Summerland Key Vacation Packages

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Your Summerland Key Vacation

The hassle-free way to experience this interesting city is with a tailor-made Summerland Key vacation package. Base yourself in the neighborhood of Sugarloaf Shores, which is great for families, fishing and views or go someplace else — our package deals are all about you. Cook Island, Big Pine Key Flea Market and Blue Hole are just some of the sights you'll want to see during your trip to Summerland Key. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Summerland Key vacation plans in motion!

Top Summerland Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Lazy river was great along with the pool and great beach access. GG the lady server that brings you food and drinks at the pool was one of the nicest and kindest people I’ve ever met at a hotel. She truly deserves a big raise. If GG isn’t making a little less than the manager then the management doesn’t know how to manage. GG literally went out of her way to try to make your pool day unforgettable. The only place I would ever be staying at when I return to Fort Lauderdale would be Pelican and reason being is the staff.

Reviewed on Jul. 12, 2025

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
Save 100% on your flight
per person
Sep 17 - Sep 23
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.6/10 Exceptional! (4 reviews)
Wonderful hotel. Beautiful design and very attentive staff.

Reviewed on Jul. 7, 2025

Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Save 100% on your flight
per person
Oct 1 - Oct 8
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9/10 Wonderful! (128 reviews)
i like the the hotel is apartments style with a full kitchen,washer and dryer.

Reviewed on Jul. 10, 2025

Pier Sixty-Six

Pier Sixty-Six

5 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Sep 17 - Sep 23
found 14 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.4/10 Exceptional! (76 reviews)
Stellar customer service.

Reviewed on Jul. 8, 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Save 100% on your flight
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9/10 Wonderful! (63 reviews)
No me gustó el sector ya que hay mucho ruido en la calle motos carros acelerando No deja dormir La habitación me gustó bastante pero no logré Disfrutarla

Reviewed on May 23, 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
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Cutthroat Harbor Estates

While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Venture Key are some notable places to visit nearby.

Find hotels in Cutthroat Harbor Estates

Ready to book your vacation to Summerland Key?

 

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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 CA $173 per night from Aug 10 to Aug 11
CA $173
CA $240 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,004 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 Jul. 9, 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 CA $136 per night from Aug 10 to Aug 11
CA $136
CA $153 total
Aug 10 - Aug 11
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 Jul. 6, 2025

Sugar Loaf Lodge
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 Jul. 7, 2025

Get rates
Sugarloaf Key Hotel at KOA Resort
See all 598 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

What to do in Summerland Key

A fun-filled adventure for the whole family

Guided Clear Kayak Eco-Tour Near Key West

CA $108
per adult
Guided Clear Kayak Eco-Tour Near Key West
Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

CA $911
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

CA $38
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 vacation package cost?
Offering great value package deals from CA $761 on Expedia, you'll be pleasantly surprised at how much a vacation to Summerland Key costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Summerland Key?
If you're looking to book a cheap Summerland Key vacation package, consider travelling in September, October and November. You'll typically find better rates on hotels and airfares during these months --- ideal for a budget-friendly break.
How many days is enough for Summerland Key?
We'd suggest booking a Summerland Key vacation for a minimum of 4 days. This gives you plenty of time to tick off top attractions including Blue Hole and Cook Island, and also explore neighbourhoods like Eden Pines and Cutthroat Harbour Estates. You could even squeeze in a day trip (or two) from Summerland Key.
How to find the best Summerland Key package deals?
Use Expedia's filter tool to find some terrific Summerland Key package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Summerland Key package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Summerland Key vacation as a package?
You can enjoy significant savings on your Summerland Key retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Summerland Key?
If you're considering an impromptu Summerland Key getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Summerland Key?

  1. Pick your dates: The things you plan to do in Summerland Key and your preferred season can help you decide when to get away.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will likely be the largest expense during your trip to Summerland Key.
  3. Decide how long to go for: Now that you know more about Summerland Key, you can work out the perfect length of your vacation. Create a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Summerland Key vacation package that brings all your bookings together.

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