Summerland Key Holidays

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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 Upper Sugarloaf 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$262 per night from 8 Sept to 9 Sept
NZ$262
8 Sept - 9 Sept
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Great place all around, will be going back in the future!"

Reviewed on 16 Aug. 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 NZ$190 per night from 1 Sept to 2 Sept
NZ$190
1 Sept - 2 Sept
includes taxes & fees
8/10 Very Good! (999 reviews)
"Great sleep"

Reviewed on 20 Aug. 2025

Sugar Loaf Lodge
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 NZ$595 per night from 20 Sept to 21 Sept
NZ$595
20 Sept - 21 Sept
includes taxes & fees
7.4/10 Good! (1,001 reviews)
Nice place by Bahia Honda and very close to Keys
"Overall the stay was nice. Good space. Clean. Manager was nice. Pool was clean. Very good rock band that plays at night also country. Bar is standard and the food offered was ok but that’s because they were still fixing something’s and the pizza was good. The only issue I had was the front desk who ..."

Reviewed on 17 Jul. 2025

Looe Key Reef Resort
See all 608 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
Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

NZ$1,116
per traveller
Marathon Backcountry Fishing Charter
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

NZ$46
per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
See all activities in Summerland Key

Frequently asked questions

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