Southside Village Vacation Packages

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Top Holiday Package Deals in Southside Village

Price found within the past 48 hours. Click for updated prices.

Innisbrook Resort

CA $850

per person

Oct 25 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

8.4/10 Very good! (1,001 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $1,242

per person

Nov 1 - Nov 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (1,128 reviews)

Everything was good

Reviewed on Aug 17, 2026

CW Hotel

CA $1,188

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (48 reviews)

It’s a vibe and the view was amazing. House keeping very friendly.

Reviewed on Aug 17, 2026

The Avalon Club

CA $2,001

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (581 reviews)

Great place ,one step away from the beach ,free coffee all day ,free chairs umbrellas and towels also kids toys ,we really enjoyed the stay

Reviewed on Aug 15, 2026

The Westin Sarasota

Central Sarasota

CA $1,285

per person

Oct 20 - Oct 25

found 8 hours ago

Roundtrip flight included

Hamilton (YHM) to Tampa (TPA)

9/10 Wonderful! (1,151 reviews)

Where to stay in Southside Village

Find the best Southside Village areas and neighborhoods for the activities you enjoy most. Learn more about Southside Village

A sandy beach path with people walking, a wooden fence, and a clear blue sky with clouds.

Lido Key

Traverse a winding woodland path and spend the afternoon on this island’s secluded beaches before ending at a beachside bar to enjoy a spectacular sunset.

A cityscape with a mix of modern and historic buildings, palm trees, and a cloudy sky.

South Sarasota

Though South Sarasota might not have many top sights, you can venture to the surrounding area to see attractions like Siesta Key Beach and The Landings.

A waterfront with palm trees, a dock, and a clear blue sky.

Central Sarasota

2 out of top 10 points of interest in this area

Gardens, art galleries, and theaters are some highlights of Central Sarasota. Make a stop by Sarasota Opera House or Marina Jack while you're exploring.

A beach with clear water, rocks, and a sunset.

Palmer Ranch

When in Palmer Ranch, you can plan a visit to Stoneybrook Golf & Country Club and Sarasota Square, some noteworthy sights in the nearby area.

A wooden pier extending into a body of water with a cloudy sky above.

Downtown Sarasota

If you're spending some time in Downtown Sarasota, Sarasota Opera House and Regal Hollywood - Sarasota are top sights worth seeing.

Southside Village Hotel Deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Fully refundableReserve now, pay when you stay

CA $55

CA $91 total

Aug 25 - Aug 26

includes taxes & fees

9.2/10 Wonderful! (5,864 reviews)

"Excellent stay in Sarasota. A beautiful hotel with friendly staff :)"

Reviewed on Aug 17, 2026

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Fully refundableReserve now, pay when you stay

CA $210

CA $277 total

Sep 1 - Sep 2

includes taxes & fees

9.4/10 Exceptional! (2,477 reviews)

"Elissa was great at the check in"

Reviewed on Aug 17, 2026

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

CA $188

CA $248 total

Sep 10 - Sep 11

includes taxes & fees

See all 14,200 properties in Southside Village

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.