Seaside Vacations from $431

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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.
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $737, price is now $431 per person
$431
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,462 reviews)
Nice property with friendly staff!

Reviewed on Aug 27, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was $1,478, price is now $674 per person
$674
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,003 reviews)
I loved the beachfront access

Reviewed on Aug 27, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $881, price is now $508 per person
$508
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (393 reviews)
Beautiful hotel very near the beach and shops Tigress bar on the 7th floor was amazing Great happy hour and excellent service and staff

Reviewed on Aug 27, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,306, price is now $804 per person
$804
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,000 reviews)
Great hotel at great location , ill be back!

Reviewed on Aug 28, 2025

Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $852, price is now $535 per person
$535
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (83 reviews)
Staff was so accommodating. Loved staying in 104. I’ll be back!!

Reviewed on Aug 22, 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
$197 nightly
The price is $219 total per night from Sep 8 to Sep 9
$219 total
Sep 8 - Sep 9
Total with taxes and fees
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
$207 nightly
The price is $231 total per night from Sep 4 to Sep 5
$231 total
Sep 4 - Sep 5
Total with taxes and fees
8.8/10 Excellent! (1,411 reviews)
"Great hotel and facilities, late notice of a power cut annoying as lifts out of operation lugging suitcases up stairs and air con etc in rooms. Otherwise great stay"

Reviewed on Aug 27, 2025

Margaritaville Beach Resort Fort Myers
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
12600 University Dr, Fort Myers, FL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $119 total per night from Sep 7 to Sep 8
$119 total
Sep 7 - Sep 8
Total with taxes and fees
8.4/10 Very Good! (987 reviews)
"Safe and quiet place. Easy parking. Strongly recommend."

Reviewed on Aug 23, 2025

Hilton Garden Inn Ft Myers
See all 16,414 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 great live music and lively festivals.

Miromar Outlets

Things to do

Fort Myers Beach Sunset Excursion

Fort Myers Beach Sunset Excursion

$60
per adult
100% of travellers recommend
Fort Myers Beach Sunset Excursion
Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

$65
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

$59
per adult
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
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.