A vibrant building with a purple facade, a sign reading "Siesta," and a staircase leading to the entrance.

Siesta Key Village Vacations from $649

Book a Hotel + Flight or Car together to unlock savings

Your Siesta Key Village Vacation

Uncovering everything Siesta Key Village has to offer is a breeze with a Siesta Key Village vacation package. Known for its coastal beaches and more, this intriguing neighborhood is calling your name. Hoping to sightsee during your trip to Siesta Key Village? Pencil in a visit to nearby attractions like Siesta Key Beach, Lido Beach and Crescent Beach. Stop daydreaming and start doing. When you're ready to lock in your ideal vacation to Siesta Key Village, Expedia will help get you there.

The Latest Siesta Key Village Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A modern interior with a wooden spiral staircase, a hallway leading to a bathroom, and a small blue console table.
    Jan 17 - Jan 23

    IRB Intercoastal + Flight

    Indian Shores
    6 nights
    3.0 star property
    Roundtrip • Philadelphia (PHL) - Tampa (TPA)
    PHL - TPA • Nonstop TPA - PHL • 1 stop
    $986
    $649
    per traveler
    found 1 day ago
    IRB Intercoastal
  • A modern kitchen with a large island, white cabinetry, and a view of the beach.
    Feb 5 - Feb 9

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    4 nights
    4.0 star property
    9.6/10 - Exceptional (1,328 reviews)
    "Loved the property will stay again"
    Reviewed November 11, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $1,714
    $1,047
    per traveler
    found 12 hours ago
    Ocean Club Treasure Island Hotel
  • A bedroom with a large bed, a nightstand, a chair, and a view of the ocean.
    Jan 28 - Feb 3

    Crystal Palms Beach Resort + Flight

    Sunshine Beach
    6 nights
    3.5 star property
    8.8/10 - Excellent (2,416 reviews)
    "It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $1,207
    $744
    per traveler
    found 17 hours ago
    Crystal Palms Beach Resort
  • A modern living room with a large window, a sofa set, a coffee table, and a dining area.
    Dec 27 - Jan 1

    CW Resort + Flight

    Clearwater Beach
    5 nights
    4.0 star property
    9.4/10 - Exceptional (311 reviews)
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • 1 stop
    $2,835
    $1,914
    per traveler
    found 1 day ago
    CW Resort
  • An outdoor patio with tables and chairs, palm trees, and a view of the water.
    Feb 5 - Feb 9

    Westwinds Waterfront Resort + Flight

    Treasure Island
    4 nights
    3.0 star property
    9.0/10 - Wonderful (748 reviews)
    "It was a great location for the beach, dinner, and awesome spot to just hang out on the property! Beautiful beautiful place!!"
    Reviewed November 9, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $1,208
    $821
    per traveler
    found 12 hours ago
    Westwinds Waterfront Resort

Where to stay in Siesta Key Village

Find the best Siesta Key Village areas and neighborhoods for the activities you enjoy most. Learn more about Siesta Key Village
Learn more about Siesta Key Village
A large, beige colonial-style building with columns, surrounded by palm trees and dense vegetation.
Photo by Michael Serrao
Open Photo by Michael Serrao

South Village

While visiting South Village, you might make a stop by sights like Safe Harbor Siesta Key and Crescent Beach.

Aloha Kai

While Aloha Kai isn't home to many top sights, Siesta Key Beach and Crescent Beach are some notable places to visit nearby.

Bailey Hall

When in Bailey Hall, you can plan a visit to Siesta Key Beach and Lido Beach, some noteworthy sights in the nearby area.

Point of Rocks

While there might not be top attractions in Point of Rocks, you can explore the larger area and discover places like Siesta Key Beach and Point of Rocks.

White Beach

When in White Beach, you can plan a visit to Point of Rocks and Safe Harbor Siesta Key, some noteworthy sights in the nearby area.

Discover the most popular places to visit in Siesta Key Village

Siesta Key Farmers Market

You can enjoy retail therapy at Siesta Key Farmers Market during your trip to Siesta Key. Amble around this quaint area's beautiful beaches and enjoy its lively bars.
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What to do near Siesta Key Village

Mangroves, Manatees & a Hidden Beach Kayak Tour (Siesta Key)

Mangrove Tunnel & Manatee Kayak Eco-Tour

$59
per adult
96% of travelers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
See all activities near Siesta Key Village

Siesta Key Village Hotel Deals

A stone pathway leading through a tropical garden with palm trees and a signboard.

Tropical Breeze Resort

Tropical Breeze Resort
3.0 star property
Siesta Key Village
8.8 out of 10, Excellent, (1,041 reviews)
$117 nightly
The price is $132
Dec 13 - Dec 14
Total with taxes and fees
Tropical Breeze Resort
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.
See all properties in Siesta Key Village
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.