Huge pool with attached spa
Welcome to Paradise Blu!
Huge tropical yard and pool
Grand living room with views

Paradise Blu

4 bedrooms·4½ baths
Anna Maria • Florida
5(2 reviews)

$ 6.372,74 USD totaal voor 7 nachten

6–13 dec 2026

Secluded backyard
Private saltwater pool
So close to the beach!
Bliss by the Beach- Beach Boutique Rentals
Beautiful and open kitchen

Bliss by the Beach

2 bedrooms·2 baths
Anna Maria • Florida

$ 3.787,95 USD totaal voor 5 nachten

5–10 jun 2027

Welcome to Luxe Island Escape
Multi-level decks overlooking the pool
Main foyer
Amazing views from every room

Luxe Island Escape

4 bedrooms·4½ baths
Anna Maria • Florida
5(1 review)

$ 6.396,12 USD totaal voor 7 nachten

27 nov – 4 dec 2026

Sunny Limelight pool
See how close you are to the beach
Welcome to Limelight!
Bright open living space

Limelight

3 bedrooms·2 baths
Anna Maria • Florida

$ 3.439,62 USD totaal voor 7 nachten

4–11 dec 2026

Blissful pool and spa
Huge backyard paradise
Welcome to adorable Anna Margaritas
Come on in!
Welcoming open floor plan

Anna Margaritas

2 bedrooms·2 baths
Anna Maria • Florida

$ 3.114,68 USD totaal voor 7 nachten

8–15 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

$ 3.719,02 USD totaal voor 7 nachten

29 nov – 6 dec 2026

Where the view becomes your backdrop
Your waterfront pool retreat awaits
Welcome to The Lookout
Your beach escape begins inside

The Lookout

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

$ 4.995,41 USD totaal voor 7 nachten

30 nov – 7 dec 2026

Resort-style backyard retreat
Welcome to the Veranda on Jacaranda
Tropical vacation begins here
Welcome to beach paradise

The Veranda on Jacaranda

4 bedrooms·3½ baths
Anna Maria • Florida

$ 4.315,99 USD totaal voor 7 nachten

4–11 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

18 nov – 16 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

$ 3.989,81 USD totaal voor 7 nachten

30 nov – 7 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

$ 13.625,00 USD totaal voor 30 nachten

18 nov – 18 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

$ 3.805,18 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)

$ 2.453,71 USD totaal voor 7 nachten

25 nov – 2 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

$ 3.963,96 USD totaal voor 7 nachten

28 nov – 5 dec 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

$ 2.390,94 USD totaal voor 7 nachten

1–8 dec 2026

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

Peaceful Holmes

3 bedrooms·3 baths
Holmes Beach • Florida

$ 2.985,44 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

$ 2.450,02 USD totaal voor 7 nachten

28 nov – 5 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

$ 14.927,14 USD totaal voor 30 nachten

18 nov – 18 dec 2026

Soak up the sun!
Dine outside by the pool
Private right side of the duplex
Entryway
Charming coastal decor

Gone Coastal

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

$ 1.812,44 USD totaal voor 7 nachten

18–25 nov 2026

The entire complex is yours!
Gate opens in between the 2 sides
Both sides of the duplex included
First of 2 separate living rooms
All new furniture

Gone Coastal Duplex

4 bedrooms·4 baths
Holmes Beach • Florida

$ 3.842,11 USD totaal voor 7 nachten

23–30 nov 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

$ 2.042,61 USD totaal voor 7 nachten

23–30 nov 2026

Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA
Beachfront Condo on Anna Maria Island, FL, USA

Beachfront Condo on Anna Maria Island, FL, USA

2 bedrooms·2 baths
Anna Maria • Florida

$ 3.875,00 USD totaal voor 14 nachten

18 nov – 2 dec 2026