Estero Island Vacation Packages 2026 from $867

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The Latest Estero Island vacation packages

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

Bellasera Resort

Old Naples

Save 100% on your flight

$867

per person

Nov 16 - Nov 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (2,335 reviews)

Excellent staff...everyone. Rooms were also great.

Reviewed on Oct 12, 2026

The Perry Hotel Naples

Save 100% on your flight

$1,065

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

Clean rooms, parking , top pool

Reviewed on Oct 16, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$2,406,971

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,003 reviews)

Manasota Key Resort

Save 100% on your flight

$1,648

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (333 reviews)

Windward Passage Resort

Save 100% on your flight

$1,058

per person

Nov 19 - Nov 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.4/10 Very Good! (19 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

$199 nightly

$222 total

Oct 18 - Oct 19

Total with taxes and fees

Lani Kai Beachfront Resort

1400 Estero Blvd Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$139 nightly

$155 total

Oct 18 - Oct 19

Total with taxes and fees

8.8/10 Excellent! (2,123 reviews)

"Everyone was so friendly and helpful and the rooms were very clean and well maintained."

Reviewed on Oct 16, 2026

The Lighthouse Resort Inn & Suites

1051 5th St Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$143 nightly

$160 total

Oct 21 - Oct 22

Total with taxes and fees

8.6/10 Excellent! (1,819 reviews)

"Room was available early. Upgraded with nice view of pool and parking close by. Bath towels double as pool towel but there were enough and room is refreshed everyday. Mattress was very firm. Like that they had rugs on both sides of bed to collect grime. Shower took awhile to warm up and leaked all ..."

Reviewed on Oct 16, 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.