Estero Island Vacation Packages 2026 from $990

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The Latest Estero Island vacation packages

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

The Perry Hotel Naples

Save 100% on your flight

$990

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$5,150

per person

Dec 26 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

The was very clean. Every day. The staff very friendly . The beach awesome lady

Reviewed on Oct 13, 2026

Edison Beach House

Save 100% on your flight

$1,988

per person

Dec 25 - Jan 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (1,921 reviews)

Excellent

Reviewed on Oct 11, 2026

Landing Apartments Fort Myers near Eastwood Village

Save 100% on your flight

$1,048

per person

Dec 22 - Dec 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (31 reviews)

This place is as beautiful as the pictures. Welcome kit has essentials for a short stay. The place is clean and cozy. Highly recommended.

Reviewed on Sep 4, 2026

Southseas

Save 100% on your flight

$2,942

per person

Dec 26 - Jan 2

found 5 hours ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

No 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

Fully refundableReserve now, pay when you stay

$202 nightly

$226 total

Oct 27 - Oct 28

Total with taxes and fees

9/10 Wonderful! (2,666 reviews)

"Stay was prefect. Has everything you need."

Reviewed on Oct 13, 2026

Lani Kai Beachfront Resort

1400 Estero Blvd Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$165 nightly

$184 total

Oct 25 - Oct 26

Total with taxes and fees

8.8/10 Excellent! (2,113 reviews)

"Rooms were clean - View was amazing. Not the bet kitchen for cooking."

Reviewed on Oct 14, 2026

The Lighthouse Resort Inn & Suites

1051 5th St Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$147 nightly

$164 total

Oct 15 - Oct 16

Total with taxes and fees

8.6/10 Excellent! (1,818 reviews)

"This is a great place! We’ve stayed here several times! New pool is fabulous!"

Reviewed on Oct 14, 2026

See all 2,891 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.