$59 Cheap flight deals from Naples (APF) to Kissimmee (ORL)

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This Weekend's Flight Deals from Naples to Kissimmee

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.

Sun, Sep 13 - Tue, Sep 15
RSW
Southwest Florida Intl.
MCO
Orlando Intl.
$457 Roundtrip, found 2 days ago
$457
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Sep 13 from Southwest Florida Intl. to Orlando Intl., returning Tue, Sep 15, priced at $457 found 2 days ago

Airfares from $59 One Way, $117 Round Trip from Naples to Kissimmee

Prices starting at $117 for return flights and $59 for one-way flights to Kissimmee were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jan 9 - Sat, Jan 16
RSW
Fort Myers
MCO
Orlando
$117 Roundtrip, found 6 hours ago
$117
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Jan 9 from Fort Myers to Orlando, returning Sat, Jan 16, priced at $117 found 6 hours ago
Sat, Jan 9 - Sat, Jan 16
RSW
Fort Myers
MCO
Orlando
$127 Roundtrip, found 6 hours ago
$127
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Jan 9 from Fort Myers to Orlando, returning Sat, Jan 16, priced at $127 found 6 hours ago
Fri, Oct 30 - Wed, Nov 4
RSW
Fort Myers
MCO
Orlando
$136 Roundtrip, found 6 days ago
$136
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Oct 30 from Fort Myers to Orlando, returning Wed, Nov 4, priced at $136 found 6 days ago
Sat, Jan 9 - Sat, Jan 16
RSW
Fort Myers
MCO
Orlando
$138 Roundtrip, found 6 hours ago
$138
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Jan 9 from Fort Myers to Orlando, returning Sat, Jan 16, priced at $138 found 6 hours ago
Fri, Oct 30 - Wed, Nov 4
RSW
Fort Myers
MCO
Orlando
$146 Roundtrip, found 6 days ago
$146
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Oct 30 from Fort Myers to Orlando, returning Wed, Nov 4, priced at $146 found 6 days ago

Kissimmee economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Local - St. Augustine
2.0-star property

The Local - St. Augustine

8.2/10 Very Good! (303 reviews)

Nov 1 - Nov 7

6 night stay

Fort Myers (RSW) to Orlando (MCO)

Southwest Airlines • Roundtrip • Coach
Price was $562, price is now $395 per person
$395
per person
found 9 hours ago
I wasn’t thrilled with the room or the check in process. Texting and calling and waiting for a code seems unnecessary when they can just send you a code at check in time. The pillow in my room had a gross stain or substance on it and the floor was covered in slippery residue - probably from cleaning. The towels were mismatched and old. I was disappointed as a Local because I have driven by it so many times and thought it would be a neat place to stay. Also, the price does not match the accommodation provided.

Reviewed on Sep 6, 2026

The Kenwood Inn
3.5-star property

The Kenwood Inn

9.6/10 Exceptional! (400 reviews)

Nov 1 - Nov 7

6 night stay

Fort Myers (RSW) to Orlando (MCO)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,347, price is now $991 per person
$991
per person
found 9 hours ago
This was a very cute B&B. We brought our 2 small dogs. The location was great, and the breakfast was delicious. Would recommend:)

Reviewed on Sep 8, 2026

Casablanca Inn on the Bay
3.5-star property

Casablanca Inn on the Bay

8.8/10 Excellent! (1,003 reviews)

Nov 1 - Nov 7

6 night stay

Fort Myers (RSW) to Orlando (MCO)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,371, price is now $1,010 per person
$1,010
per person
found 9 hours ago
Amazing experience, room well cleaned. Cozy Very helpful courteous staff. Very strong Wi-Fi connection. Parking provided. Centrally located, walking distances to absolutely every where.

Reviewed on Sep 8, 2026

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More About Flying To Kissimmee from Naples

Route Information for Flights from Naples to Kissimmee

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

Naples to Kissimmee

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Discount Travel Planning Made Simple

You will have no problems finding budget flights from Naples to Kissimmee on Orbitz.com. If your travel plans are flexible, you can search for fares three days before and after a specific date to find the best price.

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.