Summerland Key Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Summerland Key

Price found within the past 48 hours. Click for updated prices.
Hilton Cabana Miami Beach Resort

Hilton Cabana Miami Beach Resort

4 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 13 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (292 reviews)
The hotel has potential, but cleanliness definitely needs improvement. Our bathroom had hair stuck to the ceiling of the shower and visible mold in some areas, which was off-putting. Additionally, the parking fees are excessive. Hilton charged $57 + tax for parking, while a lot just two minutes away on foot offered the same service for only $30. For guests already paying a premium to stay here, the parking costs feel unjustified. I’d strongly recommend lowering the price to be more competitive with the surrounding area.

Reviewed on 30 Jul 2025

The Gabriel Miami South Beach, Curio Collection by Hilton

The Gabriel Miami South Beach, Curio Collection by Hilton

4 out of 5
South Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 13 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (877 reviews)
The property had just gone under new management, and things were a bit hectic. Unfortunately, we didn’t have TV service during our entire stay. However, the manager, Eric, went above and beyond to make up for the inconvenience—providing $15 food vouchers throughout our visit and waiving the resort fees. What a fantastic way to turn things around and keep a guest happy! Superb team and a perfect location. Be sure to go see Eric and his staff—they’re truly amazing individuals!

Reviewed on 31 Jul 2025

Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flight
per person
24 Oct - 28 Oct
found 13 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,786 reviews)
Quiet ,clean property. Nice stay

Reviewed on 31 Jul 2025

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 13 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,099 reviews)
Everything was good however same breakfast choices everyday.

Reviewed on 20 Jul 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 13 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
Great property, location, eats, drinks, very attentive staff. A++

Reviewed on 31 Jul 2025

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

Top hotels in Summerland Key

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 €147 per night from 26 Aug to 27 Aug
€147
26 Aug - 27 Aug
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Loved the property and all of the free activities! We definitely took advantage of the kayaks, paddle boards, pool and hammocks."

Reviewed on 30 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! (420 reviews)
"We stayed for July 4th and it was perfect! Loved the suite and as a family it was very convenient to have a kitchen, washer and dryer!"

Reviewed on 29 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 €98 per night from 10 Aug to 11 Aug
€98
10 Aug - 11 Aug
includes taxes & fees
8/10 Very Good! (998 reviews)
"It was great"

Reviewed on 27 Jul 2025

Sugar Loaf Lodge
See all 606 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

Aboard the trolley in Key West

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

€48
per adult
86% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
12 hours Day at Key West With Boat Tour and Snorkeling

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

€24
per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Key West Haunted Tour : Ghosts & Gravestones

Key West Haunted Tour : Ghosts & Gravestones

€34
per adult
86% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
See all activities in Summerland Key

Frequently asked questions

How much does a Summerland Key holiday package cost?
You'll find cheap prices from €354 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.