Location

Dates

Guests

Vacation rentals in Anna Maria, Florida, United States

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

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+5mile to AMI & IMG+Kid Friendly

4 bedrooms·2 baths

Bradenton • Florida

5(114 reviews)

$1,578.09 USD total for 4 nights

Oct 21 – 25, 2026

Gulf Access

4 bedrooms·4½ baths

Longboat Key • Florida

$60,500.00 USD total for 30 nights

Sep 28 – Oct 28, 2026

Pompano Palms

3 bedrooms·3½ baths

Palmetto • Florida

$71/ night(excl. fees & taxes)

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

Oct 4 – 7, 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

Sep 28, 2026 – Mar 29, 2027

Just at the bottom of the stairs! The beach awaits...!

Welcome to Silver Sands, Unit 256 on Longboat Key!

We're right on the Gulf! No need to cross a busy street to get to the beach!

A bird's eye view!

Silver Sands Gulf Beach Resort -- iconic, well-known (and loved!), old Florida charm, located on Gulf of Mexico Dr., beach side, just 35 units!

Tropical Beach Condo!

1 bedroom·1 bath

Longboat Key • Florida

5(11 reviews)

$1,153.60 USD total for 3 nights

Oct 16 – 19, 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 28 – Oct 1, 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

Sep 28 – Oct 1, 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 28 – Oct 5, 2026

Front of house.

Wind Swept Pass a Grille- Beach is across the street.

Wind Swept Pass a Grille- Beach is across the street.

Beautiful day at the beach

Wind Swept Pass a Grille- Beach is across the street.

Wind Swept Pass a Grille- Beach is across the street.

2 bedrooms·2 baths

St. Pete Beach • Florida

4.99(71 reviews)

$3,653.65 USD total for 7 nights

Oct 9 – 16, 2026

Pass a Grille Historic Cottage- Beach is across the street.

Beach. Steps from the cottage

Cozy Kitchen. Small but lots of space to cook

Pass a Grille Historic Cottage- Beach is across the street.

Pass a Grille Historic Cottage- Beach is across the street.

Pass a Grille Historic Cottage- Beach is across the street.

1 bedroom·1 bath

St. Pete Beach • Florida

4.85(27 reviews)

$7,401.06 USD total for 28 nights

Mar 31 – Apr 28, 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

$819.25 USD $789.59 USD total for 3 nights

Sep 28 – Oct 1, 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 28, 2026 – Jan 26, 2027

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

$1,580.32 USD total for 3 nights

Sep 28 – Oct 1, 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)

$1,227.18 USD total for 3 nights

Sep 29 – Oct 2, 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 28 – Oct 1, 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)

$815.86 USD total for 3 nights

Sep 28 – Oct 1, 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)

$833.00 USD total for 3 nights

Oct 8 – 11, 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

Sep 28 – Oct 1, 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 28 – Oct 1, 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 28 – Oct 1, 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 28 – Oct 1, 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)

$3,735.88 USD total for 5 nights

Oct 11 – 16, 2026