greeted warmly despite our early arrival. We stayed in a double twin room named “Tuna.” On entering the space there was a strong smell of cleanser. It adjoined two lodging areas on either side. We were able to hear a bit of conversation ..."

Reviewed on 12 Jan. 2025

Parmer's 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 AU$362 per night from 20 Jan to 21 Jan
AU$362
includes taxes & fees
20 Jan - 21 Jan
8/10 Very Good! (998 reviews)
"Everything was good"

Reviewed on 6 Jan. 2025

Sugar Loaf Lodge
See all 582 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Summerland Key holiday package cost?
You’ll find cheap prices from AU$1,044 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.

What to do in Summerland Key

A fun-filled adventure for the whole family

Guided Clear Kayak Eco-Tour Near Key West

AU$127
per adult
Guided Clear Kayak Eco-Tour Near Key West
Half Day Charter Sandbar Snorkeling and EcoTour Adventure

Half Day Charter Sandbar Snorkeling and Eco Adventure

AU$1,209
per traveller
Half Day Charter Sandbar Snorkeling and Eco Adventure
Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

AU$1,075
per traveller
Marathon Backcountry Fishing Charter
See all activities in Summerland Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.