Seaside Vacation Packages 2026 from $596

Your Seaside Vacation

Whatever your travel style, you can experience it all with a tailor-made Seaside vacation package. Spend your next getaway enjoying this neighborhood's golfing and its other charms. Your trip to Seaside wouldn't be complete without stopping by major attractions nearby such as Hertz Arena, Coconut Point Mall and Miromar Outlets. Whatever your travel plans or the size of your budget, booking your dream Seaside vacation is quick and easy with Expedia.

The Latest Seaside Vacation Packages

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

The Lighthouse Resort Inn & Suites

Save 100% on your flight

$596

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,781 reviews)

The Perry Hotel Naples

$1,306

per person

Nov 4 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,074 reviews)

!!!

Reviewed on Sep 2, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$806

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,011 reviews)

Resort Harbour Properties

Punta Rassa

Save 100% on your flight

$1,007

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (372 reviews)

The property was clean and absolutely gorgeous. The pictures honestly didn't do it justice. The hospitality was great! The communication was top notch, but they weren't too much at all. Great privacy! Beach was steps away from the elevator. The location was wonderful! It was secluded but everything we needed was very close by. Sanibel Island was a 10 minute drive at most! We are only going to stay at this property in the future.

Reviewed on Aug 11, 2026

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$820

per person

Oct 10 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (13 reviews)

Pleasant stay. Staff friendly and attentive. Very relaxing stay. The view of the beach is a plus.

Reviewed on Aug 5, 2026

Where to stay in Seaside

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

A river with a sandy beach, dense green vegetation, and a city skyline in the background.

Stoneybrook

1 out of top 10 points of interest in this area

Though Stoneybrook might not have many top sights, you can venture to the surrounding area to see attractions like Miromar Outlets and Stoneybrook Golf Club.

The Villages at Country Creek

The Villages at Country Creek might not have many top sights, but Hertz Arena and Miromar Outlets are two attractions nearby that you can check out.

A calm river with a green kayak on the shore, surrounded by trees and a distant city skyline.

Fountain Lakes

If you're looking for some top things to see and do in Fountain Lakes and surrounding area, you can visit Coconut Point Mall and Saltleaf Golf Preserve.

Riverwoods Plantation

Though Riverwoods Plantation might not have many top sights, you can venture to the surrounding area to see attractions like Koreshan State Park and Hertz Arena.

Corkscrew Woodlands

When in Corkscrew Woodlands, you can plan a visit to Miromar Outlets and Hertz Arena, some noteworthy sights in the nearby area.

Seaside Hotel Deals

Marriott Sanibel Harbour Resort & Spa

17260 Harbour Pointe Dr Fort Myers FL

Fully refundableReserve now, pay when you stay

$223 nightly

$248 total

Sep 16 - Sep 17

Total with taxes and fees

8.6/10 Excellent! (1,000 reviews)

"Great amenities, attentive staff, beautiful location, one of the best facilities in the SWFL area"

Reviewed on Sep 2, 2026

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$181 nightly

$202 total

Sep 9 - Sep 10

Total with taxes and fees

Baymont by Wyndham Fort Myers Central

4850 S Cleveland Ave Fort Myers FL

Fully refundableReserve now, pay when you stay

$66 nightly

$73 total

Sep 10 - Sep 11

Total with taxes and fees

6.8/10 (1,159 reviews)

"Room looked like it rented per hour and stunk of mold. Water stains on the ceiling and the bathroom needed about 3 gallons of bleach"

Reviewed on Sep 2, 2026

See all 17,772 properties in Seaside

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.