Timber Pines Vacation Packages 2026 from $548

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Your Timber Pines Vacation

With every last detail organized before you head off, our Timber Pines vacation packages mean you can simply focus on having a good time. Whether you're based in the neighborhood of Heritage Pines, which is great for golfing, or another part of town, this fun city promises a wealth of discoveries. If your trip to Timber Pines includes some sightseeing, don't miss renowned attractions like Weeki Wachee Springs, Weeki Wachee River and Weeki Wachee Springs State Park. Don't delay visiting this destination any longer. The ultimate Timber Pines vacation is a few quick clicks away with Expedia.

The Latest Timber Pines Vacation Packages

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

Hibiscus Suites - Gateway to Siesta Key

$548

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (2,455 reviews)

Room was very clean, all furniture looked like new. Stuff was pleasant. Nice furnished room, living room and small kitchen. Love it

Reviewed on Oct 20, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,788

per person

Dec 27 - Jan 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The hotel was beautiful. The rooms were very thought through and had everything you needed. The pool area hours were not late enough and guest parking needs improved those are the only things I would say I wished were better. Kristina at the front desk was amazing!

Reviewed on Oct 24, 2026

Stylish Treasure Island Escape

Sunshine Beach

$4,357

per person

Dec 4 - Dec 9

found 9 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

No reviews

CW Resort

Save 100% on your flight

$1,651

per person

Dec 27 - Jan 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Beautiful place to stay

Reviewed on Oct 23, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,160

per person

Jan 15 - Jan 19

found 11 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (604 reviews)

Beautiful old florida style resort Beautiful rooms comfortable beds right on the powdery white sand beach and turquoise water

Reviewed on Oct 18, 2026

Where to stay in Timber Pines

Find the best Timber Pines areas and neighborhoods for the activities you enjoy most. Learn more about Timber Pines

A field with tall grasses and a line of palm trees under a clear sky.

Weeki Wachee

1 out of top 10 points of interest in this area

Unique features of Weeki Wachee include the shopping and restaurants. Make a stop by Weeki Wachee Springs or Weeki Wachee Springs State Park while you're exploring the area.

A small island with Spanish moss-covered trees surrounded by calm water.

Shady Hills

Shady Hills might not have many top sights, but Adventure Coast Fun Park and Strong Tower Vineyard are two attractions nearby that you can check out.

Berkeley Manor

While Berkeley Manor isn't home to many top sights, Weeki Wachee Springs and Weeki Wachee Springs State Park are some notable places to visit nearby.

River Country Estates

While River Country Estates might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Weeki Wachee Springs State Park and Weeki Wachee Springs.

A winding forest path surrounded by trees and greenery.

Forest Oaks

Though Forest Oaks might not have many top sights, you can venture to the surrounding area to see attractions like Bowlero Spring Hill and Nature Coast Botanical Gardens.

Timber Pines Hotel Deals

La Vista Inn

11736 US HIGHWAY 19 Port Richey FL

Fully refundableReserve now, pay when you stay

$59 nightly

$66 total

Nov 24 - Nov 25

Total with taxes and fees

5.8/10 (1,003 reviews)

"Carlos is absolutely amazing! Great customer service!"

Reviewed on Oct 23, 2026

Motel 6 Spring Hill, FL - Weeki Wachee

6172 Commercial Way Spring Hill FL

Fully refundableReserve now, pay when you stay

$53 nightly

$59 total

Oct 29 - Oct 30

Total with taxes and fees

7.4/10 Good! (1,602 reviews)

"Don't have fridges or microwaves I only use it cus its cheap"

Reviewed on Oct 23, 2026

Comfort Inn & Suites New Port Richey Downtown District

6206 US HWY 19 New Port Richey FL

Fully refundable

$87 nightly

$98 total

Nov 1 - Nov 2

Total with taxes and fees

9.2/10 Wonderful! (1,491 reviews)

"Bathroom was not clean, the room smelled like someone had smoked cigarrettes in it. Pillows were very uncomfortable."

Reviewed on Oct 23, 2026

See all 1,459 properties in Timber Pines

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.