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Hotels In Bradenton - Vacation Rentals in Woodbury

Better Than A 5 Star Hotel in The Villages From US $156
         

New
Villa
Better Than A 5 Star Hotel
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  • Parking
  • Pool

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Luxury Places to Stay in Woodbury

Over 432+ Luxury Places to Stay in or Near Woodbury
Lake Weir Condo in Summerfield From US $2,067
         

New
House
Lake Weir Condo
  • Air Conditioner
  • Pool
  • Security/Safety

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Escape to Luxury: Designer Pool Home in The Villages in The Villages From US $928
         

10.0 (22 Reviews)
House
Escape to Luxury: Designer Pool Home in The Villages
  • Air Conditioner
  • Parking
  • Pool

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Escape to Luxury in The Villages in The Villages From US $829
         

New
House
Escape to Luxury in The Villages
  • Air Conditioner
  • Parking
  • Pet Friendly

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Private Beach at Lakefront Summerfield Getaway! in Summerfield From US $620
         

10.0 (1 Review)
House
Private Beach at Lakefront Summerfield Getaway!
  • Air Conditioner
  • Parking
  • TV

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The Coconut Courtayrd-Private Pool& Tiki Hot Tub-Minutes From Fun-Walk 2 Golf in The Villages From US $570
         

10.0 (51 Reviews)
House
The Coconut Courtayrd-Private Pool& Tiki Hot Tub-Minutes From Fun-Walk 2 Golf
  • Air Conditioner
  • Parking
  • Pool

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Private Beach at Lakefront Summerfield Getaway! in Summerfield From US $498
         

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New
House
Private Beach at Lakefront Summerfield Getaway!
  • Parking
  • View
  • Private Beach

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Golf Course Retreat in The Villages with Water Views, Lanai & Prime Location in Lady Lake From US $495
         

New
House
Golf Course Retreat in The Villages with Water Views, Lanai & Prime Location
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Rhythm and Blues - 3/2 w/Golf Cart in Leesburg From US $473
         

8.4 (5 Reviews)
House
Rhythm and Blues - 3/2 w/Golf Cart
  • Air Conditioner
  • Parking
  • Pool

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Top-Rated Vacation Rentals with a Pool in Woodbury

Over 267+ Top-Rated Vacation Rentals with a Pool in or Near Woodbury
Hot Tub House Escape – 3BR in The Villages at Special Rates in The Villages From US $199
         

10.0 (118 Reviews)
House
Hot Tub House Escape – 3BR in The Villages at Special Rates
  • Air Conditioner
  • Parking
  • Pool

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Modern Comfort & Prime Location in The Villages – Golf Cart Included! in The Villages From US $237
         

10.0 (96 Reviews)
House
Modern Comfort & Prime Location in The Villages – Golf Cart Included!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautiful Sunsets with Pool & Dock on Lake Weir in Summerfield From US $425
         

10.0 (37 Reviews)
House
Beautiful Sunsets with Pool & Dock on Lake Weir
  • Air Conditioner
  • Parking
  • Pool

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BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED in The Villages From US $247
         

10.0 (36 Reviews)
House
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
  • Air Conditioner
  • Parking
  • Pool

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Poolside Oasis! Family-Friendly Summerfield Escape in Summerfield From US $339
         

10.0 (35 Reviews)
House
Poolside Oasis! Family-Friendly Summerfield Escape
  • Air Conditioner
  • Pool
  • TV

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Pool Home Excellent Location - 2 Gas Golf Carts in The Villages From US $294
         

10.0 (35 Reviews)
House
Pool Home Excellent Location - 2 Gas Golf Carts
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Villages FL Community w/Elec. Golf Cart. Restaurants, Shopping & Hospitals. in The Villages From US $117
         

10.0 (34 Reviews)
House
The Villages FL Community w/Elec. Golf Cart. Restaurants, Shopping & Hospitals.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Well appointed home welcomes you PLEASE NOTE: We are outside of The Villages in Oxford From US $271
         

10.0 (25 Reviews)
House
Well appointed home welcomes you PLEASE NOTE: We are outside of The Villages
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pet-Friendly Vacation Rentals in Woodbury

Over 159+ Pet-Friendly Vacation Rentals in or Near Woodbury
Sand Hill Crane Cottage in The Villages From US $144
         

10.0 (2 Reviews)
House
Sand Hill Crane Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

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Private Dog Park 4mi to Lake/Beach Legends Run in Marion County From US $211
         

9.8 (7 Reviews)
House
Private Dog Park 4mi to Lake/Beach Legends Run
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautiful 3/2 designer home, pet friendly, free WiFi, golf cart, hot tub in The Villages From US $187
         

9.2 (89 Reviews)
House
Beautiful 3/2 designer home, pet friendly, free WiFi, golf cart, hot tub
  • Air Conditioner
  • Parking
  • Pet Friendly

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DARLING 2 BEDROOM VILLA WITH ENCLOSED LANAI LARGE BACKYARD AND GOLF CART in The Villages From US $313
         

9.6 (25 Reviews)
Villa
DARLING 2 BEDROOM VILLA WITH ENCLOSED LANAI LARGE BACKYARD AND GOLF CART
  • Air Conditioner
  • Parking
  • Pet Friendly

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Great location between Sumter Landing/Spanish Springs. Golf cart included in The Villages From US $98
         

10.0 (18 Reviews)
Cottage
Great location between Sumter Landing/Spanish Springs. Golf cart included
  • Air Conditioner
  • Parking
  • Pet Friendly

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Great location.Climate-controlled lanai & NEW 2024 4-SEATER GOLF CART INCLUDED! in Lady Lake From US $170
         

10.0 (12 Reviews)
House
Great location.Climate-controlled lanai & NEW 2024 4-SEATER GOLF CART INCLUDED!
  • Air Conditioner
  • Pet Friendly
  • Pool

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Spectacular water and golf course views in The Villages From US $220
         

10.0 (11 Reviews)
Villa
Spectacular water and golf course views
  • Air Conditioner
  • Parking
  • Pet Friendly

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Charming 2bedRiverton Dr home in fantastic Polo Ridge, The Villages Fl 32162. in The Villages From US $226
         

10.0 (4 Reviews)
House
Charming 2bedRiverton Dr home in fantastic Polo Ridge, The Villages Fl 32162.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Woodbury

Over 72+ Large Vacation Homes & Villas in or Near Woodbury
Coconut Courtyard, Tiki Hot Tub, Private Pool & Courtyard Retreat in The Villages From US $315
         

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10.0 (4 Reviews)
Villa
Coconut Courtyard, Tiki Hot Tub, Private Pool & Courtyard Retreat
  • Air Conditioner
  • Parking
  • Pool

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EVERGREEN VILLA II Newly updated 2 bedroom 2 bath courtyard villa in The Villages From US $154
         

10.0 (13 Reviews)
Villa
EVERGREEN VILLA II Newly updated 2 bedroom 2 bath courtyard villa
  • Air Conditioner
  • Parking
  • Pool

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Live the Villages lifestyle in this 2 bedroom beauty in The Villages From US $175
         

10.0 (4 Reviews)
Villa
Live the Villages lifestyle in this 2 bedroom beauty
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  • Parking
  • TV

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Charming 2-bedroom villa with AC/WiFi in the friendliest town The Villages in The Villages From US $314
         

10.0 (2 Reviews)
Villa
Charming 2-bedroom villa with AC/WiFi in the friendliest town The Villages
  • Air Conditioner
  • Parking
  • Pool

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Villa with a view (golf & water) *newly remodeled in The Villages From US $205
         

10.0 (1 Review)
Villa
Villa with a view (golf & water) *newly remodeled
  • Air Conditioner
  • Pet Friendly
  • TV

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4 Bedroom Retreat Sleeps 11 with Dock on Lake Weir near The Villages & Orlando in Summerfield From US $415
         

9.8 (33 Reviews)
Cottage
4 Bedroom Retreat Sleeps 11 with Dock on Lake Weir near The Villages & Orlando
  • Air Conditioner
  • Parking
  • TV

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Discover Relaxation and Fun in a Charming Patio Villa with a Golf Cart! in The Villages From US $297
         

9.8 (6 Reviews)
Villa
Discover Relaxation and Fun in a Charming Patio Villa with a Golf Cart!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lake Days & Golf Outings: Summerfield Group Escape in Summerfield From US $361
         

9.6 (5 Reviews)
House
Lake Days & Golf Outings: Summerfield Group Escape
  • Air Conditioner
  • Parking
  • TV

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Wheelchair Accessible Vacation Homes in Woodbury

Over 2+ Wheelchair Accessible Vacation Homes in or Near Woodbury
Quiet Villa in The Villages near Savannah Center and Glenview Golf Course in The Villages From US $130
         

5.0 (6 Reviews)
House
Quiet Villa in The Villages near Savannah Center and Glenview Golf Course
  • Air Conditioner
  • View
  • Wheelchair Accessible

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PRIVATE HOME- 2 Rooms with queen bed and Twin bed Separate. Super Host 15 Years in The Villages From US $65
         

1.0 (1 Review)
House
PRIVATE HOME- 2 Rooms with queen bed and Twin bed Separate. Super Host 15 Years
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace

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Woodbury Vacation Rentals and Airbnb Places to Stay Under $200

Over 217+ Woodbury Vacation Rentals and Airbnb Places to Stay Under $200
< 1 Mi to Lake Weir: Quiet Summerfield Getaway in Summerfield From US $89
         

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9.4 (8 Reviews)
House
< 1 Mi to Lake Weir: Quiet Summerfield Getaway
  • Parking
  • Security/Safety
  • Sports/Activities

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Sunny Home in The Villages w/Lanai & Pool Access! in The Villages From US $164
         

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8.0 (4 Reviews)
Cottage
Sunny Home in The Villages w/Lanai & Pool Access!
  • Air Conditioner
  • Parking
  • Pool

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Spacious Home in Palo Alto Village – Golf Cart, Lanai & Prime Villages Location in The Villages From US $192
         

10.0 (47 Reviews)
House
Spacious Home in Palo Alto Village – Golf Cart, Lanai & Prime Villages Location
  • Air Conditioner
  • Parking
  • TV

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Beautiful Golf Front 3-2 on Glenview. Cable , WI-FI , Passes and Golf Cart ! in The Villages From US $96
         

10.0 (22 Reviews)
House
Beautiful Golf Front 3-2 on Glenview. Cable , WI-FI , Passes and Golf Cart !
  • Air Conditioner
  • Parking
  • Pool

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Newly Renovated 2BR/2BA + Golf Cart, WiFi & Streaming! in The Villages From US $169
         

10.0 (16 Reviews)
House
Newly Renovated 2BR/2BA + Golf Cart, WiFi & Streaming!
  • Air Conditioner
  • Parking
  • Pool

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Chatham Retreat, in The Villages From US $140
         

10.0 (14 Reviews)
House
Chatham Retreat,
  • Air Conditioner
  • Parking
  • Pool

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Welcome to Luxury Living in The Villages! Private Pool & Golf Course View in The Villages From US $186
         

10.0 (4 Reviews)
House
Welcome to Luxury Living in The Villages! Private Pool & Golf Course View
  • Air Conditioner
  • Pool
  • TV

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6 Mi to Lake Sumter Landing: Home w/Perks! in The Villages From US $163
         

10.0 (4 Reviews)
House
6 Mi to Lake Sumter Landing: Home w/Perks!
  • Air Conditioner
  • Parking
  • Pool

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Instantly Bookable Vacation Homes in Woodbury

Over 221+ Instantly Bookable Vacation Homes in or Near Woodbury
The Villages FL Community w/Elec. Golf Cart. Restaurants, Shopping & Hospitals. in The Villages From US $420
         

10.0 (21 Reviews)
House
The Villages FL Community w/Elec. Golf Cart. Restaurants, Shopping & Hospitals.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Recently Updated Home Where Comfort and Convenience Meet Tranquility in The Villages From US $234
         

9.6 (5 Reviews)
House
Recently Updated Home Where Comfort and Convenience Meet Tranquility
  • Air Conditioner
  • Parking
  • Pool

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Cheerful 3 bedroom home with free parking. in Summerfield From US $243
         

10.0 (18 Reviews)
House
Cheerful 3 bedroom home with free parking.
  • Air Conditioner
  • Parking
  • TV

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Paradise on the Preserve w/hot tub and golf cart in The Villages From US $241
         

10.0 (10 Reviews)
House
Paradise on the Preserve w/hot tub and golf cart
  • Air Conditioner
  • Parking
  • TV

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Totally renovated bathrooms,kitchen, floors,bedrooms,by professional tradesmen in The Villages From US $270
         

10.0 (9 Reviews)
House
Totally renovated bathrooms,kitchen, floors,bedrooms,by professional tradesmen
  • Air Conditioner
  • Parking
  • Pool

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Sunset on Turtle Preserve - 3/2 in The Village of Woodbury in Leesburg From US $265
         

10.0 (9 Reviews)
House
Sunset on Turtle Preserve - 3/2 in The Village of Woodbury
  • Air Conditioner
  • Parking
  • Pool

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Peaceful and Private Lake Weir Home in Summerfield From US $331
         

10.0 (5 Reviews)
House
Peaceful and Private Lake Weir Home
  • Air Conditioner
  • Parking
  • TV

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Relax and Play in Paradise, Golf, Tennis, pools and Live entertainment in The Villages From US $265
         

10.0 (4 Reviews)
House
Relax and Play in Paradise, Golf, Tennis, pools and Live entertainment
  • Air Conditioner
  • Parking
  • Pool

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About Woodbury Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Hotelsinbradenton Woodbury, 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 Woodbury. Places to stay near Woodbury are 204.51 ft² on average, with prices averaging US $156 a night.

Hotelsinbradenton makes it easy and safe to find and compare vacation rentals in Woodbury 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 Woodbury

Type Count
Villas 1

Use these Quick Filters to Find a Vacation Rental in Woodbury

★ Pro Tip: Hotelsinbradenton makes it easy to compare the best listings on Hotelsinbradenton homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Hotelsinbradenton 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 Woodbury.

Weather in Woodbury

View the weather forecast for Woodbury before booking your Woodbury 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

Woodbury Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Woodbury?

There are a lot of options in Woodbury. If you plan on staying in the Woodbury area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Woodbury:

How many vacation rentals are available in Woodbury?

Currently, the total number of properties listed in 2026 is over 1 in the Woodbury area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Woodbury.