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Estero Vacation Packages

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Estero Flight + Hotel Packages

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
Save 100% on your flight
Price was $527, price is now $317 per person
$317
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Great overall highly recommended

Reviewed on Jul 12, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $700, price is now $422 per person
$422
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Delnor-Wiggins Pass State Park and Vanderbilt Beach are located nearby.
CLEAN ROOM

Reviewed on Jul 10, 2026

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Save 100% on your flight
Price was $647, price is now $394 per person
$394
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Stay at this hotel in Punta Gorda. Popular attractions Fishermen's Village and Peace River are located nearby.
Spectacular property, I will recommend it to all my friends and family

Reviewed on Jul 11, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $897, price is now $559 per person
$559
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Bowman's Beach are located nearby.
Awesome

Reviewed on Jul 10, 2026

Inn on Fifth

Inn on Fifth

4 out of 5
Save 100% on your flight
Price was $1,138, price is now $753 per person
$753
per person
Oct 1 - Oct 5
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this 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 Beach are located nearby.
Wonderful experience.

Reviewed on Jul 11, 2026

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $794, price is now $529 per person
$529
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The property was well restored and maintained. Staff (at the pool) needs to level up.

Reviewed on Jul 10, 2026

Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $930, price is now $621 per person
$621
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this beach hotel in Englewood. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Englewood Beach and Manasota Beach are located nearby.
We LOVED our trip to Manasota Key. Staff was outstanding, room very clean, beach was awesome. Enjoyed every minute. We will be back.

Reviewed on Jul 10, 2026

Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
Price was $1,325, price is now $884 per person
$884
per person
Oct 1 - Oct 5
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly aparthotel in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby.
All in all it was excellent. The elevator to our third floor was smelly, could not pinpoint smell

Reviewed on Jul 5, 2026

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
Save 100% on your flight
Price was $527, price is now $317 per person
$317
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $700, price is now $422 per person
$422
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Save 100% on your flight
Price was $647, price is now $394 per person
$394
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $897, price is now $559 per person
$559
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $883, price is now $541 per person
$541
per person
Aug 29 - Sep 5
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 $1,512, price is now $803 per person
$803
per person
Sep 14 - Sep 19
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $1,331, price is now $858 per person
$858
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,306, price is now $864 per person
$864
per person
Aug 29 - Sep 5
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.

Frontier Airlines
Mon, Aug 17 - Sun, Sep 6
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$105 Roundtrip, found 8 hours ago
$105
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Mon, Aug 17 from Hopkins Intl. to Southwest Florida Intl., returning Sun, Sep 6, priced at $105 found 8 hours ago
Delta
Tue, Sep 15 - Tue, Oct 6
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$179 Roundtrip, found 8 hours ago
$179
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Sep 15 from Logan Intl. to Southwest Florida Intl., returning Tue, Oct 6, priced at $179 found 8 hours ago
American Airlines
Tue, Sep 15 - Wed, Sep 16
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 15 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Sep 16, priced at $189 found 2 days ago
Delta
Wed, Sep 16 - Tue, Sep 29
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 16 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Tue, Sep 29, priced at $197 found 4 days ago