Search Deals on
Estero Vacation Packages

Build your package with 2 more options

Estero Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $985, price is now $661 per person
$661
per person
Jun 19 - Jun 24
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.
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Save 100% on your flight
Price was $1,570, price is now $867 per person
$867
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this luxury resort in Naples. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach 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 $1,509, price is now $939 per person
$939
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this golf hotel 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.
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
Save 100% on your flight
Price was $1,600, price is now $1,006 per person
$1,006
per person
May 19 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach condo 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.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,410, price is now $931 per person
$931
per person
May 19 - May 26
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 Barefoot Beach are located nearby.
Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,528, price is now $1,009 per person
$1,009
per person
May 19 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach resort 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.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,818, price is now $1,211 per person
$1,211
per person
May 19 - May 26
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 Captiva Beach and Captiva Chapel By the Sea are located nearby.
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $1,060, price is now $714 per person
$714
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this 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 Estero Boulevard Beach are located nearby.

Estero Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was $778, price is now $542 per person
$542
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $926, price is now $612 per person
$612
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
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 $917, price is now $629 per person
$629
per person
Jul 13 - Jul 16
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was $875, price is now $610 per person
$610
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Estero 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 $985, price is now $627 per person
$627
per person
Jul 12 - Jul 17
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,570, price is now $867 per person
$867
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
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 $1,509, price is now $939 per person
$939
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
South Island
Save 100% on your flight
Price was $1,600, price is now $1,006 per person
$1,006
per person
May 19 - May 26
found 1 day ago
Roundtrip 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.

Spirit Airlines
Sun, Apr 26 - Thu, Apr 30
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$90 Roundtrip, found 3 hours ago
$90
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sun, Apr 26 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Apr 30, priced at $90 found 3 hours ago
Frontier Airlines
Sun, May 10 - Tue, May 19
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$101 Roundtrip, found 3 hours ago
$101
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, May 10 from Philadelphia Intl. to Southwest Florida Intl., returning Tue, May 19, priced at $101 found 3 hours ago
Frontier Airlines
Sun, May 3 - Wed, May 20
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$105 Roundtrip, found 3 hours ago
$105
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, May 3 from Hopkins Intl. to Southwest Florida Intl., returning Wed, May 20, priced at $105 found 3 hours ago
United
Sat, May 2 - Wed, May 13
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Select United flight, departing Sat, May 2 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Wed, May 13, priced at $197 found 15 hours ago