Estero Island Vacation Packages 2026 from $569

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The Latest Estero Island vacation packages

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

Olde Marco Island Inn and Suites

Olde Marco

Save 100% on your flight

$569

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,002 reviews)

The Perry Hotel Naples

Save 100% on your flight

$959

per person

Dec 11 - Dec 15

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,163 reviews)

Tween Waters Island Resort & Spa

Save 100% on your flight

$711

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

The Lighthouse Resort Inn & Suites

Save 100% on your flight

$918

per person

Nov 16 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,790 reviews)

We stayed in their new building which is very nice. Clean room. It had everything we

Reviewed on Sep 29, 2026

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight

$588

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (1,003 reviews)

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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.

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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.

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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.

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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.

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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.

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What to do in Estero Island

Fort Myers Beach Sunset and Dolphin Watching Cruise

$70

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

$194 nightly

$216 total

Oct 1 - Oct 2

Total with taxes and fees

Lani Kai Beachfront Resort

1400 Estero Blvd Fort Myers Beach FL

$133 nightly

$148 total

Oct 13 - Oct 14

Total with taxes and fees

8.8/10 Excellent! (2,071 reviews)

"Everything was great and staff was excellent. Easy access to everything! Good food bars!"

Reviewed on Sep 29, 2026

Pink Shell Beach Resort and Marina

275 Estero Blvd Fort Myers Beach FL

$264 nightly

$294 total

Oct 25 - Oct 26

Total with taxes and fees

9.4/10 Exceptional! (1,448 reviews)

"It was absolutely fantastic! We will be there next September and will be bringing more family with us. Please remember me if you have any special offers. The only thing that would have made it better is we were staying in the third building with the adult pool and we would love to have gone in and ..."

Reviewed on Sep 27, 2026

See all 2,879 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.