Beachside Vacations from $1,379
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The Latest Beachside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive
Old Town Key West
$1,379
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
We were on the top floor. Lots of stairs. Make sure you can do stairs when booking or request a lower floor. It's beautiful, great location and would go back again.
Reviewed on Sep 1, 2026
Ella's Cottages - Key West Historic Inns
Old Town Key West
$1,726
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (494 reviews)
It is located in the heart of he old district snd everything was so accessible without having to use our car. The property is only 1 block off Duval so,we had the advantage of,accessibility without the noise. The property is protected by foliage which makes it feel private and protected. The complimentary breakfast is lovely, and there is wine by the pool daily. Dwight welcomes guests upon arrival,and made us feel,at home. The beds are so comfy, and each cottage has its own flavor. I hope to return and stay at Ella’s Cottages again, Expedia does a great job helping us narrow down our priorities, amenities, location, etc. That enabled us to find Ella’s Cottages, which was perfect for us.
Reviewed on Sep 1, 2026
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
4 out of top 10 points of interest in this area
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.
Downtown Key West
If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.
Key West Historic District
2 out of top 10 points of interest in this area
Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.
New Town
Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Beachside Hotel Deals
Beachfront 2BDR Condo, Pool & Hot Tub w/ Ocean Views | Papaya Place by AvantStay
Key West FL
8.8/10 Excellent! (57 reviews)
"Clean, and communication with host was excellent."
Reviewed on Jan 14, 2026
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Key West FL
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$210 nightly
$237 total
Sep 8 - Sep 9
Total with taxes and fees
8.6/10 Excellent! (3,561 reviews)
"The resort fee is very expensive for what the resort has to offer for the guests. I will not rebook this resort the next time we are in Keywest. No shuttle services are offered. Nothing complimentary but two welcome drinks."
Reviewed on Sep 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.
Stay near popular Beachside attractions
Smathers Beach
8.4/10 (8,320 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
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
$69
per adult
88% of travellers recommend
Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.