
Estero Island Vacations from $405
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.

Matanzas Inn Bayside Resort and Marina
Price was $899, price is now $405 per person
$405
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,013 reviews)
Door slamming under cottage in the morning can be an early wake up call lol
Reviewed on Nov 14, 2025

Hyatt Place Fort Myers/at The Forum
The Forum
Save 100% on your flight
Price was $806, price is now $428 per person
$428
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
16.4/10 Exceptional! (1,004 reviews)
The room was clean but it smells very musty like needed window to air it out.
Reviewed on Nov 14, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $1,121, price is now $602 per person
$602
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
18.4/10 Exceptional! (704 reviews)
The property was beautiful. The staff was friendly. The bed and pillows were amazing.
Reviewed on Nov 15, 2025

Home2 Suites by Hilton Fort Myers Airport
Save 100% on your flight
Price was $865, price is now $485 per person
$485
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
18/10 Exceptional! (398 reviews)
The hotel was very clean, cozy, and well-maintained, creating a comfortable and relaxing atmosphere from the moment I arrived. The staff was friendly and helpful, and the room had everything I needed for a pleasant stay. I especially appreciated how spacious and modern the suite felt. Overall, I would definitely stay here again and highly recommend it to anyone looking for a clean, comfortable, and welcoming place to stay.
Reviewed on Nov 2, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $2,449, price is now $1,386 per person
$1,386
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
18/10 Exceptional! (1,000 reviews)
We had a very nice stay here.....the place is going through some construction but didnt distract alot. Had dinner one night at hotel, try the Black Grouper, very tasty. Only issue is the pricing. $50 for two drinks is steep, not to mention charging $44 a day for valet.......this was a big turn off.
Reviewed on Nov 17, 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

Lynn Hall Memorial Park
Walk over the water on a long pier that’s popular day and night for the breeze and fishing.

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.

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
$65
per adult
100% of travellers recommend

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
$65
per adult
Estero Island Hotel Deals

Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
$204 nightly
The price is $228 total per night from Dec 14 to Dec 15
$228 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (1,641 reviews)
Very nice and clean resort!
Reviewed on Nov 17, 2025

Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $201 total per night from Nov 24 to Nov 25
$201 total
Nov 24 - Nov 25
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
Breakfast was great but not included with the room price The 29 drink credit we had to ask them about it as we didn’t receive it upon check in. But they gave us a rum barrell drink ticket snd domestic beer drink ticket and he tossed in a couple of xtras. We don’t care for the rum drinks. But overall ...
Reviewed on Nov 15, 2025

Pink Shell Beach Resort and Marina
275 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$265 nightly
The price is $296 total per night from Nov 20 to Nov 21
$296 total
Nov 20 - Nov 21
Total with taxes and fees
9.4/10 Exceptional! (1,159 reviews)
Chester was very personable and helpful. All the front desk people very knowledgeable and helpful. We arrived at 8 am and were upgraded to an available room after arriving from another hotel.
Reviewed on Nov 13, 2025
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.
Find the Best Estero Island Vacation Packages
More vacations you might like
Explore a world of travel with Expedia
- Hotels near South Island
- Hotels near Santini Marina Shopping Plaza
- Hotels near Castle Beach
- Hotels near Laguna Shores
- Hotels near Mid Island
- Hotels near Sterling Ave Beach
- Lovers Key Hotels
- Fort Myers Beach Hotels
- Hotels near Mound Key Archaeological State Park
- Oceanfront Hotels in Fort Myers Beach
- Lovers Key State Park Hotels
- Pet-friendly Hotels in Lovers Key State Park
- 4 Star Hotels in Lovers Key State Park
- RV Parks in Lovers Key State Park
- Hotels near Mound House
- Hotels near Bonita Beach Dog Park
- Hotels near Winklers
- Hotels near Matanzaz Pass Preserve
- Hotels near Bay Oaks Recreation Center
- Hotels near Estero Boulevard Beach
- Condo Rentals in Fort Myers Beach
- All-inclusive Resorts in Fort Myers Beach
- Hotels near Raptor Bay Golf Club
- Beach Hotels in Fort Myers Beach
- Adults Only Resorts & in Fort Myers Beach
- Cheap Hotels in Fort Myers Beach
- Pet-friendly Hotels in Fort Myers Beach
- Hilton Hotels in Fort Myers Beach
- Motels in Fort Myers Beach
- Cottages in Fort Myers Beach
- Hotels with smoking rooms in Fort Myers Beach
- Extended Stay Hotels in Fort Myers Beach
- Sunstream Hotels in Fort Myers Beach
- Historic Hotels in Fort Myers Beach
- Hotels with Bars in Fort Myers Beach
- RV Parks in Fort Myers Beach
- Family Hotels in Fort Myers Beach
- Hotel Wedding Venues Hotels in Fort Myers Beach
- Safari Tentalow in Fort Myers Beach
- Gay friendly Hotels in Fort Myers Beach
- Villas in Fort Myers Beach
- Luxury Hotels in Fort Myers Beach
- Golf Hotels in Fort Myers Beach
- Casino Hotels in Fort Myers Beach
- Hotels with Restaurants in Fort Myers Beach
- Resorts in Fort Myers Beach
- Hotels with Kitchenettes in Fort Myers Beach
- Town Houses in Fort Myers Beach
- Fishing Resorts & in Fort Myers Beach
- Vacation Homes in Fort Myers Beach
- Apartments in Fort Myers Beach
- Hotels with Free Breakfast in Fort Myers Beach
- 5 Star Hotels in Fort Myers Beach
- Hotels with a Pool in Fort Myers Beach
- Hotels with Hot Tubs in Fort Myers Beach
- Boutique Hotels in Fort Myers Beach
- Aparthotels in Fort Myers Beach
- Quiet Resorts & in Fort Myers Beach
- Cabin Rentals in Fort Myers Beach
- Hotels with Connecting Rooms in Fort Myers Beach
- B&B in Fort Myers Beach
- Waterpark Hotels in Fort Myers Beach
- 3 Star Hotels in Fort Myers Beach
- 4 Star Hotels in Fort Myers Beach
- Condo Resorts in Fort Myers Beach
- Hotels with Balconies in Fort Myers Beach
- Hotels with Free Parking in Fort Myers Beach
- Resorts & Hotels with Spas in Fort Myers Beach
- Car rentals near Lovers Key State Park
- Car rentals near Estero Boulevard Beach
- Car rentals near Fort Myers Beach
- Car rentals near Raptor Bay Golf Club
- Van Car Rentals in Fort Myers Beach
- Enterprise Rental Cars in Fort Myers Beach
- Alamo Rent A Car Rental Cars in Fort Myers Beach
- National Car Rental Rental Cars in Fort Myers Beach
- Budget Rental Cars in Fort Myers Beach
- Thrifty Car Rental Rental Cars in Fort Myers Beach
- Avis Rental Cars in Fort Myers Beach
- Firefly Rental Cars in Fort Myers Beach
- U-Save Rental Cars in Fort Myers Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




















