Ole Vacation Packages
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Top Holiday Package Deals in Ole
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
Price was CA $1,131, price is now CA $737 per person
CA $737
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (725 reviews)
Kev and bellmen Jon gave my family and I so much kindness and compassion during my stay and I will be forever grateful to them and all the staff at this property
Reviewed on Apr 11, 2026
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was CA $2,316, price is now CA $1,377 per person
CA $1,377
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,002 reviews)
Location right on beach is what you are paying for- the beach is beautiful and steps from the hotel. Staff is great and very friendly. Rooms are average and need maintenance. The light over the shower had water coming through it (scary) and the door to the room whistled when the wind blew. Food choices are limited and way over priced for the quality. Dinner at Balene was disappointing - my lobster was chewy. No other eating establishments are close enough to walk to so you have to either drive or order food if you don't want to eat onsite the entire time. Overall we had a nice time because we came for beach and sun, but would not stay here again.
Reviewed on Apr 11, 2026
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Price was CA $1,152, price is now CA $802 per person
CA $802
per person
Jun 5 - Jun 9
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.8/10 Exceptional! (1,146 reviews)
The ac kept the room cool
Housekeeping only come every other day but that was fine and they did a good job
Reviewed on Apr 9, 2026
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Price was CA $1,063, price is now CA $743 per person
CA $743
per person
Jun 4 - Jun 8
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.2/10 Wonderful! (2,293 reviews)
Nice pool areas and spa facilities!
Reviewed on Apr 12, 2026
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Price was CA $1,293, price is now CA $913 per person
CA $913
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (821 reviews)
Small selection of food options on site. Bar was understaffed. Pool and lazy river were wonderful.
Reviewed on Apr 9, 2026
Where to stay in Ole
Find the best Ole areas and neighborhoods for the activities you enjoy most. Learn more about Ole
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.
Ole Hotel Deals
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
The price is CA $305 per night from May 3 to May 4
CA $305
CA $416 total
May 3 - May 4
includes taxes & fees
9/10 Wonderful! (1,749 reviews)
Wonderful place! Perfect stay:)
Reviewed on Apr 11, 2026
Great Wolf Lodge Naples
3900 City Gate Blvd N. Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Apr 26 to Apr 27
CA $220
CA $245 total
Apr 26 - Apr 27
includes taxes & fees
9.4/10 Exceptional! (666 reviews)
Definitely bring a cooler with snacks and drinks when spending a few days here. Prices in lodge are very high.
Reviewed on Apr 10, 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 $127 per night from May 5 to May 6
CA $127
CA $141 total
May 5 - May 6
includes taxes & fees
8.2/10 Very Good! (1,900 reviews)
It was a good price for what we needed. The ability to park a truck and boat trailer was what sold us more than anything.
Reviewed on Apr 11, 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 Ole
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
4.5/5(102 reviews)
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
4.5/5(26 reviews)
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
Naples Florida: Downtown Electric Trike Tour - Family Fun
CA $96
per adult
100% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
CA $101
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.