Vineyards Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Vineyards Vacation

From its highlights to its hidden treasures, this city is best explored with a Vineyards vacation package. Find a place to stay in Pelican Bay, which is great for coastal beaches, shopping and dining. Eager to get out and explore? Naples Zoo at Caribbean Gardens, Tiburon Golf Club and Mercato are among the top-rated places to visit during your trip to Vineyards. Whatever your travel plans or budget, putting together a tailored Vineyards vacation is simple with Expedia.

Top Vineyards Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

CA $994
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,787 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

CA $1,582
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (1,099 reviews)
Windward Passage Resort

Windward Passage Resort

CA $1,286
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.8/10 Excellent! (11 reviews)
Clean, beachfront, great staff, close attractions

Reviewed on Sep 5, 2026

Casa Ybel Resort

Casa Ybel Resort

Mid Island
CA $1,529
per person
Oct 19 - Oct 26
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (417 reviews)
The property is super convenient the beaches across the street a volleyball pool and then a huge lighted pool. The rooms were very clean older but clean and very comfortable. Mine felt like a little apartment tiki bar downstairs is great. The food is good. The drinks were good. They do play music until about midnight so if you don’t like music till that time, this isn’t the place for you lol. We will definitely stay here again.

Reviewed on Aug 30, 2026

Landing Furnished Apartments - Naples, FL

Landing Furnished Apartments - Naples, FL

CA $1,591
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (9 reviews)

Ready to book your vacation to Vineyards?

Choose your dates

Vineyards Hotel Deals

La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

1555 5th Ave S Naples FL
Fully refundableReserve now, pay when you stay
CA $95
CA $106 total
Sep 20 - Sep 21
includes taxes & fees
La Quinta Inn & Suites by Wyndham Naples Downtown
The Perry Hotel Naples

The Perry Hotel Naples

12155 Tamiami Trail N Naples FL
Fully refundableReserve now, pay when you stay
CA $149
CA $234 total
Sep 7 - Sep 8
includes taxes & fees
The Perry Hotel Naples
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

1345 5th Avenue South Naples FL
Fully refundableReserve now, pay when you stay
CA $199
CA $221 total
Sep 27 - Sep 28
includes taxes & fees
Hyatt House Naples/5th Avenue
See all 11,316 properties in Vineyards
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.

What to do in Vineyards

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

CA $92
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

CA $102
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

CA $108
per adult
Naples: Sightseeing and Dining Cruises
See all activities in Vineyards

Frequently asked questions

How much does a Vineyards vacation package cost?
You can snap up a vacation package to this destination from CA $994 on Expedia. However, how much your vacation to Vineyards costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Vineyards?
If you're hoping to book a cheap Vineyards vacation package, consider travelling in January, February and August. You'll typically find better prices on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Vineyards?
We recommend planning a Vineyards vacation for around 2 days. This gives you enough time to visit top sights including La Playa Golf Club and Sun N Fun Lagoon, and check out neighbourhoods like Park Shore and Moorings. You might even be able to squeeze in a day trip beyond Vineyards.
How to find the best Vineyards package deals?
Bagging a cheap Vineyards package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most affordable Vineyards package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Vineyards vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Vineyards vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Vineyards?
If you're planning a spontaneous Vineyards vacation, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Vineyards?
  1. Choose your dates: What you want to do in Vineyards and your favourite season will help you decide when to travel.
  2. Set a budget: Factor in costs such as flights, food and transportation when working out how much to save for your trip to Vineyards. Then, pick a hotel that matches your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Determine how many days away: Start by making a list of all the sights and activities you'd like to experience in Vineyards. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Vineyards vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.