Oakes Estates Holidays from £724

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Your Oakes Estates Holiday

Reserving an Oakes Estates holiday package is a good way to become familiar with this neighbourhood. From its hot spots to its lesser-known gems, you'll be sure to uncover something new. Your trip to Oakes Estates wouldn't be complete without a visit to popular attractions nearby such as Tiburon Golf Club, North Collier Regional Park and Sun N Fun Lagoon. No matter what your dream Oakes Estates holiday looks like, you can make it a reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was £928, price is now £724 per person
£724
per person
30 Apr - 7 May
found 19 hours ago
Return flight included
London (LON) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Nice quiet and clean.

Reviewed on 9 Feb 2026

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was £1,401, price is now £934 per person
£934
per person
30 Apr - 7 May
found 19 hours ago
Return flight included
London (LON) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Very clean room with great view of estuary. Friendly staff. The only downside was that we were charged a $25 per day resort fee we were not expecting

Reviewed on 7 Feb 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was £1,838, price is now £1,327 per person
£1,327
per person
25 Apr - 2 May
found 1 day ago
Return direct flight included
Manchester (MAN) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
The hotel was amazing and super clean.

Reviewed on 8 Feb 2026

Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Punta Rassa
Price was £1,729, price is now £1,325 per person
£1,325
per person
25 Apr - 2 May
found 1 day ago
Return direct flight included
Manchester (MAN) to Fort Myers (RSW)
9.6/10 Exceptional! (361 reviews)
The room was perfect for just my husband and myself, but with my elderly mother in a wheelchair, the bed was too high, toilet was too low and wobbled. She slept on the couch, and it was so low we had to both help her off of it. The view we had the condo was awesome except for someone in a wheelchair😔

Reviewed on 19 Jan 2026

Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Daniels Corridor
Price was £1,110, price is now £858 per person
£858
per person
30 Apr - 7 May
found 19 hours ago
Return flight included
London (LON) to Fort Myers (RSW)
No reviews

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 Gulf Shores Marina or Fifth Avenue South while you're exploring.

Find hotels in East Naples

Top hotels in Oakes Estates

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is £241 per night from 10 Feb to 11 Feb
£241
10 Feb - 11 Feb
includes taxes & fees
8.8/10 Excellent! (1,851 reviews)
Very clean

Reviewed on 3 Feb 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 £237 per night from 10 Feb to 11 Feb
£237
10 Feb - 11 Feb
includes taxes & fees
8.8/10 Excellent! (1,207 reviews)
Great location!

Reviewed on 8 Feb 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 £363 per night from 10 Feb to 11 Feb
£363
10 Feb - 11 Feb
includes taxes & fees
8.8/10 Excellent! (2,025 reviews)
Th staff is fast, friendly, and efficient. The rooms are very da

Reviewed on 30 Jan 2026

Naples Grande Beach Resort
See all 10,756 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 travel package cost?
Get ready to book, because a trip to Oakes Estates starts from an enticing £724. When you combine your hotels, flights and car rentals into a travel package, you'll walk away with the best bargains.
If I'm not able to travel, can I cancel my Oakes Estates travel package?
Because we understand life is full of surprises, the answer is yes. For more information, visit our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it for free. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.
How do I get a cheap travel package to Oakes Estates?
If you love getting a great deal, combine your bookings into an Oakes Estates travel package. Whether you're chasing flights, hotels, rental cars or tours, you can browse and book everything in one place. You'll have plenty of choice at your fingertips as well. Expedia has more than 550 airlines and 1,000,000 properties around the globe to select from. Fly with who you prefer, stay where you like and save precious dollars — now that's the perfect holiday!
Does Expedia offer Book Now, Pay Later Oakes Estates holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has worked out a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a fantastic getaway without eating away at your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's monthly instalment plans. If paying small amounts each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your holiday over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Oakes Estates?
Most people who travel to Oakes Estates put both Barefoot Beach and Naples Pier on their to-do lists. Why not select a hotel that's close to these main attractions?
What are the top hotels in Oakes Estates?
Book a stay at Naples Grande Beach Resort. It's one of the area's most popular properties. Another top option in Oakes Estates is Hampton Inn - Naples - I-75.
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. Many air carriers advertise tickets up to a year in advance. Generally, this is the cheapest time to book. If circumstances have left you booking late, discount flights to Oakes Estates are still known to appear in the weeks leading up to departure.
What does an Expedia Oakes Estates travel package include?
Choose from a combination of flights, rental cars and hotels. Once you've made your booking, you can also add on experiences and tours. Want to pick your fare class? That's easily done too. The choice is yours when it comes to planning your perfect Oakes Estates escape.
What should I know before booking an Oakes Estates travel package?
When you book your flights, hotels and car rentals together, you'll be rewarded with incredible discounts. Whether you're planning a mountain getaway in a cabin or would rather stay in a fancy hotel in the city, Expedia will help make it happen.
Can I choose my airline with an Oakes Estates Expedia travel package?
Definitely. Expedia has over 550 airline partners to select from around the globe. With so many choices, finding the ideal carrier to fly you to Oakes Estates will be a breeze.

Popular places to visit

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

Fifth Avenue South

4/5(3 reviews)

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

4.5/5(52 reviews)

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

4.5/5(58 reviews)

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

Everglades National Park: Pontoon Boat Tour & Boardwalk

Everglades National Park: Pontoon Boat Tour & Boardwalk

£44
per adult
Everglades National Park: Pontoon Boat Tour & Boardwalk
SEAS The Day with Pure Florida

Naples Sightseeing Boat Tour

£48
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Wild Dolphin Boat Tour

Best of Marco Dolphin Tour

£73
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. Flight-inclusive packages are ATOL protected.