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.
Courtyard by Marriott Fort Myers Cape Coral

Courtyard by Marriott Fort Myers Cape Coral

3 out of 5
Price was CA $792, price is now CA $504 per person
CA $504
per person
Apr 22 - Apr 28
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.2/10 Very Good! (997 reviews)
Mattress and pillows.

Reviewed on Feb 15, 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 $3,993, price is now CA $2,312 per person
CA $2,312
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,000 reviews)
The best part is that this hotel is right on the beach. We only stayed two nights because this hotel is very expensive, and the restaurant is very expensive.

Reviewed on Feb 1, 2026

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was CA $1,680, price is now CA $1,044 per person
CA $1,044
per person
Apr 22 - Apr 27
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
This place is amazing

Reviewed on Feb 15, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was CA $2,569, price is now CA $1,673 per person
CA $1,673
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
Wonder people like Teri and Marcelo make this place special. So convenient to everything, Hyatt Regency Tarpon Bay is excellent! Spa manicure service is superb as well ( had a detailed and perfect manicure from Tetiana!) highly recommend!

Reviewed on Feb 14, 2026

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Price was CA $1,809, price is now CA $1,183 per person
CA $1,183
per person
Apr 22 - Apr 27
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,009 reviews)
Yes other than the fact that it was cold. Had a great time.

Reviewed on Feb 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
Six beautiful cultivated gardens, 2.5 miles of hiking trails and a restored nature preserve

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 $581 per night from Feb 17 to Feb 18
CA $581
CA $717 total
Feb 17 - Feb 18
includes taxes & fees
8.8/10 Excellent! (1,876 reviews)
Very clean and beautiful pool!

Reviewed on Feb 12, 2026

Margaritaville Beach Resort Fort Myers
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
The price is CA $413 per night from Feb 24 to Feb 25
CA $413
CA $491 total
Feb 24 - Feb 25
includes taxes & fees
8.8/10 Excellent! (1,217 reviews)
They charge $20 to park at the hotel each day that was quite a rip off

Reviewed on Feb 10, 2026

Lani Kai Beachfront Resort
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $583 per night from Mar 12 to Mar 13
CA $583
CA $715 total
Mar 12 - Mar 13
includes taxes & fees
8.8/10 Excellent! (2,020 reviews)
Th staff is fast, friendly, and efficient. The rooms are very da

Reviewed on Jan 30, 2026

Naples Grande Beach Resort
See all 10,752 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.
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Frequently asked questions

How much does an Oakes Estates vacation package cost?
Discover the best of Oakes Estates from just CA $504. 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

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
Vanderbilt beach in Naples, Florida

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.

Vanderbilt Beach
5th Avenue Shopping District which includes markets, street scenes and a city

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

Things to do

SEAS The Day with Pure Florida

Naples Sightseeing Boat Tour

CA $90
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Sunset Tour in Naples Bay on a New Godfrey- All included

Naples Sunset Cruise - Complimentary Charcuterie and wine

CA $150
per adult
100% of travellers recommend
Naples Sunset Cruise - Complimentary Charcuterie and wine
Wild Dolphin Boat Tour

Best of Marco Dolphin Tour

CA $136
per adult
Best of Marco Dolphin Tour
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.