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South Naples Vacation Packages

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South Naples Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Lehigh Resort Club

Lehigh Resort Club

3.5 out of 5
Save 100% on your flight
Price was $794, price is now $495 per person
$495
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this golf aparthotel in Lehigh Acres. Enjoy free WiFi, free parking, and a golf course. Popular attractions Veterans Park and Cypress Pines Country Club are located nearby.
I like the hotel however needs upgrade they have bicycles and stuff but most they were flat or not working

Reviewed on Aug 20, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,398, price is now $1,342 per person
$1,342
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop 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.

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,361, price is now $831 per person
$831
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.
No problems

Reviewed on Aug 29, 2026

Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,149, price is now $714 per person
$714
per person
Nov 7 - Nov 14
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.

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $1,272, price is now $808 per person
$808
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 Bowman's Beach are located nearby.
Beautiful clean place room clean beds comfy everything just as described. No complaints will definitely visit again and stay there.

Reviewed on Aug 29, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Save 100% on your flight
Price was $1,083, price is now $720 per person
$720
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this aparthotel in Punta Gorda. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fishermen's Village and Military Heritage Museum are located nearby.
We thouroughly enjoyed our first stay at The Suites at Fishermans Wharf. We enjoyed it so much that we booked a second trip and joined up with friends that we found out live in the area. They also stayed at the resort and loved it as much as we did. Girlfriend and I plan to become regulars!

Reviewed on Aug 29, 2026

Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

3 out of 5
Save 100% on your flight
Price was $2,807, price is now $1,901 per person
$1,901
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this cottage in Bonita Springs. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Barefoot Beach and Bonita Springs Public Beach are located nearby.

Landing Furnished Apartments - Naples, FL

Landing Furnished Apartments - Naples, FL

4 out of 5
Save 100% on your flight
Price was $1,419, price is now $963 per person
$963
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly apartment in Naples. Enjoy free WiFi, a rooftop terrace, and a fitness center. Popular attractions Fifth Avenue South and Naples Beach are located nearby.

South Naples Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
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 $809, price is now $562 per person
$562
per person
Oct 15 - Oct 19
found 16 hours 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 $1,201, price is now $715 per person
$715
per person
Nov 10 - Nov 14
found 16 hours ago
Roundtrip 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 $954, price is now $675 per person
$675
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,118, price is now $795 per person
$795
per person
Sep 29 - Oct 3
found 10 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)

South Naples Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Latitude 26 Waterfront Resort & Marina

Latitude 26 Waterfront Resort & Marina

3 out of 5
Save 100% on your flight
Price was $934, price is now $489 per person
$489
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,398, price is now $1,342 per person
$1,342
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,361, price is now $831 per person
$831
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,149, price is now $714 per person
$714
per person
Nov 7 - Nov 14
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
Fri, Sep 25 - Fri, Oct 9
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$125 Roundtrip, found 2 days ago
$125
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Sep 25 from Hopkins Intl. to Southwest Florida Intl., returning Fri, Oct 9, priced at $125 found 2 days ago
Frontier Airlines
Mon, Nov 23 - Thu, Dec 3
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Nov 23 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Dec 3, priced at $163 found 2 days ago
Delta
Sat, Nov 7 - Tue, Nov 10
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$179 Roundtrip, found 1 hour ago
$179
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Nov 7 from Logan Intl. to Southwest Florida Intl., returning Tue, Nov 10, priced at $179 found 1 hour ago
Frontier Airlines
Fri, Sep 11 - Sun, Sep 13
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$187 Roundtrip, found 17 hours ago
$187
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Fri, Sep 11 from Philadelphia Intl. to Southwest Florida Intl., returning Sun, Sep 13, priced at $187 found 17 hours ago