Seaside Vacations from $262

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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
Price was $679, price is now $262 per person
$262
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Very nice Staff is excellent.

Reviewed on Nov 24, 2025

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was $571, price is now $267 per person
$267
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
the place was nice but there was a cockroack in the bathroom.

Reviewed on Nov 20, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,169, price is now $602 per person
$602
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
The bed was very comfortable. The shower was clean and updated. We enjoyed the fire pits at night.

Reviewed on Nov 27, 2025

Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Save 100% on your flight
Price was $562, price is now $303 per person
$303
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.2/10 Very Good! (1,004 reviews)
Everything was fantastic as usual!

Reviewed on Nov 24, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,985, price is now $1,106 per person
$1,106
per person
Feb 16 - Feb 21
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
El personal súper amable y todo muy limpio,la habitación excelente

Reviewed on Nov 24, 2025

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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

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
$204 nightly
The price is $228 total per night from Dec 14 to Dec 15
$228 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (1,655 reviews)
This is a wonderful hotel, rooms are beautiful and amenities wonderful. We will definitely come back.

Reviewed on Nov 23, 2025

Margaritaville Beach Resort Fort Myers
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive Naples FL
Fully refundableReserve now, pay when you stay
$313 nightly
The price is $348 total per night from Dec 1 to Dec 2
$348 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (1,929 reviews)
THE STAFF AND ROOMS WERE GREAT. THE LOCATION IS CLOSE TO EVERYTHING AND ENJOYED THE FOOD AND DRINKS AT THE BAR EXCELLENT CHOICE OF BOURBONS

Reviewed on Nov 21, 2025

Naples Grande Beach Resort
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
$162 nightly
The price is $181 total per night from Nov 30 to Dec 1
$181 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,038 reviews)
Everything was perfect.

Reviewed on Nov 28, 2025

Lani Kai Beachfront Resort
See all 17,154 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.
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Discover the most popular places to visit in Seaside

Hertz Arena showing landscape views

Hertz Arena

4/5(161 reviews)

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

4.5/5(439 reviews)

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

4.5/5(326 reviews)

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
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

$70
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

$65
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
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.