Search Deals onEstero Vacation Packages
Estero Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Olde Marco Island Inn and Suites
Save 100% on your flight
Price was $818, price is now $548 per person
$548
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Myers (RSW)
Stay at this hotel in Marco Island. Enjoy free WiFi, free parking, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions South Naples and Marco Island Beaches and Tigertail Beach are located nearby.
The Perry Hotel Naples
Save 100% on your flight
Price was $1,414, price is now $810 per person
$810
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Delnor-Wiggins Pass State Park are located nearby.
Clean room, nice fixtures, quietest room a/c I’ve ever experienced in a hotel
Boat ride to the beach was awesome
Reviewed on Aug 22, 2026
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,351, price is now $816 per person
$816
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy free parking, 2 outdoor pools, and a full-service spa. Popular attractions Bowman's Beach and Captiva Beach are located nearby.
Casa Ybel Resort
Save 100% on your flight
Price was $1,234, price is now $784 per person
$784
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Sanibel Island Southern Beach and Sanibel Island Lighthouse are located nearby.
Matanzas Inn Bayside Resort and Marina
Save 100% on your flight
Price was $1,117, price is now $712 per person
$712
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Ooooooooooooookeeeeeeeyyyyyyyyy
Reviewed on Aug 22, 2026
Casa Tiki
Save 100% on your flight
Price was $1,135, price is now $736 per person
$736
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this vacation home in Cape Coral. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Four Mile Cove Ecological Preserve and Coralwood Mall are located nearby.
Marriott Sanibel Harbour Resort & Spa
Save 100% on your flight
Price was $1,555, price is now $1,025 per person
$1,025
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Key West Express and Sanibel Island Lighthouse are located nearby.
The check in process was quick and were given 2 welcome drink passes for the bar which was great. The problem was the elevators which only 2 were operational and took anywhere from 3-9min just to go floor by floor at any given moment.the restaurants were a bit expensive but still gaave it a try. The spa is definitely recommended as well as the gym which is very stocked. The pools was nice and never crowded. The bimini restaurant which is a small golf cart drive away is very recommended. The height of the stay were the amazing sunsets by the poolside which were incredible. Overall the stay was good, but try it out . Enjoy!
Reviewed on Aug 21, 2026
Windward Passage Resort
Save 100% on your flight
Price was $1,144, price is now $781 per person
$781
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Estero Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Estero Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sun, Nov 15 - Sat, Dec 5
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$166 Roundtrip, found 7 hours ago
$166
Roundtrip
found 7 hours ago
Wed, Jan 13 - Sat, Jan 16
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$173 Roundtrip, found 3 hours ago
$173
Roundtrip
found 3 hours ago
Sun, Jan 24 - Mon, Feb 1
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$207 Roundtrip, found 21 hours ago
$207
Roundtrip
found 21 hours ago
Sun, Nov 15 - Thu, Nov 19
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
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