Summerland Key Vacations from $494
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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.
Broadmore Miami Beach
North Beach
Price was $1,079, price is now $494 per person
$494
per person
Mar 17 - Mar 24
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.6/10 (389 reviews)
Location! Location! Location! Perfect. The lobby was nice. Check-in/ check-out was smooth. I will say that the room needed a LOT of TLC and the towels gave sandpaper serious competition. I was on the 2nd floor so the elevator wasn't an issue for us oer se ... HOWEVER it was super slow; definitely something to consider if you stay there on a higher floor. The fact that they only perform room service every 3 days could be an issue for some.
Reviewed on Dec 27, 2025
Bay Breeze Premium Apartments By Eskape Collection
Price was $1,540, price is now $662 per person
$662
per person
Mar 17 - Mar 24
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
Our two bedroom apartment was very comfortable and quiet. We enjoyed our stay very much.
Reviewed on Dec 30, 2025
Solé Miami, A Noble House Resort
Ocean Four
Price was $1,358, price is now $607 per person
$607
per person
Feb 7 - Feb 12
found 11 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,935 reviews)
The room was decent overall, though the bathrooms would benefit from an overhaul and closer attention to cleanliness. Elevator wait times were lengthy, and the front desk experience could be warmer and more welcoming. Additionally, the entrance and valet area lack curb appeal and would benefit from an aesthetic update to create a more inviting first impression.
Reviewed on Jan 6, 2026
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View all tripsWhere 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 Key and Venture Out Keys are some notable places to visit nearby.
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
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
What to do in Summerland Key
Summerland Key Hotel Deals
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $158 total per night from Jan 12 to Jan 13
$158 total
Jan 12 - Jan 13
Total with taxes and fees
7.4/10 Good! (1,005 reviews)
The management was new and friendly and helpful. The hotel needs a lot of updates. In our opinion, they need a better staff for housekeeping. The drinks at the bar were very reasonably priced. The location is great. Across the street, you can play miniature golf.
Reviewed on Dec 27, 2025
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
$258 nightly
The price is $290 total per night from Jan 11 to Jan 12
$290 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,016 reviews)
Excellent
Reviewed on Jan 5, 2026
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
$169 nightly
The price is $190 total per night from Jan 8 to Jan 9
$190 total
Jan 8 - Jan 9
Total with taxes and fees
8/10 Very Good! (1,005 reviews)
The room was spacious well proportioned very clean and friendly staff only drawback was no coffee pot in the room
Reviewed on Jan 1, 2026
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.
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 |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
