Beachside Vacations from $403
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The Latest Beachside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
Save 100% on your flight
Price was $636, price is now $403 per person
$403
per person
Nov 10 - Nov 13
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.4/10 Very Good! (314 reviews)
Great hotel with excellent location
Reviewed on Sep 9, 2025
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,850, price is now $968 per person
$968
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (791 reviews)
Second mother / daughter trip to Key West - first time staying at Lighthouse Hotel. We loved it! The hotel is charming and the location is perfect. The staff was super friendly and answered all of our questions. Pool area and bar is great and we enjoyed a nice breakfast every morning before venturing out for the day. We rented bikes to get around and this location was ideal - easy ride to everywhere we wanted to go. We had a great stay and will definitely book this hotel again!
Reviewed on Sep 22, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,746, price is now $1,499 per person
$1,499
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
$30 a day for onsite parking is extortionate. It added 15% to my bill. To make things transparent, this should be more prominent in the pricing. This would stop me from returning. There are plenty of similar accommodations with free parking.
Reviewed on Oct 1, 2025
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,055, price is now $667 per person
$667
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,016 reviews)
This property was accommodating, staff friendly, courteous, clean, and concierge was extremely helpful. Will visit again soon.
Reviewed on Sep 26, 2025
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,953, price is now $1,235 per person
$1,235
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
Very good for visiting
Reviewed on Sep 27, 2025
Where to stay in Beachside
Find the best Beachside areas and neighborhoods for the activities you enjoy most. Learn more about Beachside
Old Town Key West
3 out of top 10 points of interest in this area
4.5/5(226 area reviews)
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
Beachside Hotel Deals
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $264 total per night from Oct 16 to Oct 17
$264 total
Oct 16 - Oct 17
Total with taxes and fees
8.6/10 Excellent! (1,790 reviews)
"We went during off peak season and it was amazing and quiet, relaxing."
Reviewed on Sep 23, 2025
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$197 nightly
The price is $222 total per night from Oct 12 to Oct 13
$222 total
Oct 12 - Oct 13
Total with taxes and fees
8.8/10 Excellent! (1,738 reviews)
"Very good for visiting"
Reviewed on Sep 27, 2025
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$229 nightly
The price is $258 total per night from Oct 29 to Oct 30
$258 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (2,788 reviews)
"Great"
Reviewed on Sep 28, 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.
Discover the most popular places to visit in Beachside
Smathers Beach
4/5(1,151 reviews)
Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$50
per adult
92% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
$80
per adult
92% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
$27
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.