Stay If You Dare - Vacation Rentals in Woodlands

Gorgeous 3 bed 3 bath home From US $476
         

9.8 (137 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
1 Block to Downtown - 7 min to beach - King bed & Free parking From US $148
         

New Port Richey Downtown 🌴 From US $165
         

9.4 (34 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Paradise on the Gulf includes free pontoon boat for your stay. From US $487
         

Luxury Places to Stay in Woodlands

Over 528+ Luxury Places to Stay in or Near Woodlands
Beautiful updated Condo on the Lake From US $1,568
         

New
Condo
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Luxury Waterfront Oasis From US $777
         

New
House
  • Wellness Facilities
  • Fireplace/Heating
  • Child Friendly
Blue Shores From US $749
         

|
8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Woodlands

Over 163+ Top-Rated Vacation Rentals with a Pool in or Near Woodlands
Paradise on the Gulf! FREE pontoon boat use and salt water pool. From US $431
         

Tropical Tiny House From US $167
         

10.0 (55 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Woodlands

Over 217+ Pet-Friendly Vacation Rentals in or Near Woodlands
Riverfront Home w/Putting Green & Boat Dock! From US $218
         

Dockside Nook | Waterfront, Dock, Heated Pool From US $751
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Riverfront Home w/Putting Green & Boat Dock! From US $292
         

10.0 (22 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Cotee River Tiki Hut From US $126
         

10.0 (21 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunsational Seahorse- Nice and Relaxing 2/2 Sleeps 6 From US $151
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Woodlands

Over 44+ Large Vacation Homes & Villas in or Near Woodlands
Waterfront Gulf Getaway From US $585
         

New
House
  • Fireplace/Heating
  • Child Friendly
Dockside Nook | Fishing, Golf Cart, Heated Pool From US $463
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Delightful house in New Port Richey perfect for your getaway From US $132
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Wheelchair Accessible Vacation Homes in Woodlands

Over 22+ Wheelchair Accessible Vacation Homes in or Near Woodlands
Riverfront Getaway w/Hot Tub & Game Room! From US $201
         

The Hacienda From US $121
         

|
9.6 (870 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Lovely 3 bedroom pool home sleeps up to 8! From US $337
         

Woodlands Vacation Rentals and Airbnb Places to Stay Under $200

Over 284+ Woodlands Vacation Rentals and Airbnb Places to Stay Under $200
Castaway on Treasure Island NPR From US $145
         

|
10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • View
Downtown Bungalow #1 From US $138
         

10.0 (61 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Mermaid Studio From US $129
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming 1-Bedroom Oasis in the Heart of Downtown From US $123
         

The Flamingo on the Cotee River From US $159
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Instantly Bookable Vacation Homes in Woodlands

Over 274+ Instantly Bookable Vacation Homes in or Near Woodlands
Canal-Front Gulf Coast Getaway From US $251
         

10.0 (20 Reviews)
House
  • Air Conditioner
  • Pool
  • TV
We are the coolest hosts on the planet! You will love it here! From US $179
         

10.0 (9 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Gulf Coast Waterfront Home! From US $170
         

10.0 (9 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
Private House with Heated Pool, Close to Attractions! From US $242
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Walk Everywhere! 1-Bedroom Gem in Downtown Hub From US $119
         

About Woodlands Vacation Rentals

With more than 537 Woodlands vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Stayifyoudare and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Woodlands.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Stayifyoudare Woodlands, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Woodlands. Places to stay near Woodlands are 768.44 ft² on average, with prices averaging US $234 a night.

Stayifyoudare makes it easy and safe to find and compare vacation rentals in Woodlands with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Woodlands

Type Count
Vacation Homes 443
Holiday Apartments 42
Cottages 14
Hotels 13
B&B 2
Cabin Rentals 1
Others 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Woodlands

Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Woodlands.

Weather in Woodlands

View the weather forecast for Woodlands before booking your Woodlands Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay Near Woodlands, FL


Woodlands Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Woodlands?
How many vacation rentals are available in Woodlands?

Currently, the total number of properties listed in 2026 is over 537 in the Woodlands area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Woodlands.