Title: Oakes Estates Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $630 Expedia.ca

[Hotels in Oakes Estates](https://expedia.ca/Oakes-Estates-Naples-Hotels.0-n553248635976480645-0.Travel-Guide-Filter-Hotels)[Flights to Naples](https://expedia.ca/Cheap-Flights-To-Naples.d602724.Travel-Guide-Flights)[Things to do in Naples](https://expedia.ca/Things-To-Do-In-Naples.d602724.Travel-Guide-Activities)[Oakes Estates Car Rentals](https://expedia.ca/Car-Rentals-In-Oakes-Estates.d553248635976480645.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248635976480645/ef0ef239-57fa-4848-8e50-4ffcf9523d2a.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Oakes Estates Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
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Plan, book, and manage your trip all in one place

## Top Holiday Package Deals in Oakes Estates

Price found within the past 48 hours. Click for updated prices.

![Candlewood Suites Fort Myers Sanibel Gateway by IHG](https://images.trvl-media.com/lodging/3000000/2300000/2292900/2292854/ee159443_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Candlewood Suites Fort Myers Sanibel Gateway by IHG

South Fort Myers

CA $630

per person

May 23 - May 30

found 15 hours ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

7.6/10 Good! (1,009 reviews)

Overall our stay was very nice!! The pool had limited sun due to the building obstructing it, bet the area was nice, clean and had a grill area. The free laundry facility was a great amenity! If I had any complaint it would be the shower head was a bit strong, sensitive skin or a child would not have done well with that. Very nice stay, I would go back there. It was a little difficult navigating to the hotel.

Reviewed on Mar 3, 2026

![LaPlaya Beach & Golf Resort - A Noble House Resort](https://images.trvl-media.com/lodging/1000000/30000/25200/25199/d2442103_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

CA $1,859

per person

May 14 - May 19

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

9/10 Wonderful! (1,002 reviews)

Loved our stay at La Playa! The staff were so friendly and helpful and the property had beautiful views of the beach.

Reviewed on Apr 4, 2026

![The Perry Hotel Naples](https://images.trvl-media.com/lodging/103000000/102390000/102386400/102386398/0ad2742c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Perry Hotel Naples

CA $793

per person

May 15 - May 18

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Fort Myers (RSW)

9.6/10 Exceptional! (725 reviews)

This hotel is a refreshing experience for a traveler.

Reviewed on Apr 1, 2026

![Matanzas Inn Bayside Resort and Marina](https://images.trvl-media.com/lodging/3000000/2670000/2665100/2665085/78d7ce83_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Matanzas Inn Bayside Resort and Marina

CA $721

per person

May 15 - May 18

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Fort Myers (RSW)

9.4/10 Exceptional! (1,021 reviews)

I stayed in room 142 - perfect for me as a single traveler. My only minor inconvenience was the noisy neighbor the first 2 nights - but that isn’t any fault of the Inn. Would recommend to my friends and family and already trying to figure out when I can come again!

Reviewed on Apr 4, 2026

![South Seas](https://images.trvl-media.com/lodging/1000000/50000/40800/40732/12012e65_edited_c1ce_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### South Seas

CA $2,417

per person

May 17 - May 24

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

8.4/10 Very Good! (1,001 reviews)

Website is deceiving, this is not a resort like advertised. It is individually owned places managed by a resort. You have to come prepared with food and water. Getting towels at pools by the condos were a constant problem. The views were beautiful and lots of great wildlife to enjoy watching.

Reviewed on Apr 4, 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](https://expedia.ca/Naples-Oakes-Estates.dx553248635976480645)

![East Naples](https://images.trvl-media.com/place/6177501/5f861be1-5382-48a5-99ea-10946f7b2f07.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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 hotel + flight trips in East Naples](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Naples&DestID=6177511&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![walking down the bridge of Baker park in Naples Florida in southwest Florida public park ](https://images.trvl-media.com/place/553248635975749203/5fdacfb7-94ce-4350-9d5b-8788aaea5743.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Central Naples

1 out of top 10 points of interest in this area

 If you're spending some time in Central Naples, Naples Zoo at Caribbean Gardens and Naples Grande Golf Club are top sights worth seeing. 

[Find hotel + flight trips in Central Naples](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Central%20Naples&DestID=553248635975749203&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![old city dock  in tropical Naples Florida; Shutterstock ID 155142134](https://images.trvl-media.com/place/6337317/773e6b3f-e6bb-40d2-8271-236a37a0dcaa.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Old Naples

3 out of top 10 points of interest in this area

5/5(25 area reviews)

 The stunning beaches and popular shops are just a few highlights of Old Naples. Make a stop by Fifth Avenue South or Naples Beach while you're exploring the area. 

[Find hotel + flight trips in Old Naples](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Old%20Naples&DestID=6337317&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Delnor Wiggins State Park - Panoramic aerial view](https://images.trvl-media.com/place/6177550/10d8a15d-ce96-43ef-bf31-e37eb5973c97.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Naples Park

 Located in North Naples, Naples Park is bounded by U.S. Route 41 and offers easy access to Vanderbilt Lagoon. Enjoy shopping at the nearby outdoor mall, The Mercato, for a delightful experience. 

[Find hotel + flight trips in Naples Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Naples%20Park&DestID=6177550&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Vanderbilt Beach](https://images.trvl-media.com/place/6065875/2d1b283b-31ba-4ddc-adeb-36fe90f32f9d.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Vanderbilt Beach

1 out of top 10 points of interest in this area

4.5/5(4 area reviews)

 While visiting Vanderbilt Beach, you might make a stop by sights like Vanderbilt Beach and Delnor-Wiggins Pass State Park. 

[Find hotel + flight trips in Vanderbilt Beach](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Vanderbilt%20Beach&DestID=553248635977184221&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Oakes Estates Hotel Deals

![Margaritaville Beach Resort Fort Myers ](https://images.trvl-media.com/lodging/96000000/95130000/95127000/95126992/09777b0c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Margaritaville Beach Resort Fort Myers 

251 Crescent Street Fort Myers Beach FL

CA $367

CA $480 total

May 5 - May 6

includes taxes & fees

9/10 Wonderful! (1,986 reviews)

The only issue is book through Expedia because the room that I thought I got was not the room I got when I got there and as far as the resort goes, they let too many people in from the public to the pool and the people that stay there don’t have a chair to sit on

Reviewed on Apr 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F05%2F2026&endDate=06%2F05%2F2026&selected=95126992&PinnedHotelID=95126992&HadPinnedHotel=true&regionId=553248635976480645)

![Great Wolf Lodge Naples](https://images.trvl-media.com/lodging/113000000/112020000/112014600/112014521/c6e60574_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Great Wolf Lodge Naples

3900 City Gate Blvd N. Naples FL

Fully refundableReserve now, pay when you stay

CA $222

CA $246 total

Apr 19 - Apr 20

includes taxes & fees

9.4/10 Exceptional! (638 reviews)

Supper comfortable

Reviewed on Apr 4, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=112014521&PinnedHotelID=112014521&HadPinnedHotel=true&regionId=553248635976480645)

![La Quinta Inn & Suites by Wyndham Naples Downtown](https://images.trvl-media.com/lodging/1000000/30000/24700/24612/3a0774b2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

La Quinta Inn & Suites by Wyndham Naples Downtown

1555 5th Ave S Naples FL

Fully refundableReserve now, pay when you stay

CA $143

CA $159 total

May 3 - May 4

includes taxes & fees

8.2/10 Very Good! (1,892 reviews)

Everything was good, but the pool needs a Little love

Reviewed on Apr 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=03%2F05%2F2026&endDate=04%2F05%2F2026&selected=24612&PinnedHotelID=24612&HadPinnedHotel=true&regionId=553248635976480645)

[See all 10,583 properties in Oakes Estates](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&regionId=553248635976480645)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does an Oakes Estates vacation package cost?

### How do I get a cheap travel package to Oakes Estates?

### Where should I stay in Oakes Estates?

### What are the top hotels in Oakes Estates?

### How far in advance should I book my Oakes Estates vacation?

### What does an Expedia Oakes Estates travel package include?

### What should I know before booking an Oakes Estates travel package?

### Can I choose my airline with an Oakes Estates Expedia vacation package?

### If I'm not able to travel, can I cancel my Oakes Estates vacation package?

### Discover the most popular places to visit in Oakes Estates

![Fifth Avenue South](https://images.trvl-media.com/place/6337227/652d7a23-0ecb-418a-b7cc-95f00eef6cc8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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.

[](https://expedia.ca/Fifth-Avenue-South-Old-Naples.d6337227.Vacation-Attraction)

![Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA](https://images.trvl-media.com/place/553248621565061337/c3e350a9-2166-42a1-bc09-fe8d70fa80a9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.ca/Naples-Beach-West-Naples.d553248621565061337.Vacation-Attraction)

![Vanderbilt beach in Naples, Florida](https://images.trvl-media.com/place/553248621532652404/2e032eea-d142-4ae9-80c9-a10de88f17a7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.ca/Vanderbilt-Beach-Vanderbilt-Beach.d553248621532652404.Vacation-Attraction)

### Things to do

![Naples Sightseeing Boat Tour](https://mediaim.expedia.com/localexpert/1343716/ac14e815-1432-4873-b606-0821d4890ff8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Naples Sightseeing Boat Tour

CA $90

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/naples-sightseeing-boat-tour.a1343716.activity-details)

![Naples Florida: Downtown Electric Trike Tour](https://mediaim.expedia.com/localexpert/47891159/6efb2442-2dc7-4d4b-aa54-fffa02778569.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Naples Florida: Downtown Electric Trike Tour - Family Fun

CA $96

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/naples-florida-downtown-electric-trike-tour-family-fun.a47891159.activity-details)

![Gulf of Mexico Sunset Cruise from Naples](https://mediaim.expedia.com/localexpert/1344546/f630ba30-182b-40d9-a356-41d6167ac3b3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Gulf of Mexico Sunset Cruise from Naples

CA $101

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/gulf-of-mexico-sunset-cruise-from-naples.a1344546.activity-details)

[See all activities in Naples](https://expedia.ca/things-to-do/search?rid=553248635976480645)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.