Summerland Key Vacations from $290
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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!
The Latest Summerland Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
President Villa
South Beach
Save 100% on your flight
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,002 reviews)
Overall the hotel stay was good. However, you are paying more for the area you are in than the hotel itself. Morning breakfast was ok. That is a nice perk. However, if you're hoping to have your room cleaned everyday, you must ask for it. It won't get done otherwise. We didn't like having to go down daily to grab extra towels, toilet paper and shower amenities.
Also, robes and slippers should be supplied for every room as well as an extra blanket. And a must is a coffee maker! Please have that in your hotel rooms. We stayed in the President Villa. The room was a great size and balcony was amazing. But the lack of some amenities was disappointing.
Reviewed on Apr 28, 2025
Broadmore Miami Beach
North Beach
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.4/10 (227 reviews)
The hotel is definitely outdated but i love the nostalgia.Elevator was super slow but atleast it worked..My balcony room was excellent and better than expected. The smell all around each floors was so fresh. Richie was so patient and amazing and Panela was my savior and went over and beyond to accommodate to my needs and very pleasant.Housekeeping turn over was awful and had to still go to desk to get my missing items..I am definitely coming back..Thanks guys for a wonderful vacation!
Reviewed on Apr 24, 2025
May-Dee Suites
Hollywood Hills
Save 100% on your flight
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,349 reviews)
This is a hidden jewel among the many overrated and over priced hotels/motels nearby. It was very clean and the staff are remarkable.
Reviewed on Apr 28, 2025
Eden Roc Miami Beach
Mid Beach
Save 100% on your flight
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (2,387 reviews)
Loved my stay (which I extended) at Eden Roc. I was fortunate to have the most amazing view, and I did not want to leave. Candidly, I also needed to stay another night as the late checkout policy was not great... All the staff were very friendly. I was busy at an event so I did not take advantage of any of the amenities. I had a slight issue with the furniture/lighting in my room. And am happy I booked with Expedia at a discounted rate but overall much enjoyed.
Reviewed on Apr 30, 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
Cutthroat Harbor Estates
While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby.
Find the Best Summerland Key Vacation Packages
Summerland Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Max Temp Winter | 75ºF |
Max Temp Summer | 85ºF |
Top Sights | Bahia Honda State Park, Florida Keys Beaches and Calusa Beach |
Summerland Key Hotel Deals
Parmer's Resort
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is $234 per night from May 14 to May 15
$234
includes taxes & fees
$208 per night
May 14 - May 15
8.8/10 Excellent! (1,003 reviews)
"Very nice spot. Was clean and reasonably priced"
Reviewed on Apr 24, 2025
Looe Key Reef Resort
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is $168 per night from Jun 1 to Jun 2
$168
includes taxes & fees
$149 per night
Jun 1 - Jun 2
7.4/10 Good! (1,000 reviews)
"This little gem is great! Easy access right off U.S. 1. They have a large tiki bar with a food truck on site. There are a few other dining options within walking distance, but that's about it."
Reviewed on Apr 28, 2025
Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is $179 per night from May 4 to May 5
$179
includes taxes & fees
$159 per night
May 4 - May 5
8/10 Very Good! (998 reviews)
"Very peaceful, older property but extremely clean. Unassuming and quaint, Perfect for the price, can’t wait to go back"
Reviewed on Apr 20, 2025
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.
Frequently asked questions
Discover the most popular places to visit in Summerland Key
Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Upper Sugarloaf Key
4/5(21 reviews)
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
What to do in Summerland Key
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
$49
per adult
78% of travellers recommend
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Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.