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 $687, price is now CA $433 per person
CA $433
per person
Apr 16 - Apr 21
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.2/10 Very Good! (997 reviews)
The service was quick and the room was clean. I would stay there again

Reviewed on Feb 21, 2026

South Seas Resort

South Seas Resort

3.5 out of 5
Price was CA $2,757, price is now CA $1,779 per person
CA $1,779
per person
Apr 16 - Apr 21
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.4/10 Very Good! (1,001 reviews)
Room was good. Housekeeping did not exist.

Reviewed on Feb 23, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $2,657, price is now CA $1,724 per person
CA $1,724
per person
Apr 15 - Apr 20
found 18 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
The room was very clean and comfortable and the staff was great and friendly!

Reviewed on Feb 22, 2026

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Price was CA $1,691, price is now CA $1,112 per person
CA $1,112
per person
May 10 - May 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.4/10 Very Good! (1,005 reviews)
Room was clean, beds were comfortable. Hallways a little dated. Staff were very friendly. A lively spot on the water.

Reviewed on Feb 23, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was CA $1,450, price is now CA $975 per person
CA $975
per person
May 7 - May 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.8/10 Exceptional! (1,027 reviews)
Great. Awesome room n vuews

Reviewed on Feb 22, 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 $549 per night from Feb 26 to Feb 27
CA $549
CA $681 total
Feb 26 - Feb 27
includes taxes & fees
9/10 Wonderful! (1,901 reviews)
Very clean and a very happy atmosphere plus I love that you can bring your furry friend

Reviewed on Feb 23, 2026

Margaritaville Beach Resort Fort Myers
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 out of 5
1555 5th Ave S Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Mar 22 to Mar 23
CA $230
CA $255 total
Mar 22 - Mar 23
includes taxes & fees
8.2/10 Very Good! (1,850 reviews)
The check-in person we had was not very friendly, but ALL other staff were absolutely wonderful and accommodating. The room was very clean. The bed was comfortable. Breakfast was a step above what they referred to as a continental breakfast. Finally, the hotel was located within minutes of the beach, ...

Reviewed on Feb 23, 2026

La Quinta Inn & Suites by Wyndham Naples Downtown
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 $586 per night from Mar 12 to Mar 13
CA $586
CA $719 total
Mar 12 - Mar 13
includes taxes & fees
9/10 Wonderful! (2,030 reviews)
Place was very clean for how many people were at the hotel. Hotel staff is friendly and accommodating.

Reviewed on Feb 23, 2026

Naples Grande Beach Resort
See all 10,729 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
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Beach Vacations
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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 $433. 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

Vanderbilt beach in Naples, Florida

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.

Vanderbilt Beach
Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA

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.

Naples 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
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

CA $100
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
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
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.