Search Deals on
Estero Island Vacation Packages

Build your package with 2 more options

Estero Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
GreenLinks Golf Villas at Lely Resort

GreenLinks Golf Villas at Lely Resort

3 out of 5
Price was $908, price is now $605 per person
$605
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3-star spa aparthotel in Naples. Enjoy free parking, a full-service spa, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions Flamingo Island Course - Lely Resort and Swamp Buggy Races are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $1,128, price is now $711 per person
$711
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4-star golf aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $1,393, price is now $896 per person
$896
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3-star 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 Times Square are located nearby.
Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,527, price is now $995 per person
$995
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 4-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Edison Beach House

Edison Beach House

3.5 out of 5
Price was $1,558, price is now $1,040 per person
$1,040
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Times Square are located nearby.
Inn on Fifth

Inn on Fifth

4 out of 5
Price was $2,308, price is now $1,575 per person
$1,575
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Save 100% on your flight
Price was $3,502, price is now $2,392 per person
$2,392
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 3.5-star beach condo in Fort Myers. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Key West Express and Sanibel Island Southern Beach are located nearby.
Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
Price was $2,195, price is now $1,536 per person
$1,536
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this 4-star beach resort in Marco Island. Enjoy a full-service spa, a beach locale, and room service. Our guests praise the pool and the restaurant in our reviews. Popular attractions Winterberry Beach and South Marco Beach are located nearby.

Estero Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $1,128, price is now $711 per person
$711
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $3,393, price is now $2,030 per person
$2,030
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,603, price is now $1,616 per person
$1,616
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $1,393, price is now $896 per person
$896
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)

Estero Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,279, price is now $634 per person
$634
per person
Dec 6 - Dec 13
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was $2,136, price is now $1,020 per person
$1,020
per person
Dec 6 - Dec 13
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $1,879, price is now $1,009 per person
$1,009
per person
Dec 29 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $2,338, price is now $1,315 per person
$1,315
per person
Dec 29 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Wed, Jan 21 - Wed, Jan 28
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Jan 21 from Portsmouth Intl. to Southwest Florida Intl., returning Wed, Jan 28, priced at $102 found 1 day ago
Spirit Airlines
Wed, Jan 14 - Wed, Jan 21
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$112 Roundtrip, found 23 hours ago
$112
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Wed, Jan 14 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Jan 21, priced at $112 found 23 hours ago
Spirit Airlines
Sun, Nov 9 - Wed, Nov 12
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Nov 9 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Wed, Nov 12, priced at $120 found 1 day ago
United
Tue, Nov 11 - Tue, Nov 18
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 1 hour ago
$127
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Nov 11 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Tue, Nov 18, priced at $127 found 1 hour ago