Pine Woods Vacations from $423

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Your Pine Woods Vacation

Book your vacation package to Pine Woods and prepare to experience its families and loads more. Whether you're searching for adventure or relaxation, it's waiting for you in this inviting neighborhood. Kick start your trip to Pine Woods by heading to nearby attractions such as Naples Zoo at Caribbean Gardens, Clam Pass Park and Artis-Naples. Don't just dream it — do it! Lock in your perfect Pine Woods vacation with Expedia and enjoy traveling your way.

The Latest Pine Woods Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Home2 Suites by Hilton Fort Myers Airport

Home2 Suites by Hilton Fort Myers Airport

3 out of 5
Save 100% on your flight
Price was $733, price is now $423 per person
$423
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (398 reviews)
was very clean love it. the room love the size ,staff nice help anything excellent

Reviewed on Nov 24, 2025

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $957, price is now $437 per person
$437
per person
Feb 15 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Very nice Staff is excellent.

Reviewed on Nov 24, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,169, price is now $602 per person
$602
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
The bed was very comfortable. The shower was clean and updated. We enjoyed the fire pits at night.

Reviewed on Nov 27, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,985, price is now $1,106 per person
$1,106
per person
Feb 16 - Feb 21
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
El personal súper amable y todo muy limpio,la habitación excelente

Reviewed on Nov 24, 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 $2,453, price is now $1,376 per person
$1,376
per person
Jan 2 - Jan 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,000 reviews)
Excellent Location and beach view. Excellent Restaurant. Room Toilet Plumbing issues continued although staff responded to the room quickly. Never seen a problem continuing to persist for our whole trip. Five separate times.

Reviewed on Nov 22, 2025

Black Friday Sale

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Where to stay in Pine Woods

Find the best Pine Woods areas and neighborhoods for the activities you enjoy most. Learn more about Pine Woods
Naples Botanical Garden showing a garden and a pond

East Naples

4/5(171 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 hotels in East Naples

Pine Woods Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive Naples FL
Fully refundableReserve now, pay when you stay
$313 nightly
The price is $348 total per night from Dec 17 to Dec 18
$348 total
Dec 17 - Dec 18
Total with taxes and fees
8.8/10 Excellent! (1,929 reviews)
THE STAFF AND ROOMS WERE GREAT. THE LOCATION IS CLOSE TO EVERYTHING AND ENJOYED THE FOOD AND DRINKS AT THE BAR EXCELLENT CHOICE OF BOURBONS

Reviewed on Nov 21, 2025

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
$101 nightly
The price is $112 total per night from Nov 30 to Dec 1
$112 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (1,756 reviews)
Check in was seamless and the room was clean!

Reviewed on Nov 22, 2025

La Quinta Inn & Suites by Wyndham Naples Downtown
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
11800 Coconut Cove Drive Bonita Springs FL
Fully refundable
$160 nightly
The price is $179 total per night from Dec 15 to Dec 16
$179 total
Dec 15 - Dec 16
Total with taxes and fees
9/10 Wonderful! (712 reviews)
Clean room! Wonderful lazy river! Had such a great vacation there!

Reviewed on Nov 25, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs
See all 11,486 properties in Pine Woods
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Pine Woods

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
Vanderbilt Beach

Vanderbilt Beach

4.5/5(313 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.

Vanderbilt 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

Things to do

Sunset Tour in Naples Bay on a New Godfrey- All included

Sunset Tour in Naples Bay on a New Godfrey- All included

$110
per adult
100% of travellers recommend
Sunset Tour in Naples Bay on a New Godfrey- All included
Wild Dolphin Boat Tour

Best of Marco Dolphin Tour

$100
per adult
Best of Marco Dolphin Tour
Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour

Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour

$127
per adult
Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco 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.