Oakes Estates Holidays from £825

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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.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was £1,086, price is now £825 per person
£825
per person
13 Jun - 18 Jun
found 4 hours ago
Return direct flight included
London (LHR) to Fort Myers (RSW)
9.4/10 Exceptional! (776 reviews)
Food was great, two pools (family and adults only) the room was clean which is extremely important and a great view

Reviewed on 7 May 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 £1,093, price is now £863 per person
£863
per person
13 Jun - 18 Jun
found 4 hours ago
Return direct flight included
London (LHR) to Fort Myers (RSW)
9.8/10 Exceptional! (1,192 reviews)
place was immaculate beds for super comfy

Reviewed on 5 May 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 £1,276, price is now £1,050 per person
£1,050
per person
27 Jul - 31 Jul
found 20 hours ago
Return flight included
London (LON) to Fort Myers (RSW)
9/10 Wonderful! (1,001 reviews)
Nice, high end facility with friendly staff. Check in was easy, check out was easy, going to the beach was easy… very relaxing stay.

Reviewed on 4 May 2026

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Price was £1,391, price is now £1,164 per person
£1,164
per person
13 Jun - 18 Jun
found 4 hours ago
Return direct flight included
London (LHR) to Fort Myers (RSW)
8.8/10 Excellent! (336 reviews)
Very nice landscaping; all units are right on the beach, spacious 1 BR efficiency

Reviewed on 2 May 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was £1,293, price is now £1,134 per person
£1,134
per person
19 Jun - 22 Jun
found 11 hours ago
Return direct flight included
Manchester (MAN) to Fort Myers (RSW)
9/10 Wonderful! (846 reviews)
The resort is wonderful. Beware the high pressure sale to join the Hyatt Vacation Club. That made our stay less than we hoped for.

Reviewed on 5 May 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

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

Great Wolf Lodge Naples

Great Wolf Lodge Naples

3 out of 5
3900 City Gate Blvd N. Naples FL
Fully refundableReserve now, pay when you stay
The price is £211 per night from 12 May to 13 May
£211
12 May - 13 May
includes taxes & fees
9.4/10 Exceptional! (776 reviews)
Nice.

Reviewed on 8 May 2026

Great Wolf Lodge Naples
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is £186 per night from 28 May to 29 May
£186
28 May - 29 May
includes taxes & fees
9/10 Wonderful! (2,076 reviews)
Nice clean resort with friendly staff a winner for sure

Reviewed on 8 May 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
Fully refundableReserve now, pay when you stay
The price is £136 per night from 12 May to 13 May
£136
12 May - 13 May
includes taxes & fees
9/10 Wonderful! (1,463 reviews)
The staff at this place were EXTREMELY rude except for the staff that checked us in one out! We had breakfast at the Sundeck, the food was not made fresh it was prepared ahead of time and there was a confrontation between a staff member and a customer in we actually thought that someone was going ...

Reviewed on 8 May 2026

Lani Kai Beachfront Resort
See all 10,568 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 £825. 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

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
Fifth Avenue South

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
Naples Pier

Naples Pier

4.5/5(59 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

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

£39
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Everglades National Park: Pontoon Boat Tour & Boardwalk

Everglades National Park: Pontoon Boat Tour & Boardwalk

£45
per adult
Everglades National Park: Pontoon Boat Tour & Boardwalk
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

£57
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. Flight-inclusive packages are ATOL protected.