Beachside Vacations from $1,275

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The Latest Beachside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

Old Town Key West
$1,275
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Had a very pleasant and great stay. The guy over the bar counter was super helpful and very professional. We will come back again.

Reviewed on Oct 16, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$2,946
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (563 reviews)
Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on Oct 6, 2026

Coconut Beach Resort

Coconut Beach Resort

Old Town Key West
Save 100% on your flight
$1,388
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (226 reviews)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
Save 100% on your flight
$1,463
per person
Jan 8 - Jan 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
.

Reviewed on Oct 17, 2026

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West
$5,374
per person
Dec 29 - Jan 3
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Where to stay in Beachside

Find the best Beachside areas and neighborhoods for the activities you enjoy most. Learn more about Beachside
A white building with shutters, palm trees, and a lawn.

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.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

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.

A two-story house with green shutters and a wooden balcony.

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.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

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 Fort East Martello Museum and Gallery.

A sunset over the ocean with scattered clouds.

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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$265 nightly
$298 total
Oct 19 - Oct 20
Total with taxes and fees
Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$175 nightly
$197 total
Oct 25 - Oct 26
Total with taxes and fees
Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$202 nightly
$227 total
Oct 27 - Oct 28
Total with taxes and fees
Beachside Resort & Residences
See all 2,779 properties in Beachside
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.
See properties

Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

$59
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.