Vanderbilt Conners Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
  • Marina
    Aug 23 - Aug 30

    Matanzas Inn Bayside Resort and Marina + Flight

    Fort Myers Beach
    7 nights
    3.0 star property
    9.4/10 - Exceptional (1,012 reviews)
    "Very close to the beach, but far enough away to be quiet. Spacious room, great kitchenette."
    Reviewed June 8, 2026
    Roundtrip • Toronto (YYZ) - Fort Lauderdale (FLL)
    YYZ - FLL • Nonstop FLL - YYZ • Nonstop
    CA $1,561
    CA $1,115
    per traveller
    found 1 day ago
    Matanzas Inn Bayside Resort and Marina
  • On the beach, white sand
    Aug 23 - Aug 30

    GullWing Beach Resort + Flight

    South Island
    7 nights
    3.5 star property
    9.4/10 - Exceptional (951 reviews)
    "Updated bathrooms and kitchen"
    Reviewed May 31, 2026
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • Nonstop RSW - YYZ • Nonstop
    CA $1,780
    CA $1,138
    per traveller
    found 13 hours ago
    GullWing Beach Resort
  • 2 outdoor pools
    Aug 23 - Aug 30

    The Lighthouse Resort Inn & Suites + Flight

    Fort Myers Beach
    7 nights
    3.0 star property
    8.6/10 - Excellent (1,687 reviews)
    "Loved it!!!!!"
    Reviewed June 9, 2026
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • Nonstop RSW - YYZ • Nonstop
    CA $2,189
    CA $1,434
    per traveller
    found 13 hours ago
    The Lighthouse Resort Inn & Suites
  • Luxury House, Pool View | Pool
    Aug 23 - Aug 30

    A Wave From it All + Flight

    Siesta Isle
    7 nights
    2.0 star property
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • Nonstop RSW - YYZ • Nonstop
    CA $4,353
    CA $3,039
    per traveller
    found 13 hours ago
    A Wave From it All
  • Lounge
    Jul 11 - Aug 1

    Landing Furnished Apartments - Naples, FL + Flight

    Naples
    21 nights
    4.0 star property
    9.4/10 - Exceptional (3 reviews)
    "check out and check in through the app never loaded so it got. little confusing but overall great stay"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • Nonstop RSW - YYZ • Nonstop
    CA $3,899
    CA $2,751
    per traveller
    found 15 hours ago
    Landing Furnished Apartments - Naples, FL

Where to stay in Vanderbilt Conners

Find the best Vanderbilt Conners areas and neighborhoods for the activities you enjoy most. Learn more about Vanderbilt Conners
East Naples

East Naples

4/5(11 area reviews)

Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.

Find hotels in East Naples

Vanderbilt Conners Hotel Deals

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is CA $259 per night from Jun 24 to Jun 25
CA $259
CA $359 total
Jun 24 - Jun 25
includes taxes & fees
9/10 Wonderful! (2,193 reviews)
"Good"

Reviewed on Jun 10, 2026

Margaritaville Beach Resort Fort Myers
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South Naples FL
The price is CA $205 per night from Jun 24 to Jun 25
CA $205
CA $228 total
Jun 24 - Jun 25
includes taxes & fees
9/10 Wonderful! (1,779 reviews)
"It was a long walk from the Garage."

Reviewed on Jun 9, 2026

Hyatt House Naples/5th Avenue
Hilton Naples

Hilton Naples

4 out of 5
5111 Tamiami Trl N Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jun 24 to Jun 25
CA $208
CA $231 total
Jun 24 - Jun 25
includes taxes & fees
9.2/10 Wonderful! (1,455 reviews)
"The hotel was very clean and beautiful. The staff was friendly and helpful throughout our stay. We really enjoyed our experience and would definitely stay here again."

Reviewed on Jun 9, 2026

Hilton Naples
See all 12,535 properties in Vanderbilt Conners
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Family Vacations

Frequently asked questions

How much does a Vanderbilt Conners vacation package cost?
The most affordable Vanderbilt Conners package is , so your dream escape can become a reality — without burning a hole in your pocket. Bundle flights, hotels and car rentals to customize a package that matches your travel style.
How do I get a cheap travel package to Vanderbilt Conners?
Combine your flights and hotels, toss in extras such as a rental car or activities, and save with a Vanderbilt Conners vacation package. You won't just walk away with superb discounts on your trip — you'll have plenty of choice within your reach too. When you book through Expedia, you can choose from more than 550 airlines and 1,000,000 properties across the globe. Your affordable vacation begins right here, right now!
Where should I stay in Vanderbilt Conners?
A trip to Vanderbilt Conners isn't over until you've seen Naples Pier and Barefoot Beach. Book a room nearby for quick access to these fantastic sights.
How far in advance should I book my Vanderbilt Conners vacation?
While prices change frequently, we generally advise reserving your seat as early as possible. Many international airfares can be compared on Expedia up to a year in advance. If you're booking late, you may still get lucky. Low prices to Vanderbilt Conners sometimes occur only weeks before departure.
What does an Expedia Vanderbilt Conners travel package include?
Choose from a combination of flights, rental cars and hotels. Once you've made your booking, you can add some tours and activities. Want to pick your fare class? That's also easy to do. The choice is all yours when it comes to creating your ideal Vanderbilt Conners escape.
What should I know before booking a Vanderbilt Conners travel package?
You'll land excellent savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything in one place just makes things easier. So why waste your time or money? Whether you're putting together a ritzy romantic getaway or a low-cost family road trip, take a look at our vacation packages today.
Can I choose my airline with a Vanderbilt Conners Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're in control. We have more than 550 partner airlines worldwide, so you have loads of choice when organizing your Vanderbilt Conners escape.
If I'm not able to travel, can I cancel my Vanderbilt Conners vacation package?
Certainly, and we're here to help. You may be able to change or cancel your Vanderbilt Conners vacation package at no cost if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If your travel plans suddenly change, look up our Customer Service Portal for more information.

Discover the most popular places to visit in Vanderbilt Conners

Fifth Avenue South

Fifth Avenue South

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Fifth Avenue South
Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA

Naples Beach

Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.

Naples Beach
Naples Pier

Naples Pier

Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.

Naples Pier

Things to do

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

CA $92
per adult
94% of travellers recommend
Naples Sightseeing Boat Tour
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

CA $108
per adult
Naples: Sightseeing and Dining Cruises
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

CA $102
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
See all activities in Naples
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.