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

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

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

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

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

View from front yard
Short walk to fishing pier
Fishing pier before hurricane Milton - now open but shorter than this photo.
Newly remodeled kitchen
Renovated Waterfront Home

Renovated Waterfront Home

3 bedrooms·2 baths
Osprey • Florida
4.4(5 reviews)

$1,394.40 USD total for 7 nights

Oct 20 – 27, 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

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

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

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

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

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

Osprey Harbor Village 216
Osprey Harbor Village 216
Osprey Harbor Village 216
Osprey Harbor Village 216
Osprey Harbor Village 216

Osprey Harbor Village 216

3 bedrooms·2 baths
Osprey • Florida

$8,340.00 USD total for 30 nights

Oct 20 – Nov 19, 2026

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)

$5,780.00 USD total for 30 nights

Oct 20 – Nov 19, 2026

Landscape lighting and firepit in the front of the house
View of the canal in the back of the house
Sunrise over the pool and covered outdoor seating.
Large pull out sectional facing the fireplace and flatscreen TV
Living room with pull out couch, flatscreen and dining table

Tropi-Casa

4 bedrooms·2 baths
Bradenton • Florida

$862.50 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

Family home on Golf Course image 1
Family home on Golf Course image 2
Pool
Family home on Golf Course image 4
Family home on Golf Course image 5

Family home on Golf Course

4 bedrooms·4 baths
Bradenton • Florida

$2,550.00 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

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)

$1,850.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

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

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

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

$3,160.41 USD $2,884.81 USD total for 5 nights

Oct 20 – 25, 2026

My Peaceful place on the bay. image 1
My Peaceful place on the bay. image 2
My Peaceful place on the bay. image 3
My Peaceful place on the bay. image 4
My Peaceful place on the bay. image 5

My Peaceful place on the bay.

2 bedrooms·2 baths
Bradenton • Florida
4.99(187 reviews)

$549.49 USD total for 3 nights

Oct 28 – 31, 2026

My Sunny home on the Bay. image 1
My Sunny home on the Bay. image 2
My Sunny home on the Bay. image 4
My Sunny home on the Bay. image 5
My Sunny home on the Bay. image 6

My Sunny home on the Bay.

2 bedrooms·2 baths
Bradenton • Florida
4.98(273 reviews)

$576.61 USD total for 3 nights

Oct 26 – 29, 2026

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

Oct 20 – 27, 2026