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 gesamt für 3 Nächte

25.–28. Dez. 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 gesamt für 4 Nächte

21.–25. Okt. 2026

Gulf Access
Gulf Access
Gulf Access
Gulf Access
Gulf Access

Gulf Access

4 bedrooms·4½ baths
Longboat Key • Florida

60.500,00 $ USD gesamt für 30 Nächte

28. Sept. – 28. Okt. 2026

Pompano Palms
Pompano Palms
Pompano Palms
Pompano Palms
Pompano Palms

Pompano Palms

3 bedrooms·3½ baths
Palmetto • Florida
$71/ Nacht(zzgl. Gebühren & Steuern)
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 gesamt für 3 Nächte

4.–7. Okt. 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 gesamt für 182 Nächte

28. Sept. 2026 – 29. März 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 gesamt für 3 Nächte

16.–19. Okt. 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 gesamt für 3 Nächte

28. Sept. – 1. Okt. 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 gesamt für 3 Nächte

28. Sept. – 1. Okt. 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 gesamt für 7 Nächte

28. Sept. – 5. Okt. 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 gesamt für 7 Nächte

9.–16. Okt. 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 gesamt für 28 Nächte

31. März – 28. Apr. 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 gesamt für 3 Nächte

28. Sept. – 1. Okt. 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 gesamt für 120 Nächte

28. Sept. 2026 – 26. Jan. 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 gesamt für 3 Nächte

28. Sept. – 1. Okt. 2026

balcony + Gulf view
Living room with Gulf view
059-Unit 401-5
060-Unit 401-6
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 gesamt für 3 Nächte

29. Sept. – 2. Okt. 2026

Renovated Beach Paradise. Ground Floor unit 64 image 1
052-Unit 64-2
059-Unit 64-9
058-Unit 64-8
060-Unit 64-10

Turtle Crawl Inn 64

1 bedroom·1 bath
Longboat Key • Florida
4.88(73 reviews)

932,25 $ USD gesamt für 3 Nächte

28. Sept. – 1. Okt. 2026

Right on the beach.Renovated ground Floor unit 63. image 1
020-Unit 63-4
023-Unit 63-7
024-Unit 63-8
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 gesamt für 3 Nächte

28. Sept. – 1. Okt. 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 gesamt für 3 Nächte

8.–11. Okt. 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 gesamt für 3 Nächte

28. Sept. – 1. Okt. 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)

1.333,40 $ USD gesamt für 3 Nächte

28. Sept. – 1. Okt. 2026

Welcome to The Beach, Unit 222!
The Beach complex from the waterfront - only 15 units, nice and quiet!
Pleasant!
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 gesamt für 3 Nächte

28. Sept. – 1. Okt. 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 gesamt für 3 Nächte

28. Sept. – 1. Okt. 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 gesamt für 5 Nächte

11.–16. Okt. 2026