Estero Island Vacation Packages 2026 from $504

Photo by Stephanie Karasek

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Estero Island vacation packages

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

The Lighthouse Resort Inn & Suites

Save 100% on your flight

$504

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,787 reviews)

We had a great time!

Reviewed on Sep 22, 2026

The Perry Hotel Naples

Save 100% on your flight

$972

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Great all around!

Reviewed on Sep 23, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Save 100% on your flight

$536

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (3,301 reviews)

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$532

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (1,006 reviews)

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$869

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (13 reviews)

Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Estero Island

View all trips

Stay near popular Estero Island attractions

Bowditch Point Park

8.6/10 (621 reviews)

You can take time to visit Bowditch Point Park during your travels to Fort Myers Beach. Amble around this family-friendly area's beautiful beaches and enjoy its lively bars.

See properties

Times Square

9.0/10 (18 reviews)

After visiting Times Square, make a plan to see the other sights and activities in Fort Myers Beach.

See properties

Santini Marina Shopping Plaza

8.8/10 (527 reviews)

You can browse for the perfect souvenirs at Santini Marina Shopping Plaza during your visit to Fort Myers Beach. Wander the beautiful beaches or discover the beautiful sunsets in this family-friendly area.

See properties

Mound House

7.8/10 (28 reviews)

Learn about the local history of Fort Myers Beach with a stop at Mound House. Wander the beautiful beaches and seaside in this family-friendly area.

See properties

Bay Oaks Recreation Center

8.0/10 (120 reviews)

After visiting Bay Oaks Recreation Center, make a plan to see the other sights and activities in Fort Myers Beach. Stroll along the seaside in this family-friendly area, or check out its top-notch restaurants.

See properties

What to do in Estero Island

Fort Myers Beach Sunset and Dolphin Watching Cruise

$63

per adult

100% of travellers recommend

2.5-Hour Guided Group Kayak Tour on Big Hickory Pass

$55

per adult

Copacetic Day Sail

$70

per adult

100% of travellers recommend

See all activities in Estero Island

Estero Island Hotel Deals

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$195 nightly

$218 total

Oct 1 - Oct 2

Total with taxes and fees

9/10 Wonderful! (2,580 reviews)

"We had to request a room change. Not sure what was going on this weekend, but teenagers being loud, running up and down the halls, sitting on the floors of the hallways, and being loud in the rooms til past midnight. First time I have ever called security to keep the noise down. We were moved across ..."

Reviewed on Sep 22, 2026

Lani Kai Beachfront Resort

1400 Estero Blvd Fort Myers Beach FL

$119 nightly

$132 total

Sep 27 - Sep 28

Total with taxes and fees

Pink Shell Beach Resort and Marina

275 Estero Blvd Fort Myers Beach FL

$259 nightly

$288 total

Sep 30 - Oct 1

Total with taxes and fees

9.4/10 Exceptional! (1,445 reviews)

"It was our first visit since the last devastating hurricane. We were pleased how well the hotel looked and amenities and staff were great. Everyone was friendly and dining at Rae's was outstanding. We are local and will definitely be back"

Reviewed on Sep 23, 2026

See all 2,882 properties in Estero Island

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.