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

$914.17 USD $879.76 USD total for 3 nights

Nov 8 – 11, 2026

Welcome to The Beach on Longboat Key, Unit 224!
Warm and cozy!
Located mid-island, gulfside!
It's the good life.
White sand and turquoise waters!

Condo With a View 4: On the Beach!

1 bedroom·1 bath
Longboat Key • Florida
4.96(26 reviews)

$994.40 USD total for 3 nights

Oct 20 – 23, 2026

Kitchen
Aerial
Guest Bedroom converted to a king bed
Beach Access
Living Area

Sea Club III #4 2B / 2B Direct Beachfront Condo by RVA

2 bedrooms·2 baths
Longboat Key • Florida

$1,820.00 USD total for 5 nights

Oct 20 – 25, 2026

Carriage homes, four to a building. Ours is bottom right with light blue car in driveway/garage area.
Enjoy fishing or kayaking from our lakes, this lake is connected to four other lakes accessible via kayak.
Spacious living room with Smart TV and the VIEW!!!
Living room
Private ground floor patio/lanai.

Resort Living Turnkey Carriage Home, waterfront

2 bedrooms·2 baths
Venice • Florida

$8,533.22 USD total for 90 nights

Oct 20, 2026 – Jan 18, 2027

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

Oct 20 – 23, 2026

Lush and tropical!
Welcome to Silver Sands on Longboat Key!
Stroll north or south on the beach or just sit and wait for the sunrise or sunset -- you've got time.
Silver Sands Gulf Beach Resort!
White sandy beach - ideal!

Tropical Beach Condo!

1 bedroom·1 bath
Longboat Key • Florida
5(11 reviews)

$994.40 USD total for 3 nights

Oct 20 – 23, 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)

$1,150.60 USD $1,104.12 USD total for 5 nights

Oct 30 – Nov 4, 2026

Beautiful Resort-Style Gran Paradiso Townhouse
Hot Tub
Gran Paradiso Community
Community Pool
Sports Courts

Beautiful Resort-Style Gran Paradiso Townhouse

3 bedrooms·2½ baths
Venice • Florida
$150/ night(excl. fees & taxes)
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

$4,572.09 USD total for 3 nights

Oct 20 – 23, 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)

$757.00 USD total for 3 nights

Nov 15 – 18, 2026

Close to beautiful Venice Beach
Close to beautiful Venice Beach
Close to beautiful Venice Beach
Close to beautiful Venice Beach
Close to beautiful Venice Beach

Close to beautiful Venice Beach

1 bedroom·1 bath
Venice • Florida

$240.00 USD total for 3 nights

Oct 20 – 23, 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

$1,820.00 USD total for 3 nights

Oct 20 – 23, 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(1 review)

$970.00 USD $902.50 USD total for 3 nights

Oct 20 – 23, 2026

Golf Course and Private Pool Views
Golf Course and Private Pool Views
Golf Course and Private Pool Views
Golf Course and Private Pool Views
Golf Course and Private Pool Views

Golf Course and Private Pool Views

2 bedrooms·2 baths
Manatee County • Florida

$13,700.00 USD total for 60 nights

Oct 20 – Dec 19, 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(24 reviews)

$470.00 USD total for 3 nights

Oct 20 – 23, 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

Oct 20, 2026 – Apr 20, 2027

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

Oct 20 – 23, 2026

Gulf Access
Gulf Access
Gulf Access
Gulf Access
Gulf Access

Gulf Access

4 bedrooms·4½ baths
Longboat Key • Florida

$2,000.00 USD total for 3 nights

Oct 20 – 23, 2026

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
Putting Green with adjustable Putters and Balls Available or Bring your Own

2 Homes, 1 Private Pool | Near IMG & AMI

4 bedrooms·3 baths
Bradenton • Florida

$1,053.25 USD total for 3 nights

Oct 20 – 23, 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

Oct 20 – 23, 2026

Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway

Hubbel Hideaway

4 bedrooms·3 baths
Bradenton • Florida

$1,603.00 USD total for 3 nights

Oct 22 – 25, 2026

Tropical Mediterranean Villa
Tropical Lanai Salt Water Pool - Jacuzzi
Cathedral Great Room
California King
Modern Kitchen

Villa Ocala

3 bedrooms·2 baths
Venice • Florida

$1,378.60 USD $1,322.38 USD total for 5 nights

Oct 20 – 25, 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)

$1,880.00 USD total for 3 nights

Dec 25 – 28, 2026

View of condo from Sarasota Bay.
View of complex from public beach/Coquina Beach
Community pool
Sunrise over Sarasota Bay from condo decks/bedroom/living room
Sunset of the Gulf from condo and public beach/Coquina Beach

Sunrise/Sunset

2 bedrooms·2 baths
Bradenton Beach • Florida

$2,815.25 USD total for 7 nights

Oct 20 – 27, 2026