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

5.359,75 $ USD gesamt für 7 Nächte

16.–23. Nov. 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 gesamt für 7 Nächte

7.–14. Nov. 2026

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

No Tan Lines

4 bedrooms·4 baths
Anna Maria • Florida

11.011,81 $ USD gesamt für 7 Nächte

11.–18. Dez. 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

3.269,76 $ USD gesamt für 7 Nächte

8.–15. 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)

3.768,69 $ USD gesamt für 7 Nächte

11.–18. 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

3.554,09 $ USD gesamt für 7 Nächte

5.–12. Dez. 2026

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

Paradise Pointe

3 bedrooms·2 baths
Anna Maria • Florida

3.331,31 $ USD gesamt für 7 Nächte

11.–18. Nov. 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

3.067,90 $ USD gesamt für 7 Nächte

12.–19. 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 gesamt für 5 Nächte

5.–10. Juni 2027

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)

3.096,21 $ USD gesamt für 7 Nächte

10.–17. Nov. 2026

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)

3.580,18 $ USD gesamt für 4 Nächte

1.–5. Dez. 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 gesamt für 7 Nächte

29. Nov. – 6. Dez. 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 gesamt für 4 Nächte

8.–12. Mai 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

3.384,23 $ USD gesamt für 7 Nächte

7.–14. Nov. 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

3.360,85 $ USD gesamt für 7 Nächte

14.–21. Nov. 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

3.280,84 $ USD gesamt für 7 Nächte

29. Nov. – 6. Dez. 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

Sand Trap

4 bedrooms·4 baths
Anna Maria • Florida

6.323,50 $ USD gesamt für 7 Nächte

18.–25. Jan. 2027

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

7 bedrooms·4 baths
Tampa • Florida

3.612,00 $ USD gesamt für 3 Nächte

7.–10. Nov. 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

3.517,16 $ USD gesamt für 7 Nächte

30. Nov. – 7. Dez. 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

3.572,55 $ USD gesamt für 7 Nächte

10.–17. 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

3.012,52 $ USD gesamt für 7 Nächte

7.–14. Nov. 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

8.680,58 $ USD gesamt für 7 Nächte

13.–20. Nov. 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 – $609/ Nacht(zzgl. Gebühren & Steuern)
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

3.337,46 $ USD gesamt für 7 Nächte

1.–8. Dez. 2026