Oakes Estates Holidays

Book a Hotel + Flight or Car together to unlock savings

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

5/5(2 area reviews)

Beaches, shopping and restaurants are some highlights of East Naples. Make a stop by Fifth Avenue South or Naples Botanical Garden while you're exploring.

Find hotels in East Naples

Top hotels in Oakes Estates

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
The price is 4.941.199 ₫ per night from 14 Jan to 15 Jan
4.941.199 ₫
6.095.237 ₫ total
14 Jan - 15 Jan
includes taxes & fees
9/10 Wonderful! (1,100 reviews)
ANY TYPE FOOD IS AVAILABLE ON SIGHT FOR A PRICE ITS VERY CONVENIENT PLENTY OF OPTIONS .

Reviewed on 12 Jan 2026

Lani Kai Beachfront Resort
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive Naples FL
Fully refundable
The price is 12.258.429 ₫ per night from 19 Jan to 20 Jan
12.258.429 ₫
14.918.954 ₫ total
19 Jan - 20 Jan
includes taxes & fees
8.8/10 Excellent! (2,010 reviews)
staff courteous amenities extensive

Reviewed on 11 Jan 2026

Naples Grande Beach Resort
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is 5.886.883 ₫ per night from 14 Jan to 15 Jan
5.886.883 ₫
7.882.052 ₫ total
14 Jan - 15 Jan
includes taxes & fees
8.8/10 Excellent! (1,786 reviews)
Amazing stay! Everything was absolutely spectacular — from the spotless, comfortable room to the outstanding service. The staff was professional, warm, and attentive, and the overall atmosphere was elegant and relaxing. Truly a top-tier experience. Highly recommended, and we would definitely ...

Reviewed on 12 Jan 2026

Margaritaville Beach Resort Fort Myers
See all 10,726 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.

Frequently asked questions

How much does an Oakes Estates holiday package cost?
Discover the best of Oakes Estates from just . 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 holiday 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 1null000null000 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 favourites among many savvy travellers.
How far in advance should I book my Oakes Estates holiday?
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 favourite 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 holiday.
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 organising 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 holiday 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 holiday 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.

Popular places to visit

5th Avenue Shopping District featuring a city, street scenes and markets

Fifth Avenue South

During your trip to Naples, you can enjoy retail therapy at Fifth Avenue South. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Fifth Avenue South
Naples Beach

Naples Beach

Why not spend a care-free 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 featuring a beach and landscape views as well as a large group of people

Naples Pier

Naples Pier is just one of the places to see in Naples, so why not enjoy the other things to explore during your travels? Stroll along the seaside or seek out the golf courses.

Naples Pier