Featured
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)

$6,302.00 USD total for 30 nights

Nov 17 – Dec 17, 2026

Take a dip to cool off
Your luxury vacation awaits
Bright hallway with curated island décor
Coastal curb appeal meets modern luxury

Sun and Spring

3 bedrooms·2½ baths
Anna Maria • Florida

$3,956.58 USD total for 7 nights

Nov 27 – Dec 4, 2026

Beautiful heated pool
Welcome to Sea Mist!
Perfect location steps to the Bay Beach
Bright and welcoming
Thoughtfully designed for gathering

Sea Mist

3 bedrooms·2 baths
Anna Maria • Florida

$3,455.62 USD total for 7 nights

Nov 30 – Dec 7, 2026

Loungers by the pool
Beautiful backyard with pool, hot tub and loungers
Welcome to My Mistress!
Entry way

My Mistress

3 bedrooms·3 baths
Anna Maria • Florida

$3,828.57 USD total for 7 nights

Dec 7 – 14, 2026

Relaxing saltwater pool area ideal for all-day lounging
Resort-style saltwater pool perfect for cooling off
Inviting retreat with room for friends and family to relax
Welcome to Manatee Manor

Manatee Manor

3 bedrooms·2 baths
Anna Maria • Florida

$3,433.47 USD total for 7 nights

Nov 28 – Dec 5, 2026

This is what backyard fun looks like!
No houses between you and the water
Modern, elevated home
Right across the street from the Bay beach
Welcome to Sand Trap!

Sand Trap

4 bedrooms·4 baths
Anna Maria • Florida

$6,328.43 USD total for 7 nights

Jan 18 – 25, 2027

Stunning modern beach retreat
Oversized heated L-shaped pool
Welcome to Jungalow Beach
Step into paradise
Open-air lanai by the pool

Jungalow Beach

4 bedrooms·6½ baths
Anna Maria • Florida

$8,742.12 USD total for 7 nights

Nov 29 – Dec 6, 2026

Welcome to Beach Don't Kill My Vibe
Welcoming foyer and window seat
Prime location just off Pine Avenue
Super close to the beach!
Comfortable sectional in the living room

Beach Don't Kill My Vibe

2 bedrooms·1 bath
Anna Maria • Florida
$175 – $620/ night(excl. fees & taxes)
Your own private slice of island calm
Sparkling pool steps from the water
Welcome to Anna Belle
Step inside to light, warmth, and modern coastal style
Open, airy entry that sets the tone for your stay

Anna Belle

3 bedrooms·3 baths
Anna Maria • Florida
5(1 review)

$4,611.39 USD total for 7 nights

Nov 29 – Dec 6, 2026

Heated private pool
Welcome to Hook Wine and Sinker
Spacious elevated 4 bedroom home
Welcome inside

Hook Wine and Sinker

4 bedrooms·2½ baths
Anna Maria • Florida
5(2 reviews)

$3,955.35 USD total for 7 nights

Dec 2 – 9, 2026

Swim, splash, or float the day away
Laid-back living along the canal
Welcome to H2O 360
Your coastal getaway begins here
Open living space filled with light

H2O 360

3 bedrooms·2 baths
Anna Maria • Florida

$3,285.76 USD total for 7 nights

Dec 1 – 8, 2026

Canalfront paradise awaits
Private tropical backyard oasis
Welcome to Iris-istible Options
Your coastal escape begins here

Iris-istible Options

4 bedrooms·3 baths
Anna Maria • Florida

$3,955.35 USD total for 7 nights

Nov 28 – Dec 5, 2026

Beautiful private backyard with pool
Sparkling private heated pool
Welcome to Idyll Tides!
Short walk to Bean Point

Idyll Tides

3 bedrooms·2 baths
Anna Maria • Florida

$3,177.45 USD total for 7 nights

Nov 29 – Dec 6, 2026

Enjoy your waterfront pool and spa
Direct beachfront home - No Tan Lines
Elevated beachfront home with pool
Welcome to No Tan Lines!

No Tan Lines

4 bedrooms·4 baths
Anna Maria • Florida

$11,011.81 USD total for 7 nights

Dec 11 – 18, 2026

Drift into island relaxation by the water
Blue-water bliss with swaying palms above
Dip your toes while you unwind in style
Welcome to Jungalow Bay

Jungalow Bay

3 bedrooms·3 baths
Anna Maria • Florida
5(1 review)

$3,659.35 USD total for 7 nights

Nov 17 – 24, 2026

Sunset soaks await
Welcome to Casa Azul
Modern island charm awaits
Bright coastal comfort
Relaxation starts here

Casa Azul

4 bedrooms·4½ baths
Anna Maria • Florida

$6,067.49 USD total for 7 nights

Nov 28 – Dec 5, 2026

Private heated pool
Whispering Winds by Beach Boutique Rentals
Steps to the Bay!
Stylish living area
Full of character and charm!

Whispering Winds

2 bedrooms·2 baths
Anna Maria • Florida
5(5 reviews)

$2,895.58 USD total for 7 nights

Nov 17 – 24, 2026

A pool unlike any other
Fun beyond the beach awaits
Welcome to Beachfront Bliss
Welcome to unforgettable island living
Open living area made for gathering

Beachfront Bliss

5 bedrooms·5½ baths
Anna Maria • Florida

$11,811.86 USD total for 7 nights

Nov 28 – Dec 5, 2026

Welcome to Paradise
Private tropical oasis
Convenient ground level home
Charming beach house

Paradise Pointe

3 bedrooms·2 baths
Anna Maria • Florida

$3,433.47 USD total for 7 nights

Nov 28 – Dec 5, 2026

White Palms gorgeous pool
Welcome to White Palms
Ground level north end home!
Welcoming entryway
Adorable details

White Palms

3 bedrooms·2 baths
Anna Maria • Florida

$3,614.40 USD total for 7 nights

Dec 6 – 13, 2026

Experience luxury!
Beautiful backyard at any time of the day
Amazing views from the top deck
Almost bay front location

Pier to Pier Paradise

4 bedrooms·4½ baths
Anna Maria • Florida

$4,857.56 USD total for 7 nights

Nov 17 – 24, 2026

Beautiful huge saltwater pool
Jacaranda Gem
So close to the beach
Newly remodeled coastal home
Dining area with a view!

Jacaranda Gem

3 bedrooms·2½ baths
Anna Maria • Florida
5(1 review)

$4,095.66 USD total for 4 nights

May 8 – 12, 2027

Refreshing dips under open skies
Game room by the pool
Welcome to Pelican Place
Bright and welcoming island retreat

Pelican Place

3 bedrooms·2 baths
Anna Maria • Florida

$3,557.78 USD total for 7 nights

Dec 5 – 12, 2026

Poolside backyard retreat
Kick back and relax poolside
Welcome to Bay Bungalow
Step inside the open living space
Recently updated interior with new furniture

Bay Bungalow

3 bedrooms·2 baths
Anna Maria • Florida

$2,976.82 USD total for 7 nights

Nov 29 – Dec 6, 2026