Welcome to your home away from home!
This large pool and spacious patio will make it hard to decide if you want to go to the beach or stay in.
Renovated inside and out!
Double sinks, soaker tub and walk in shower!
This brand new kitchen is stocked with everything you need for your meals in!

Twin Oaks Retreat

5 bedrooms·3 baths
Clearwater • Florida

$ 1.135,58 USD $ 1.051,39 USD totaal voor 3 nachten

15–18 nov 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

$ 3.112,21 USD totaal voor 7 nachten

8–15 dec 2026

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

The Veranda on Jacaranda

4 bedrooms·3½ baths
Anna Maria • Florida

$ 4.317,22 USD totaal voor 7 nachten

4–11 dec 2026

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)

$ 5.842,24 USD totaal voor 7 nachten

15–22 nov 2026

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)

$ 6.367,81 USD totaal voor 7 nachten

6–13 dec 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

$ 11.134,89 USD totaal voor 7 nachten

15–22 nov 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

$ 3.049,44 USD totaal voor 7 nachten

29 nov – 6 dec 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

$ 4.796,02 USD totaal voor 7 nachten

16–23 nov 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 totaal voor 7 nachten

11–18 dec 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)

$ 2.920,20 USD totaal voor 7 nachten

15–22 nov 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 totaal voor 7 nachten

6–13 dec 2026

Your private pool, heated year-round to 80°F and ready for fall swims. Sun loungers and an umbrella line the deck, and the fully fenced backyard keeps the fun contained.
Red Adirondack chairs circle the fire pit under café lights. Fall evenings in Clearwater were made for slow talks and s'mores.
The whole backyard in one frame: heated pool, lounge chairs and cornhole on the lawn. Kids play, grown-ups relax, all inside a fenced yard.
Open-concept living made for your whole crew: a colorful mural, big sectional and dining table in one bright space, so nobody is stuck in another room while dinner comes together.
King primary suite with green and gold accents, a smart TV and ceiling fan. Your own retreat at the end of the day.

Heated pool, fire pit, games · dog friendly

3 bedrooms·2 baths
Clearwater • Florida

$ 945,06 USD totaal voor 3 nachten

15–18 nov 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)

$ 3.666,19 USD totaal voor 7 nachten

15–22 nov 2026

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

$ 3.555,32 USD totaal voor 7 nachten

5–12 dec 2026

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

Paradise Pointe

3 bedrooms·2 baths
Anna Maria • Florida

$ 3.496,24 USD totaal voor 7 nachten

28 nov – 5 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

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)

$ 3.013,75 USD totaal voor 7 nachten

15–22 nov 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

Stunning Gulf Views, Elevator to All Floors, Mini Golf, Heated Pool/Spa
Fun in the sun starts here - Hosted by RentAnnaMaria
Sunset Views from Shore to Please! - Hosted by RentAnnaMaria
Shore to Please - Hosted by RentAnnaMaria
Amazing Views! Main Living Space (3rd Floor) - Elevator to All Floors - Hosted by RentAnna Maria

Shore to Please

5 bedrooms·4½ baths
Anna Maria • Florida
5(13 reviews)

$ 3.011,59 USD totaal voor 4 nachten

6–10 dec 2026

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 totaal voor 7 nachten

29 nov – 6 dec 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 totaal voor 4 nachten

8–12 mei 2027

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

$ 4.306,14 USD totaal voor 7 nachten

28 nov – 5 dec 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

$ 3.496,24 USD totaal voor 7 nachten

28 nov – 5 dec 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

$ 3.273,46 USD totaal voor 7 nachten

29 nov – 6 dec 2026