Beachside Vacations from $1,418
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The Latest Beachside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,127, price is now $1,418 per person
$1,418
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
The staff that cleaned our room were great! Kept everything fresh and clean for our entire stay!
Reviewed on Jan 12, 2026
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,859, price is now $2,311 per person
$2,311
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.
Reviewed on Dec 12, 2025
The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $2,067, price is now $1,430 per person
$1,430
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
All staff were wonderful, especially the concierge. I also loved the ease of using the shuttle to get to the Old town. Everything was clean and comfortable. The room was actually spacious as well.
Reviewed on Jan 13, 2026
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $2,853, price is now $1,974 per person
$1,974
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,006 reviews)
I booked balcony view and we got the view of the back end of the cafe/bar . Listened to their hvac system while outside and the obnoxiously loud fountain that at night would gush water. Then on top of this was the ants in the room. They were all over the coffee area . Getting in our food . Had to throw away food. Also in the bathroom had ants fall down into my underwear. They said they were sending house keeping but if they came this needed more intervention. Hate to say this our room was nice. The air conditioner comes on every 15 minutes right above your head so another bad point. At $950 a night for the weekend. It makes me ill.
Reviewed on Jan 11, 2026
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $2,049, price is now $1,455 per person
$1,455
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
We were totally satisfied with our stay … being an Expedia VIP gave us extras we were not expecting !! Would recommend to others as we already have and they booked their stay in February
Reviewed on Jan 13, 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
5 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
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$327 nightly
The price is $368 total per night from Jan 14 to Jan 15
$368 total
Jan 14 - Jan 15
Total with taxes and fees
8.6/10 Excellent! (1,894 reviews)
Beautiful property, helpful staff , would highly recommend
Reviewed on Jan 11, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $329 total per night from Jan 14 to Jan 15
$329 total
Jan 14 - Jan 15
Total with taxes and fees
8/10 Very Good! (1,846 reviews)
Everything was clean, people were friendly. A lot to do there
Reviewed on Jan 11, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
$520 nightly
The price is $585 total per night from Jan 14 to Jan 15
$585 total
Jan 14 - Jan 15
Total with taxes and fees
8.6/10 Excellent! (3,008 reviews)
Room smelled musty all the time we were there and we ran the ac all the time. Also, breakfast was not served at guesthouse so we had to walk to main building every day. Not a big deal but it was not what we were told when we booked our stay. Otherwise, it was a very pleasant stay, all in all
Reviewed on Jan 12, 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.
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
Shipwreck Treasure Museum Tickets
$19
per adult
78% of travellers recommend
Sunset Sail in Key West with Beverages Included
$79
per adult
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.