
Beachside Vacations from $757
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The Latest Beachside Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,360, price is now $757 per person
$757
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Beautiful rooms and friendly staff!
Reviewed on Nov 26, 2025

Kona Kai Oasis
Old Town Key West
Price was $2,275, price is now $1,022 per person
$1,022
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.2/10 Very Good! (580 reviews)
It’s soo beautiful place to stay and everything is nearby
Reviewed on Nov 18, 2025

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,631, price is now $842 per person
$842
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
The front desk General Mgr upgraded us from an oceanview King Standard to an Oceanview King Suite, but the view of the ocean was more of a view of huge container tanks. We were told that the move will take place at 1-2p, unfortunately, the upgraded room promised was not ready until 4pm, so we moved to an alternate room because we were already packed and didn't want to waste our day.
On another day, we were told by dining staff to rush in 3 minutes because breakfast ends at 11a; however, 2 days later, we entered the dining room at 11:20a, and 2 dining servers told us that we could not be served lunch yet. We waited until 11:45a for a server to take our order. It was very strange!
The water pressure in our bathroom was poor and the carpet and shower tiles were soiled in the upgraded room compared to the original room. The elevator closest to our room was out of service even after 4 days.
18% gratuity is automatically included at their restaurant.
Pluses: the resort is nice and relaxing with an accommodating friendly staff.
The cushions in the pool areas were soiled.
Yellowfin is the only restaurant with delicious food and nice views.
Reviewed on Nov 29, 2025


Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,393, price is now $772 per person
$772
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Pool was great. Flat volleyballs. No cleaning service for 5d/4nights seemed strange when you pay an extra $220 for a resort fee.
Reviewed on Nov 28, 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
4 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

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
Key West FL
9.8/10 Exceptional! (33 reviews)
The location was awesome and the property manager was wonderful.
Reviewed on Sep 30, 2025

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $211 total per night from Dec 2 to Dec 3
$211 total
Dec 2 - Dec 3
Total with taxes and fees
8.6/10 Excellent! (1,720 reviews)
Great room, restaurant, and shuttle!
Reviewed on Nov 26, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $164 total per night from Nov 30 to Dec 1
$164 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (1,730 reviews)
Everything was beautiful and it was a pleasure to stay there. Will stay again.
Reviewed on Nov 25, 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
Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.
Things to do

Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend

Shipwreck Treasure Museum Tickets
$19
per adult
76% 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.























