Featured
Private courtyard patio with dining for 4.
Private courtyard patio
Courtyard patio
Exterior detail
Living area

Comforts of Home in Secure Gated Community Just 2 Miles from Anna Maria Island

2 bedrooms·2 baths
Bradenton • Florida
5(2 reviews)

$6,302.00 USD total for 30 nights

Nov 10 – Dec 10, 2026

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater
Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater
Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater
Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater
Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

6 bedrooms·4 baths
Bradenton • Florida

$2,296.00 USD total for 3 nights

Nov 10 – 13, 2026

Backyard Oasis: Dive into relaxation with a sparkling pool and spa, surrounded by lush greenery!
Exterior: Vibrant sunsets and lush greenery await you in this stunning Bradenton retreat!
Living room with leather sofa, chairs and coffee table
Fully equipped kitchen with stainless steel appliances including French Door refrigerator with water and ice maker in door, glass electric stove, oven, microwave, coffee maker, electric tea kettle, dishes, cooking and baking pans, pots
Wood dining table

Heated Pool, Spa, BBQ, Games, Fire Pit, Sleeps 10

3 bedrooms·2 baths
Bradenton • Florida
5(75 reviews)

$646.00 USD total for 3 nights

Nov 15 – 18, 2026

Welcome to Paradise
Welcome to Paradise
Welcome to Paradise
Welcome to Paradise
Welcome to Paradise

Welcome to Paradise

3 bedrooms·2 baths
Bradenton • Florida

$718.65 USD total for 3 nights

Nov 10 – 13, 2026

Brand new king bed
Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 2
Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 3
Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 4
Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 5

Luxury 2BR/2BA Condo Minutes from Beaches & IMG

2 bedrooms·2 baths
Bradenton • Florida
5(37 reviews)

$519.48 USD total for 3 nights

Nov 15 – 18, 2026

Casa Milly image 1
Casa Milly image 2
Casa Milly image 3
Casa Milly image 4
Casa Milly image 5

Casa Milly

2 bedrooms·1 bath
Bradenton • Florida
5(36 reviews)

$600.00 USD total for 3 nights

Nov 10 – 13, 2026

Sitting Area w/fireplace and desk
Floorplan layout
Workspace w/2GB Fiber Internet
Full kitchen w/new appliances
Coffee Bar w/K-cups, tea, sugar

Bradenton Boho Bungalow

3 bedrooms·2 baths
Bradenton • Florida

$1,008.00 USD total for 3 nights

Nov 10 – 13, 2026

Boutique Style:Hot Tub*Heated Pool*Game Rm*2 Kings
Magical screened in pool surrounded by twinkling lights and multiple seating options
Bright chef’s galley kitchen with stainless appliances & ample workspace.
King bed with supportive comfortable mattress, high end cotton sheets, dedicated workspace, dresser and TV, yoga mats, 2 robes and standing mirror
Stylish lounge with sectional, big TV & chic wallpaper accent

Boutique Style:Hot Tub*Heated Pool*Game Rm*2 Kings

3 bedrooms·2 baths
Bradenton • Florida
5(44 reviews)

$937.95 USD total for 3 nights

Nov 16 – 19, 2026

2 Homes, 1 Private Pool | Near IMG & AMI
2 Homes, 1 Private Pool | Near IMG & AMI
Jenga and the Washer game help let non-pool lovers still be part of the action.
The twilight is beautiful with no bugs and lots of time to have a night swim.
2 Homes, 1 Private Pool | Near IMG & AMI

2 Homes, 1 Private Pool | Near IMG & AMI

4 bedrooms·3 baths
Bradenton • Florida

$1,053.25 USD total for 3 nights

Nov 10 – 13, 2026

Community Pool & Courts
Condo 6 miles from breathtaking Anna Maria Island
Condo 6 miles from breathtaking Anna Maria Island
View from Lanai
Ground Floor Condo

Condo 6 miles from breathtaking Anna Maria Island

2 bedrooms·2 baths
Bradenton • Florida

$12,700.00 USD total for 182 nights

Nov 10, 2026 – May 11, 2027

IMG Academy, Heated Pool, Huge Game Room & Golf! image 1
IMG Academy, Heated Pool, Huge Game Room & Golf! image 2
IMG Academy, Heated Pool, Huge Game Room & Golf! image 3
IMG Academy, Heated Pool, Huge Game Room & Golf! image 4
IMG Academy, Heated Pool, Huge Game Room & Golf! image 5

Sunny Bradenton Oasis, Pool/ Near Beaches & Golf!

4 bedrooms·2 baths
Bradenton • Florida

$1,505.16 USD $1,441.20 USD total for 3 nights

Dec 11 – 14, 2026

Screened heated salt pool, hot tub and patio. Includes new smart TV, patio furniture, picnic table and chaise lounge chairs.
Relax in our bubbling, heated salt hot tub!
Beaches + Htd Pool/Spa + Fenced Yard + Game Room! image 3
Master bedroom with new king bed, smart TV, private attached bathroom, ceiling fan and double closets.
Bedroom offers 2 new twin beds and 1 new full bed. Also includes new smart TV and ceiling fan.

AMI Beaches + Heated Salt Pool + Spa + Large Yard

3 bedrooms·2 baths
Bradenton • Florida
5(49 reviews)

$1,650.00 USD total for 3 nights

Nov 15 – 18, 2026

Our home is in the left side of the picture.
The front of our home.
Sunset View
Established 2019
Entry

Craig House with Heated Pool

3 bedrooms·2 baths
Bradenton • Florida
4.8(107 reviews)

$1,437.32 USD $1,376.50 USD total for 5 nights

Jan 14 – 19, 2027

Private heated pool and spacious fenced backyard with artificial turf, colorful seating, and an outdoor dining area.
Bradenton Getaway | Pool & BBQ | Near the Island
Bradenton Getaway | Pool & BBQ | Near the Island
Bradenton Getaway | Pool & BBQ | Near the Island
Bradenton Getaway | Pool & BBQ | Near the Island

Bradenton Getaway | Pool & BBQ | Near the Island

3 bedrooms·2 baths
Bradenton • Florida

$1,258.00 USD total for 3 nights

Nov 10 – 13, 2026

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

9 bedrooms·3 baths
Bradenton • Florida

$5,249.19 USD total for 3 nights

Nov 10 – 13, 2026

Perfect Sarasota Getaway:Close to all /Heated Pool
Perfect Sarasota Getaway:Close to all /Heated Pool
Perfect Sarasota Getaway:Close to all /Heated Pool
Perfect Sarasota Getaway:Close to all /Heated Pool
Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

3 bedrooms·2 baths
Sarasota • Florida
4.89(18 reviews)

$1,406.85 USD total for 3 nights

Nov 10 – 13, 2026

Tiki Time!
Tiki Time-Beach Boutique Rentals
Spacious living area
Chefs dream! Gourmet kitchen
Beautiful dining room

Tiki Time

4 bedrooms·2½ baths
Bradenton • Florida

$1,342.25 USD total for 3 nights

Nov 10 – 13, 2026

Aerial shot of house and pool.
Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub
Aerial of patio & pool
Pool & outdoor area at night.
Pool & Hot tub at night.

Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub

3 bedrooms·2 baths
Bradenton • Florida
5(50 reviews)

$1,780.00 USD total for 3 nights

Feb 23 – 26, 2027

32” TV with streaming device Comfortable couch.
Kitchen, diningroom, livingroom area
Gulf Coast Paradise Hideaway
Queen bed, night stand with usb plug, and lamp. 32”TV with streaming device sits on top of Armoire with plenty of storage. Bedroom does have closet with hangers.
Gulf Coast Paradise Hideaway

Gulf Coast Paradise Hideaway

1 bedroom·1 bath
Palmetto • Florida

$989.85 USD $911.32 USD total for 7 nights

Nov 10 – 17, 2026

cozy private patio for your enjoyment
Welcome to Sea Turtle Cove!
Adjustable king size bed. Very comfortable.
Upgraded kitchen space with convection cooktop and lovely light. I added air fryer/toaster oven.
Sea Turtle Cove private oasis near beaches image 5

Sea Turtle Cove private oasis near beaches

1 bedroom·1 bath
Sarasota • Florida
4.94(70 reviews)

$432.00 USD total for 3 nights

Nov 10 – 13, 2026

Dive into your own private paradise! Welcome to your "Happy Place" with a private fully-fenced backyard, surrounded by mature palm trees and a spacious HEATED SALTWATER POOL, plus tons of color changing lights!
Covered patio with fire pit, dining area & BBQ—perfect evenings
The sunlit Family Room with sparkling swimming pool views, an expansive L-shaped couch, oversized ottoman, children's books, games, and Smart TV for endless entertainment options, make it the perfect hub for relaxation and family fun!
Screened pool oasis with loungers, travertine deck & sunset views
Stainless LG appliances Quartz countertops Child & baby-friendly amenities Fully Stocked

Heated Pool·Fenced ½-Acre·Kid+Dog Ready·5mi to AMI

4 bedrooms·2 baths
Bradenton • Florida
5(131 reviews)

$1,498.94 USD total for 4 nights

Nov 10 – 14, 2026

Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway

Hubbel Hideaway

4 bedrooms·3 baths
Bradenton • Florida

$1,800.00 USD total for 3 nights

Nov 10 – 13, 2026

Perfect place to relax, read a book, and cool down with a dip in crystal clear pool with water fall feature
Front of house
Front entry way
Sun Soaked Paradise - Heated Pool image 5
Living room with ample seating large television.

Sun Soaked Paradise - Heated Pool

3 bedrooms·2 baths
Bradenton • Florida
5(2 reviews)

$970.00 USD $902.50 USD total for 3 nights

Nov 10 – 13, 2026

Riverfront 4BR: Boat Dock, Heated Pool
Riverfront 4BR: Boat Dock, Heated Pool
Riverfront 4BR: Boat Dock, Heated Pool
Riverfront 4BR: Boat Dock, Heated Pool
Riverfront 4BR: Boat Dock, Heated Pool

Riverfront 4BR: Boat Dock, Heated Pool

4 bedrooms·4 baths
Ellenton • Florida
5(3 reviews)

$3,523.86 USD total for 5 nights

Nov 30 – Dec 5, 2026