Location

Dates

Guests

Vacation rentals in Bradenton Beach, Florida, United States

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

Sep 7, 2026 – Mar 8, 2027

Stunning Gulf Views, Elevator to All Floors, Mini Golf, Heated Pool/Spa

Fun in the sun starts here - Hosted by RentAnnaMaria

Sunset Views from Shore to Please! - Hosted by RentAnnaMaria

Shore to Please - Hosted by RentAnnaMaria

Amazing Views! Main Living Space (3rd Floor) - Elevator to All Floors - Hosted by RentAnna Maria

Shore to Please

5 bedrooms·4½ baths

Anna Maria • Florida

5(11 reviews)

$462 – $1,956/ night(excl. fees & taxes)

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

Sep 7 – 10, 2026

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

2 bedrooms·2 baths

Longboat Key • Florida

$25,878.00 USD total for 120 nights

Sep 7, 2026 – Jan 5, 2027

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

Sep 13 – 16, 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

Sep 7 – 10, 2026

balcony + Gulf view

Living room with Gulf view

Beachfront Escape – Private Balcony, Gulf Views image 5

Panoramic Gulf View with Amazing Sunset.

1 bedroom·1 bath

Longboat Key • Florida

4.87(223 reviews)

$1,266.73 USD total for 3 nights

Sep 23 – 26, 2026

Renovated Beach Paradise. Ground Floor unit 64 image 1

Turtle Crawl Inn 64

1 bedroom·1 bath

Longboat Key • Florida

4.88(73 reviews)

$932.25 USD total for 3 nights

Sep 22 – 25, 2026

Right on the beach.Renovated ground Floor unit 63. image 1

Right on the beach.Renovated ground Floor unit 63. image 5

Turtle Crawl Inn 63

0 bedrooms·1 bath

Longboat Key • Florida

4.74(88 reviews)

$781.96 USD total for 3 nights

Sep 7 – 10, 2026

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

$1,116.44 USD $1,071.92 USD total for 3 nights

Sep 12 – 15, 2026

Welcome to The Beach on Longboat Key, Unit 224!

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)

$1,333.40 USD total for 3 nights

Sep 7 – 10, 2026

Welcome to The Beach, Unit 222!

The Beach complex from the waterfront - only 15 units, nice and quiet!

View to the South - sit and stay a while!

Float the day away!

Condo with a View on Longboat Key

0 bedrooms·1 bath

Longboat Key • Florida

4.98(122 reviews)

$1,310.80 USD total for 3 nights

Sep 13 – 16, 2026

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

0 bedrooms·1 bath

Longboat Key • Florida

5(28 reviews)

$1,141.30 USD total for 3 nights

Sep 7 – 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

$1,532.16 USD total for 3 nights

Sep 7 – 10, 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

Sep 7 – 14, 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)

$150/ night(excl. fees & taxes)

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

Sep 7 – 10, 2026

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

2 bedrooms·2 baths

Longboat Key • Florida

$8,425.50 USD total for 60 nights

Sep 7 – Nov 6, 2026

Our home is in the left side of the picture.

The front of our home.

Established 2019

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

Sep 10 – 15, 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

$3,871.68 USD total for 3 nights

Sep 7 – 10, 2026

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

4 bedrooms·3 baths

Bradenton • Florida

$1,320.00 USD total for 3 nights

Sep 7 – 10, 2026

350 feet of waterfront and a pair that extended out 250 feet into the river.

The house all lite up at night. Very peaceful

The Blue Heron Riverfront Retreat

The Blue Heron Riverfront Retreat

The Blue Heron Riverfront Retreat

The Blue Heron Riverfront Retreat

4 bedrooms·4 baths

Ellenton • Florida

5(3 reviews)

$3,596.55 USD total for 5 nights

Oct 19 – 24, 2026

Free cancellation

Property grounds

Beautiful 2 Bed/2 Bath Cozy Cottage Retreat â Your Home Away From Home

1 bedroom·1 bath

Sarasota • Florida

$713.00 USD total for 3 nights

Sep 7 – 10, 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

Sep 7 – 10, 2026

Free cancellation