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)

$1,780.00 USD total for 3 nights

Feb 23 – 26, 2027

Stunning nighttime landscape
Soak up the sun in your own backyard oasis
Amazing location in Holmes Beach

Peaceful Holmes

3 bedrooms·3 baths
Holmes Beach • Florida

$2,933.74 USD total for 7 nights

Nov 11 – 18, 2026

Beautiful tropical pool
Welcome to Wish Upon a Starfish!
Plenty of living room seating
Dining area and kitchen
Cozy dining area

Wish Upon a Starfish

3 bedrooms·3 baths
Holmes Beach • Florida

$2,046.30 USD total for 7 nights

Nov 9 – 16, 2026

Coastal Palm Hideaway
Coastal Palm Hideaway
Coastal Palm Hideaway
Coastal Palm Hideaway
Coastal Palm Hideaway

Coastal Palm Hideaway

4 bedrooms·2 baths
Bradenton • Florida
4.92(62 reviews)

$794.39 USD total for 3 nights

Dec 7 – 10, 2026

Welcome to Bubbles Up
Sprawling 4 bedroom home
Adorable entry awaits
Grand open living space
Gather together with the family

Bubbles Up

4 bedrooms·3½ baths
Holmes Beach • Florida

$3,917.19 USD total for 7 nights

Nov 28 – Dec 5, 2026

Welcome to A Lazy River Day & Night
Day and Night
Open Kitchen, Dining, Living Area Day Side
Day Side New Kitchen, Dining Area with added Food Pantry and Complimentary Beverage Center

A Lazy River - Both Units

4 bedrooms·3½ baths
Holmes Beach • Florida

$3,794.48 USD total for 7 nights

Nov 14 – 21, 2026

The Pink Chicken private pool
Relax around the cocktail table
Welcome to the Pink Chicken
Private entrance with electronic lock

The Pink Chicken

3 bedrooms·2 baths
Holmes Beach • Florida
5(1 review)

$3,290.69 USD total for 7 nights

Nov 21 – 28, 2026

Lush and tropical!
Welcome to Silver Sands on Longboat Key!
Stroll north or south on the beach or just sit and wait for the sunrise or sunset -- you've got time.
Silver Sands Gulf Beach Resort!
White sandy beach - ideal!

Tropical Beach Condo!

1 bedroom·1 bath
Longboat Key • Florida
5(11 reviews)
$250/ night(excl. fees & taxes)
Welcome to AMI Beach Hideaway
Indoor/outdoor living at its finest
Elevated island retreat
Step inside this charming home
Welcoming coastal dining space

AMI Beach Hideaway

2 bedrooms·2 baths
Anna Maria • Florida

$3,327.61 USD total for 7 nights

Dec 14 – 21, 2026

Salt Therapy Beach Cottage 500 steps to the beach image 1
Salt Therapy Beach Cottage 500 steps to the beach image 2
Salt Therapy Beach Cottage 500 steps to the beach image 6
Salt Therapy Beach Cottage 500 steps to the beach image 3
Salt Therapy Beach Cottage 500 steps to the beach image 13

Salt Therapy Beach Cottage 500 steps to the beach

2 bedrooms·2 baths
Holmes Beach • Florida
$235 – $375/ night(excl. fees & taxes)
Bird's eye view
Stunning backyard with lazy river pool
Beautiful backyard
High end kitchen
Seating for 7 at the kitchen island

H2O Bungalow

3 bedrooms·3 baths
Anna Maria • Florida

$4,186.75 USD total for 7 nights

Nov 30 – Dec 7, 2026

Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool
Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

3 bedrooms·3 baths
Holmes Beach • Florida
5(9 reviews)

$15,424.71 USD total for 28 nights

Nov 9 – Dec 7, 2026

Pool area designed for relaxing and entertaining
Quiet island street just a short walk to the beach
Ultimate relaxation

Ocean Minded

3 bedrooms·3 baths
Anna Maria • Florida

$3,946.73 USD total for 7 nights

Nov 29 – Dec 6, 2026

Guests love the outdoor space of this home, which includes a heated pool, covered seating area with a Roku TV, outdoor dining space and mural. Everything is screened so bugs and tropical wildl
The home has a large heated pool, with new paver deck and new pool cage!
The garage of the home has foosball, darts, and a pingpong table. There are beach chairs, toys, and umbrellas available for guests to use.
Enjoy a movie night after a day at the beach! The living room has a large cozy sectional, tv, and fireplace.
The primary bedroom flows right out to the pool!

Palma Rosa

3 bedrooms·2 baths
Bradenton • Florida
5(41 reviews)

$1,073.57 USD total for 3 nights

Nov 13 – 16, 2026

Relax and unwind in the covered seating area next to the pool, with comfortable outdoor furniture and a dining table
The incredible outdoor space truly sets this home apart.The new saltwater pool with a spa and sunshelf were completed in spring 2023.
Guests love that the living room flows directly out to the pool and lanai!
The kitchen includes a backsplash made of real shells, floating driftwood shelves made by a local artist, granite countertops, and all the appliances and accessories you will need.
The primary bedroom has a king bed, armoire and dresser for clothing storage, and direct access to the swimming pool.

Palma Janoli

3 bedrooms·2 baths
Bradenton • Florida
5(110 reviews)

$1,083.76 USD total for 3 nights

Dec 1 – 4, 2026

Palma Rosa and Palma Janoli
The incredible outdoor space truly sets this home apart.The new saltwater pool with a spa and sunshelf were completed in spring 2023.
Palma Rosa's outdoor space includes a covered outdoor seating/dining area with an outdoor TV
Easily walk between the two houses.
Relax and unwind in the covered seating area next to the pool, with comfortable outdoor furniture and a dining table

Palma Rosa and Palma Janoli

6 bedrooms·4 baths
Bradenton • Florida

$5,909.16 USD total for 3 nights

Dec 26 – 29, 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

$3,332.54 USD total for 7 nights

Dec 1 – 8, 2026

Gulf Coast Home w/Private Pool Near AMI & Beaches
Gulf Coast Home w/Private Pool Near AMI & Beaches
Gulf Coast Home w/Private Pool Near AMI & Beaches
Gulf Coast Home w/Private Pool Near AMI & Beaches
Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

4 bedrooms·3 baths
Bradenton • Florida
5(22 reviews)

$3,355.52 USD total for 5 nights

Nov 9 – 14, 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

$6,305.04 USD total for 7 nights

Nov 28 – Dec 5, 2026

Kitchen
Aerial
Guest Bedroom converted to a king bed
Beach Access
Living Area

Sea Club III #4 2B / 2B Direct Beachfront Condo by RVA

2 bedrooms·2 baths
Longboat Key • Florida

$1,820.00 USD total for 5 nights

Nov 9 – 14, 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)

$994.40 USD total for 3 nights

Nov 9 – 12, 2026

Relax by the fire pit and enjoy sunset views in this private backyard
The Salty Palm
Let the kids play putt putt golf, bocce ball and more while you relax in the refreshing pool. Summertime paradise awaits!
The Salty Palm
The Salty Palm

The Salty Palm

3 bedrooms·2 baths
Bradenton • Florida
5(43 reviews)

$1,052.56 USD total for 3 nights

Nov 9 – 12, 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

$3,011.28 USD total for 7 nights

Nov 9 – 16, 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
$185 – $609/ night(excl. fees & taxes)