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Vacation rentals in Anna Maria, Florida, United States

Experience the magic of evenings at Hayes House. The fire table creates a warm, welcoming gathering place where family and friends can unwind after a day at the beach or pool.

Relax in your private heated pool within a screened lanai. Whether you're swimming or lounging poolside, this backyard oasis is perfect for every season.

Gather at the Hayes House outdoor bar, complete with seating, a large TV, Bluetooth speakers, and fun coastal décor. It's the perfect spot to enjoy drinks, watch the game, listen to music, or unwind after a day at the beach.

One of the most loved features at Hayes House, the private heated pool offers the perfect escape for cooling off or simply soaking in the Florida sunshine.

Relax in the spacious living room featuring comfortable seating, a large Smart TV, original hardwood floors, and a decorative fireplace—perfect for movie nights, conversations, or unwinding after a day of adventure.

Group Oasis: Pool, Hot Tub & 6 Queen Beds

6 bedrooms·4 baths

Palmetto • Florida

5(4 reviews)

$ 2.126,00 USD totaal voor 3 nachten

29 nov – 2 dec 2026

Private courtyard patio with dining for 4.

Private courtyard patio

Courtyard patio

Exterior detail

Comforts of Home in Secure Gated Community Just 2 Miles from Anna Maria Island

2 bedrooms·2 baths

Bradenton • Florida

5(2 reviews)

$ 6.302,00 USD totaal voor 30 nachten

18 nov – 18 dec 2026

Beachfront Pass-a-Grille 2BR, Gulf Views

Front of house.

Beachfront Pass-a-Grille 2BR, Gulf Views

Beachfront Pass-a-Grille 2BR, Gulf Views

Beautiful day at the beach

Beachfront Pass-a-Grille 2BR, Gulf Views

2 bedrooms·2 baths

St. Pete Beach • Florida

4.99(71 reviews)

$ 3.614,88 USD totaal voor 7 nachten

10–17 dec 2026

Beachfront Cottage for 2: Pass-a-Grille

Beachfront Cottage for 2: Pass-a-Grille

Beachfront Cottage for 2: Pass-a-Grille

Beachfront Cottage for 2: Pass-a-Grille

Beach. Steps from the cottage

Beachfront Cottage for 2: Pass-a-Grille

1 bedroom·1 bath

St. Pete Beach • Florida

4.85(27 reviews)

$ 7.086,07 USD totaal voor 28 nachten

1–29 dec 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

$ 1.151,47 USD $ 1.105,19 USD totaal voor 3 nachten

11–14 dec 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 totaal voor 120 nachten

18 nov 2026 – 18 mrt 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

$ 2.825,76 USD totaal voor 3 nachten

18–21 nov 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 totaal voor 3 nachten

29 nov – 2 dec 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)

$ 1.022,65 USD totaal voor 3 nachten

28 nov – 1 dec 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)

$ 836,20 USD totaal voor 3 nachten

30 nov – 3 dec 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)

$ 831,00 USD totaal voor 3 nachten

23–26 nov 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 totaal voor 3 nachten

18–21 nov 2026

Private heated pool and spacious fenced backyard with artificial turf, colorful seating, and an outdoor dining area.

Bradenton Getaway | Pool & BBQ | Near the Island

Bradenton Getaway | Pool & BBQ | Near the Island

Bradenton Getaway | Pool & BBQ | Near the Island

Bradenton Getaway | Pool & BBQ | Near the Island

Bradenton Getaway | Pool & BBQ | Near the Island

3 bedrooms·2 baths

Bradenton • Florida

$ 1.258,00 USD totaal voor 3 nachten

18–21 nov 2026

Float the day away!

View from our lanai - straight on out!

The sweet life!

Condo with a View on Longboat Key

0 bedrooms·1 bath

Longboat Key • Florida

4.98(122 reviews)

$ 971,80 USD totaal voor 3 nachten

20–23 nov 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)

$ 971,80 USD totaal voor 3 nachten

18–21 nov 2026

Riverfront 4BR: Boat Dock, Heated Pool

Riverfront 4BR: Boat Dock, Heated Pool

Riverfront 4BR: Boat Dock, Heated Pool

Riverfront 4BR: Boat Dock, Heated Pool

Riverfront 4BR: Boat Dock, Heated Pool

Riverfront 4BR: Boat Dock, Heated Pool

4 bedrooms·4 baths

Ellenton • Florida

5(3 reviews)

$ 3.582,01 USD $ 3.264,24 USD totaal voor 5 nachten

11–16 dec 2026

Building Arial View

St Pete Beachside Condo

1 bedroom·1 bath

St. Pete Beach • Florida

5(3 reviews)

$ 1.297,68 USD totaal voor 5 nachten

18–23 nov 2026

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 totaal voor 3 nachten

18–21 nov 2026

Your favorite beach getaway (4)

Your favorite beach getaway (4)

Your favorite beach getaway (4)

Shared Laundry room located on 1st flooor

Your favorite beach getaway (4)

Your favorite beach getaway (4)

1 bedroom·1 bath

St. Pete Beach • Florida

5(3 reviews)

$ 1.606,00 USD totaal voor 6 nachten

18–24 nov 2026

Living room with Full Size sleep sofa

Private condo steps to beach (3)

Private condo steps to beach (3)

Newly remodeled bathroom as of 1/2024

Fully equipped kitchen

Private condo steps to beach (3)

1 bedroom·1 bath

St. Pete Beach • Florida

$ 1.511,70 USD totaal voor 6 nachten

18–24 nov 2026

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

4 bedrooms·3 baths

Bradenton • Florida

$ 1.693,00 USD totaal voor 3 nachten

22–25 nov 2026

Waterfront 3BR 2 1/2 Bath, Amazing View-Sunrises!

3 bedrooms·2½ baths

St. Pete Beach • Florida

5(3 reviews)

$ 13.750,00 USD totaal voor 30 nachten

1–31 jan 2027

*Close to Beach/Downtown*Heated Pool*Game Room* Fire Pit

*Close to Beach/Downtown*Heated Pool*Game Room* Fire Pit

*Close to Beach/Downtown*Heated Pool*Game Room* Fire Pit

Primary bedroom with king bed and a slider out to the covered pool area. There is also a full bathroom with walk in shower.

Kitchen with granite countertops and all new appliances. There is also a pass through window to the outdoor bar area

Close to Beach/DowntownHeated PoolGame Room Fire Pit

3 bedrooms·2 baths

Sarasota • Florida

$ 1.028,30 USD totaal voor 3 nachten

18–21 nov 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)

$ 1.430,60 USD $ 1.370,12 USD totaal voor 5 nachten

14–19 jan 2027