$51 Cheap flight deals from Port Charlotte (RSW) to Windermere (ORL)

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This Weekend's Flight Deals from Port Charlotte to Windermere

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Apr 25 - Mon, Apr 27
SRQ
Sarasota-Bradenton Intl.
MCO
Orlando Intl.
$354 Roundtrip, found 7 hours ago
$354
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Apr 25 from Sarasota-Bradenton Intl. to Orlando Intl., returning Mon, Apr 27, priced at $354 found 7 hours ago

Airfares from $51 One Way, $141 Round Trip from Port Charlotte to Windermere

Prices starting at $141 for return flights and $51 for one-way flights to Windermere were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, May 6 - Sat, May 9
RSW
Fort Myers
MCO
Orlando
$141 Roundtrip, found 4 days ago
$141
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, May 6 from Fort Myers to Orlando, returning Sat, May 9, priced at $141 found 4 days ago
Mon, Jun 1 - Wed, Jun 3
RSW
Fort Myers
MCO
Orlando
$149 Roundtrip, found 5 days ago
$149
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Jun 1 from Fort Myers to Orlando, returning Wed, Jun 3, priced at $149 found 5 days ago
Wed, May 6 - Sat, May 9
RSW
Fort Myers
MCO
Orlando
$151 Roundtrip, found 4 days ago
$151
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, May 6 from Fort Myers to Orlando, returning Sat, May 9, priced at $151 found 4 days ago
Sun, Jun 21 - Wed, Jun 24
RSW
Fort Myers
MCO
Orlando
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sun, Jun 21 from Fort Myers to Orlando, returning Wed, Jun 24, priced at $157 found 5 days ago
Sun, May 31 - Tue, Jun 2
RSW
Fort Myers
MCO
Orlando
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sun, May 31 from Fort Myers to Orlando, returning Tue, Jun 2, priced at $160 found 5 days ago

Windermere economy flight packages

Price found within the past 48 hours. Click for updated prices.
Home2 Suites by Hilton St. Augustine I-95
3.0-star property

Home2 Suites by Hilton St. Augustine I-95

8.8/10 Excellent! (1,001 reviews)

May 25 - May 29

4 night stay

Fort Myers (RSW) to Orlando (MCO)

Southwest Airlines • Roundtrip • Coach
Price was $562, price is now $427 per person
$427
per person
found 1 day ago
Fantastic c place but they need to not allow giant boats to take up multiple parking spaces because parking is tight there. Maxed out last night.

Reviewed on Jun 21, 2025

Inn at Camachee Harbor by Coolvacay
2.5-star property

Inn at Camachee Harbor by Coolvacay

9.4/10 Exceptional! (288 reviews)

May 25 - May 29

4 night stay

Fort Myers (RSW) to Orlando (MCO)

Southwest Airlines • Roundtrip • Coach
Price was $725, price is now $544 per person
$544
per person
found 1 day ago
This location is a much better value than any of the luxury hotel chains. Very relaxing and laid back setting.

Reviewed on Mar 9, 2025

Guy Harvey Resort on St Augustine Beach
3.0-star property

Guy Harvey Resort on St Augustine Beach

8.8/10 Excellent! (2,971 reviews)

May 25 - May 29

4 night stay

Fort Myers (RSW) to Orlando (MCO)

Southwest Airlines • Roundtrip • Coach
Price was $680, price is now $520 per person
$520
per person
found 1 day ago
I loved the place but a couple things stuck out, One is the gap between the bottom of doors connecting the room next door, you can hear your neighbors like they are in your room with you. Two is you can tell the bar is short staffed and struggling.

Reviewed on Mar 17, 2026

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More About Flying To Windermere from Port Charlotte

Route Information for Flights from Port Charlotte to Windermere

Origin Airport IATA Code
RSW
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Port Charlotte to Windermere

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.