Vineyards Vacations from $260

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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.

The Latest Vineyards vacation packages

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 $439, price is now $260 per person
$260
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,003 reviews)
Safe and quiet place. Easy parking. Strongly recommend.

Reviewed on Aug 23, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $1,900, price is now $1,057 per person
$1,057
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,004 reviews)
I loved the beachfront access

Reviewed on Aug 27, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $881, price is now $508 per person
$508
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (398 reviews)
Great property with welcoming staff

Reviewed on Aug 28, 2025

Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Price was $449, price is now $274 per person
$274
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.2/10 Very Good! (1,006 reviews)
There is not truly a restaurant or cafe in this hotel.

Reviewed on Aug 24, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $603, price is now $383 per person
$383
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,474 reviews)
Love this place. We have been staying here for 24 years.

Reviewed on Aug 28, 2025

Don't see what you're looking for?
See all available trips from Columbus to Vineyards
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Discover the most popular places to visit in Vineyards

Naples Beach

Naples Beach

4.5/5(1,407 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.

Naples Beach
5th Avenue Shopping District which includes markets, street scenes and a city

Fifth Avenue South

4.5/5(45 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 featuring a sandy beach and landscape views as well as a large group of people

Naples Pier

4.5/5(1,161 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

What to do in Vineyards

SEAS The Day with Pure Florida

Naples Sightseeing Boat Tour

$64
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Cute Manatee

Manatee Sightseeing and Wildlife Boat Tour

$70
per adult
90% of travellers recommend
Manatee Sightseeing and Wildlife Boat Tour
Naples Florida: Downtown Electric Moped Tour

Naples Florida: Downtown Electric Moped Tour

$70
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Moped Tour
See all activities in Vineyards

Vineyards Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
$197 nightly
The price is $219 total per night from Sep 7 to Sep 8
$219 total
Sep 7 - Sep 8
Total with taxes and fees
Naples Grande Beach Resort
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 out of 5
1555 5th Ave S, Naples, FL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $79 total per night from Sep 8 to Sep 9
$79 total
Sep 8 - Sep 9
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Naples Downtown
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South, Naples, FL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $141 total per night from Sep 5 to Sep 6
$141 total
Sep 5 - Sep 6
Total with taxes and fees
Hyatt House Naples/5th Avenue
See all 10,797 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.

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Frequently asked questions

How much does a Vineyards vacation package cost?
You can snap up a vacation package to this popular destination from $260 on Expedia. However, how much your vacation to Vineyards costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Vineyards?
You can generally find lower rates and better availability in September, October and December. Take a look at our cheap Vineyards vacation packages and you could land some great off-season deals.
How many days is enough for Vineyards?
Typically, a handful of days is enough to tick off the major attractions during your Vineyards vacation. However, if you want to have time to kick back or take day tours, think about extending your trip.
How to find the best Vineyards package deals?
Start your search for a Vineyards package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Vineyards package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Vineyards adventure underway.
Is it cheaper to book a Vineyards vacation as a package?
You can enjoy significant savings on your next Vineyards break by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Vineyards?
If you've got your Vineyards travel dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Vineyards vacation packages?
Your Vineyards trip is meant to be a relaxing escape from your daily routine, not a source of money worries. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.