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

$ 6.301,35 USD totaal voor 7 nachten

18–25 jan 2027

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

$ 3.519,63 USD totaal voor 7 nachten

30 nov – 7 dec 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

$ 3.498,70 USD totaal voor 7 nachten

15–22 nov 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

$ 3.822,41 USD totaal voor 7 nachten

7–14 dec 2026

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 totaal voor 7 nachten

29 nov – 6 dec 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 – $620/ nacht(excl. kosten & belastingen)
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

$ 3.338,69 USD totaal voor 7 nachten

1–8 dec 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

$ 6.520,44 USD totaal voor 7 nachten

28 nov – 5 dec 2026

Front of Home
Front door to unit
Entrance Stairs
Kitchen
Closet in Kitchen area

The Blue House in Clearwater

2 bedrooms·1 bath
Clearwater • Florida

$ 3.559,50 USD totaal voor 30 nachten

15 nov – 15 dec 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

$ 13.700,00 USD totaal voor 30 nachten

15 nov – 15 dec 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 totaal voor 28 nachten

15 nov – 13 dec 2026

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

Ocean Minded

3 bedrooms·3 baths
Anna Maria • Florida

$ 3.954,12 USD totaal voor 7 nachten

29 nov – 6 dec 2026

Gulf Breeze Getaway - Sand Key image 1
Gulf Breeze Getaway - Sand Key image 2
Gulf Breeze Getaway - Sand Key image 3
Gulf Breeze Getaway - Sand Key image 4
Gulf Breeze Getaway - Sand Key image 5

Gulf Breeze Getaway - Sand Key

2 bedrooms·2 baths
Clearwater • Florida

$ 5.650,00 USD totaal voor 30 nachten

15 nov – 15 dec 2026

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

$ 4.201,52 USD totaal voor 7 nachten

30 nov – 7 dec 2026

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

$ 3.812,57 USD totaal voor 7 nachten

2–9 jan 2027

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)

$ 2.653,11 USD totaal voor 7 nachten

21–28 nov 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

$ 3.596,24 USD totaal voor 7 nachten

28 nov – 5 dec 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

$ 2.440,17 USD totaal voor 7 nachten

1–8 dec 2026

Spectacular sunsets await
Welcome to Blue Tides
Your retreat awaits
Coastal comfort meets modern style
A living space made for gathering

Blue Tides

3 bedrooms·3 baths
Holmes Beach • Florida

$ 15.757,97 USD totaal voor 30 nachten

15 nov – 15 dec 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

$ 3.872,88 USD totaal voor 7 nachten

28 nov – 5 dec 2026

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

$ 3.040,83 USD totaal voor 7 nachten

28 nov – 5 dec 2026

Cocktails and Dreams
Welcome to Cocktails and Dreams
Beautiful single story home
Cocktails and Dreams
Gather around for movie night

Cocktails and Dreams

4 bedrooms·4 baths
Holmes Beach • Florida

$ 7.750,06 USD totaal voor 7 nachten

3–10 apr 2027

Beautiful backyard with pool and tiki bar
Poolside tiki bar
Ground level home
Beautiful ground level beachhouse
Huge dining room table

Gone Coastal 3

3 bedrooms·2½ baths
Holmes Beach • Florida

$ 2.480,79 USD totaal voor 7 nachten

28 nov – 5 dec 2026

Welcome to Gone Coastal Too!
Dine outside by the pool
Private left side of the duplex
All new furniture
Charming coastal decor

Gone Coastal, Too

2 bedrooms·2 baths
Holmes Beach • Florida

$ 2.089,38 USD totaal voor 7 nachten

23–30 nov 2026