Oakes Estates Vacation Packages

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

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Top Holiday Package Deals in Oakes Estates

Price found within the past 48 hours. Click for updated prices.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Price was CA $1,522, price is now CA $1,121 per person
CA $1,121
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,024 reviews)
Love no me gusto es q no tiene playa

Reviewed on Jun 20, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $2,162, price is now CA $1,422 per person
CA $1,422
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,018 reviews)
Excellent. I will definitely come back

Reviewed on Jun 15, 2026

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Price was CA $2,598, price is now CA $1,761 per person
CA $1,761
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (359 reviews)
Very clean. Very safe. Family friendly. Very close to beach. Everything was really nice. Would recommend.

Reviewed on Jun 19, 2026

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Price was CA $1,940, price is now CA $1,323 per person
CA $1,323
per person
Jul 30 - Aug 6
found 1 hour ago
Roundtrip flight included
Montreal (YMQ) to Fort Myers (RSW)
9/10 Wonderful! (13 reviews)
Staff was extremely helpful and friendly during check-in, had gold cart transportation to our villa and back to the main building. The walk back and forth was beautiful along the water and only took about 3 min each way. We arrived late in the day and the restaurants were closing but the staff let us eat before close, they didn't have to but was very much appreciated! Food was amazing at the restaurants and the food court was also just as amazing. Room was beautiful with a beautiful view, balcony and super clean! Will definitely stay again and definitely recommend to stay here!

Reviewed on Jun 19, 2026

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $1,796, price is now CA $1,238 per person
CA $1,238
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,010 reviews)
Clean room. Nice pool area and great location to many restaurants

Reviewed on Jun 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

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

Oakes Estates 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 $277 per night from Jul 7 to Jul 8
CA $277
CA $380 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (2,237 reviews)
"I like everything"

Reviewed on Jun 20, 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
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Jul 5 to Jul 6
CA $197
CA $219 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,822 reviews)
"Love the studio link suite with the divider. It was like a separate bedroom still.."

Reviewed on Jun 20, 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 $207 per night from Jun 28 to Jun 29
CA $207
CA $230 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (1,457 reviews)
"My wife and I waited find a business salon, because we had to do business jobs about our business, but we didn't find it."

Reviewed on Jun 20, 2026

Hilton Naples
See all 10,595 properties in Oakes Estates
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
Family Vacations
Family Vacations

Frequently asked questions

How much does an Oakes Estates vacation package cost?
Discover the best of Oakes Estates from just CA $1,121. We offer a great selection of hotels, flights and rental cars to suit every style and budget. Score even more discounts when you add some sightseeing activities to your vacation package.
How do I get a cheap travel package to Oakes Estates?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got it all. Select a combination that best fits you and see your savings grow. Of course, a package deal is never a one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 hotels globally, which lets you customize your Oakes Estates adventure.
Where should I stay in Oakes Estates?
Most who travel to Oakes Estates put both Naples Pier and Barefoot Beach on their bucket lists. Why not choose a hotel within walking distance of these top attractions?
What are the top hotels in Oakes Estates?
If this will be your first time in Oakes Estates, secure a room at Newly Built Modern North Naples Villa On 3 Acres or Private Studio On 3 Acre Property In Paradise. Both hotels offer comfortable beds and are favorites among many savvy travelers.
How far in advance should I book my Oakes Estates vacation?
Reserving your flights early with Expedia means one less thing to have to worry about. Most carriers advertise prices up to 12 months prior to departure dates. This is usually the cheapest time to book. If circumstances have left you booking late, great deals to Oakes Estates are still known to appear just weeks before departure.
What does an Expedia Oakes Estates travel package include?
Flights, hotels and car rentals — we bring you the very best deals. All you'll have to do is pick your favorite combination. After you've made your booking, you can add on the fun stuff like experiences and tours. Our travel packages make it simple to craft an exciting Oakes Estates vacation.
What should I know before booking an Oakes Estates travel package?
You'll pick up impressive savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything together makes trip planning easier. So why waste your time or money? Whether you're organizing an upscale romantic escape or a budget family adventure, have a look at our package deals today.
Can I choose my airline with an Oakes Estates Expedia vacation package?
You can, and with more than 550 airlines to choose from worldwide, you've got lots of choice. Have a look through the available options and see which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Oakes Estates vacation package?
If your travel plans in Oakes Estates have been upended, it's good to know that you can amend or cancel your booking. If you made your booking in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. To learn more, check our Customer Service Portal.

Discover the most popular places to visit in Oakes Estates

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 Florida: Downtown Electric Trike Tour

Naples Florida: Downtown Electric Trike Tour - Family Fun

CA $82
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Trike Tour - Family Fun
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

CA $108
per adult
Naples: Sightseeing and Dining Cruises
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.