Oakes Estates Vacation Packages
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Top Holiday Package Deals in Oakes Estates
Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina
Price was CA $1,555, price is now CA $939 per person
CA $939
per person
Jun 30 - Jul 7
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,008 reviews)
We enjoyed our stay! Very convenient location, right on the water, clean with recently renovated rooms. We went for a girls weekend and loved it! The only thing I can’t rave about was they had very poor water pressure, not sure if it was because we were on an end unit, but it was a trickle out of the shower head which can be a little difficult if you have a lot of hair, no hairdryer in room, and wish they had a full sized mirror in the room. Regardless I would definitely recommend staying there! It’s a beautiful property!
Reviewed on Apr 14, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was CA $3,104, price is now CA $1,603 per person
CA $1,603
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,002 reviews)
Excellent location and hotel!
Reviewed on Apr 12, 2026
The Perry Hotel Naples
Price was CA $2,243, price is now CA $1,203 per person
CA $1,203
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (748 reviews)
Spectacular spot. New hotel hits all the right notes. Service was superb. The room was immaculate and had a tremendous view. The first level pool is huge. I swam laps every day. The showstopper though is the rooftop pool and bar. I watched the Masters in splendor with views east and west. Again service was great and the food was great too. Check it out.
Reviewed on Apr 17, 2026
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Price was CA $1,696, price is now CA $1,094 per person
CA $1,094
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (821 reviews)
spectacular place for a weekend!!
Reviewed on Apr 16, 2026
Casa Playa Beach Resort
Price was CA $2,001, price is now CA $1,297 per person
CA $1,297
per person
Jun 30 - Jul 7
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (175 reviews)
A big plus having chairs and umbrellas available.
Reviewed on Apr 15, 2026
Where to stay in Oakes Estates
Find the best Oakes Estates areas and neighborhoods for the activities you enjoy most. Learn more about Oakes Estates
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.
Oakes Estates Hotel Deals
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
The price is CA $309 per night from May 18 to May 19
CA $309
CA $414 total
May 18 - May 19
includes taxes & fees
9/10 Wonderful! (2,024 reviews)
Parking was easy- however there is an automatic vallet parking system that I missed. The daily charge is like $50 for it.
Reviewed on Apr 17, 2026
Great Wolf Lodge Naples
3900 City Gate Blvd N. Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from Apr 21 to Apr 22
CA $240
CA $266 total
Apr 21 - Apr 22
includes taxes & fees
9.4/10 Exceptional! (693 reviews)
Great place for kids. Stuff very friendly. A lot of activities for kids. 10/10, recommend for family with kids
Reviewed on Apr 17, 2026
La Quinta Inn & Suites by Wyndham Naples Downtown
1555 5th Ave S Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from May 10 to May 11
CA $142
CA $157 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (1,902 reviews)
All good
Reviewed on Apr 17, 2026
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.
Frequently asked questions
Discover the most popular places to visit in Oakes Estates
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.
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.
Vanderbilt Beach
If a restful vacation is part of your travel plans, Vanderbilt Beach might be the perfect place to seek out during your trip to North Naples.
Things to do
Flamingo Marina: Backcountry Boat Tour of the Everglades
CA $66
per adult
Everglades National Park: Pontoon Boat Tour & Boardwalk
CA $83
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.