Seaside Vacations from $536

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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.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $982, price is now $536 per person
$536
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Staff was friendly and helpful! The location is convenient to restaurants and shops. On site restaurant was a great benefit.

Reviewed on Dec 6, 2025

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $1,305, price is now $723 per person
$723
per person
Feb 27 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Staff was fantastic. Room was nice and overall great experience.

Reviewed on Dec 7, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,476, price is now $824 per person
$824
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
We especially loved the kayaking

Reviewed on Dec 7, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $2,582, price is now $1,443 per person
$1,443
per person
Feb 27 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
Room was amazing! View spectacular! Service the best!

Reviewed on Dec 7, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,557, price is now $945 per person
$945
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
Nice, spacious rooms. Good bar and restaurant. Great gym. Also, no children!

Reviewed on Dec 4, 2025

Where to stay in Seaside

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

Find hotels in Stoneybrook

Seaside Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive Naples FL
Fully refundable
$401 nightly
The price is $446 total per night from Dec 21 to Dec 22
$446 total
Dec 21 - Dec 22
Total with taxes and fees
9/10 Wonderful! (1,962 reviews)
Great location

Reviewed on Dec 7, 2025

Naples Grande Beach Resort
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
$212 nightly
The price is $237 total per night from Dec 14 to Dec 15
$237 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (1,685 reviews)
Great place. Great entertainment

Reviewed on Dec 2, 2025

Margaritaville Beach Resort Fort Myers
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $172 total per night from Dec 9 to Dec 10
$172 total
Dec 9 - Dec 10
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Clean rooms, friendly staff, so much to do there and nearby

Reviewed on Dec 3, 2025

Lani Kai Beachfront Resort
See all 17,264 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Seaside

Hertz Arena showing landscape views

Hertz Arena

Palm trees may be swaying in the breeze, but inside people are gliding on ice. Select an activity from a roster of things to do at this popular venue.

Hertz Arena

Coconut Point Mall

You can search for that perfect souvenir at Coconut Point Mall during your stay in Estero. Wander the beautiful beaches or discover the area's beautiful sunsets.

Coconut Point Mall

Miromar Outlets

You can search for that perfect souvenir at Miromar Outlets during your stay in Estero. Experience the area's lively festivals and great live music.

Miromar Outlets

Things to do

Fort Myers Beach Sunset Excursion

Fort Myers Beach Sunset Excursion

$65
per adult
100% of travellers recommend
Fort Myers Beach Sunset Excursion
Copacetic Day Sail

Copacetic Day Sail

$70
per adult
100% of travellers recommend
Copacetic Day Sail
Cute Manatee

Manatee Sightseeing and Wildlife Boat Tour

$70
per adult
90% of travellers recommend
Manatee Sightseeing and Wildlife Boat Tour
See all activities in Estero
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.