
Estero Island Vacations from $276
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The Latest Estero Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Embassy Suites by Hilton Fort Myers Estero
Save 100% on your flight
Price was $413, price is now $276 per person
$276
per person
Nov 10 - Nov 13
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,016 reviews)
great breakfast, bar tender extremely friendly & hospitable & sports knowledgeable for a young man
Reviewed on Sep 10, 2025

Inn on Fifth
Old Naples
Price was $1,920, price is now $932 per person
$932
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
They know how to make you feel special. The service was incredible; everyone is very, very friendly. The hotel is beautiful, very quiet, and centrally located just a few minutes from the beach. If you want a place to relax, this is the one. We will definitely be back.
Reviewed on Sep 8, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $2,472, price is now $1,572 per person
$1,572
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,009 reviews)
Staff was friendly, hotel had a lot of construction outside by pool and beach, wasn't told this when I specifically called before I booked it. Also, Expedia shows prices that says inclusive of fees and taxes, yet I was charged $55 per day for "resort fee" plus additional minimal state and occupancy fees.
Reviewed on Sep 9, 2025

THE Palmview AND Sandpiper Inns
Save 100% on your flight
Price was $956, price is now $627 per person
$627
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (185 reviews)
It was close to the beach, and bikes have been provided.
There is a mold smell in the room, and walls are very thin, you can hear next door neighbors coughing or talking.
Reviewed on Aug 19, 2025

Bellasera Resort
Old Naples
Save 100% on your flight
Price was $2,035, price is now $1,386 per person
$1,386
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (2,218 reviews)
Excellent all around. The property is right next to everything you want to enjoy in Naples. They also offer a shuttle service up to 3 miles. The customer service of the staff was excellent, made you feel at home with any of your needs. The rooms are cute and clean perfect for a great stay with great balcony options. The pool is perfect not too big and saltwater! The restaurant on site is delicious. Favorite hotel in Naples! Thank you for everything
Reviewed on Sep 2, 2025
Don't see what you're looking for?
See all available trips from Columbus to Estero Island
View all tripsDiscover the most popular places to visit in Estero Island

Bunche Beach
Find a relatively obscure beach in a popular area of sand, warm water and a fascinating variety of coastal life. You’ll be thankful for the uncrowded space.

Lynn Hall Memorial Park
4.5/5(786 reviews)
Walk over the water on a long pier that’s popular day and night for the breeze and fishing.

Castle Beach
Why not spend a lazy afternoon at Castle Beach during your trip to Fort Myers Beach?
What to do in Estero Island

Fort Myers Beach Sunset Excursion
$60
per adult
100% of travellers recommend

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

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
$59
per adult
Estero Island Hotel Deals

Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
$214 nightly
The price is $239 total per night from Sep 11 to Sep 12
$239 total
Sep 11 - Sep 12
Total with taxes and fees

Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
$115 nightly
The price is $129 total per night from Sep 16 to Sep 17
$129 total
Sep 16 - Sep 17
Total with taxes and fees

Pink Shell Beach Resort and Marina
275 Estero Blvd, Fort Myers Beach, FL
$241 nightly
The price is $269 total per night from Sep 24 to Sep 25
$269 total
Sep 24 - Sep 25
Total with taxes and fees
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.