Location

Dates

Guests

Vacation rentals in Anna Maria, Florida, United States

The Bayou Breeze Cottage

The Bayou Breeze Cottage

The Bayou Breeze Cottage

The Bayou Breeze Cottage

The Bayou Breeze Cottage

The Bayou Breeze Cottage

1 bedroom·1 bath

St. Petersburg • Florida

5(28 reviews)

$417.87 USD $350.30 USD total for 3 nights

Oct 6 – 9, 2026

Comfortable sleeper sofa for guests while immersed in the tranquil ocean vibe!

Wonderful open space living area to relax and watch your favorite game or a good movie!

Have a picnic right on the water with the breathtaking view!

Enjoy your morning coffee and breakfast at the open concept dining area.

The bay beach in the community is a day of fun and sun!

Bahia Beach Calm Ruskin Retreat

2 bedrooms·1½ baths

Ruskin • Florida

$617.15 USD total for 3 nights

Sep 28 – Oct 1, 2026

Welcome to your private paradise just minutes from the beach—where relaxation begins the moment you pull in.

Big group? No problem. Our extendable dining table fits up to 10—perfect for family feasts, card nights, or celebratory toasts.

Get the best of both worlds: soft and firm pillows, a private ensuite, blackout blinds for restful sleep, and a king bed made for unwinding. Plus, a smart TV for ultimate relaxation.

When the beach is a few blocks away but the pool is right here. Welcome to the best of both worlds.

Skip the restaurants (if you want to). This kitchen’s got everything: oven, microwave, fridge, dishwasher—even a TV so you don’t miss a moment.

Siesta Key Home | Heated Pool, Theater & Arcade

4 bedrooms·3 baths

Siesta Key • Florida

5(36 reviews)

$3,195.95 USD total for 3 nights

Sep 28 – Oct 1, 2026

The Parkside Retreat at 78th Street

3 bedrooms·2 baths

Pinellas Park • Florida

$114 – $250/ night(excl. fees & taxes)

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 1

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 2

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 3

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 4

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 5

Lovely room 5 miles from Siesta Key w/ Pool & Spa!

1 bedroom·1 bath

Sarasota • Florida

4.87(60 reviews)

$225.00 USD total for 3 nights

Oct 4 – 7, 2026

Cozy Room 5 miles from beaches! image 1

Cozy Room 5 miles from beaches! image 2

Cozy Room 5 miles from beaches! image 3

Cozy Room 5 miles from beaches! image 4

Cozy Room 5 miles from beaches! image 5

Cozy Room 5 miles from beaches!

1 bedroom·1 bath

Sarasota • Florida

4.95(75 reviews)

$225.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

Beautiful details that set this home apart. Oceanfront Luxury home.

Ocean Front with 180 degree views inside the home of the ocean

The most epic sunsets you have ever seen!

Master #1 - King Bed ( There are two of these rooms mirrored on each side of the house)

OceanfrontVilla/Pool/HotTub/8bedroom

8 bedrooms·6 baths

Redington Shores • Florida

5(4 reviews)

$4,927.26 USD total for 3 nights

Sep 28 – Oct 1, 2026

you never have to cover the windows, it's a private yard.

Pool view from the dining area

TOP WORLD BEACH AND #1 US BEACH

my favorite yellow lifeguard shack. LET'S GO VISIT>>>>> Are you coming????

#1 Siesta Key Beach Glass House w/supplies

2 bedrooms·2 baths

Siesta Key • Florida

4.64(58 reviews)

$2,062.25 USD total for 7 nights

Oct 3 – 10, 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Blanca Cottage| Private 2BR Pool Home Near Siesta

2 bedrooms·2 baths

Siesta Key • Florida

5(2 reviews)

$13,392.70 USD total for 14 nights

Dec 12 – 26, 2026

Pond-side ART-home with private pool. DOGS WELCOME

5 bedrooms·3 baths

Pinellas Park • Florida

5(20 reviews)

$318/ night(excl. fees & taxes)

Relaxed lounge area, kick back, stream, and recharge.

Open living space designed for comfort, light, and flow.

Inviting dining space with subtle coastal tones for shared meals and relaxed evenings.

Fully equipped kitchen, perfect for easy meals or longer stays.

Modern kitchen with clean lines and coastal-inspired finishes.

The Indigo Escape

2 bedrooms·2 baths

Sarasota • Florida

$6,757.67 USD total for 14 nights

Sep 28 – Oct 12, 2026

The Sapphire Escape

The Sapphire Escape

The Sapphire Escape

The Sapphire Escape

The Sapphire Escape

The Sapphire Escape

1 bedroom·1 bath

Sarasota • Florida

$2,053.91 USD total for 14 nights

Oct 21 – Nov 4, 2026

2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 bedrooms·2 baths

Sarasota • Florida

$100/ night(excl. fees & taxes)

Spotless & Tranquil Bungalow (Allergen Friendly)

Ra the Tortoise, he loves cucumbers so bring some snackies!

Spotless & Tranquil Bungalow (Allergen Friendly)

Spotless & Tranquil Bungalow (Allergen Friendly)

Spotless & Tranquil Bungalow (Allergen Friendly)

Spotless & Tranquil Bungalow (Allergen Friendly)

1 bedroom·1 bath

Parrish • Florida

5(82 reviews)

$718.80 USD total for 3 nights

Jan 4 – 7, 2027

Casa mar - Unit 74

Casa mar - Unit 74

Casa mar - Unit 74

Casa mar - Unit 74

Casa mar - Unit 74

Casa mar - Unit 74

1 bedroom·1 bath

Siesta Key • Florida

$873.20 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casa Mar - Unit 4 1 Bedroom 1 Bath

Casa Mar - Unit 4 1 Bedroom 1 Bath

Casa Mar - Unit 4 1 Bedroom 1 Bath

Casa Mar - Unit 4 1 Bedroom 1 Bath

Casa Mar - Unit 4 1 Bedroom 1 Bath

Casa Mar - Unit 4 1 Bedroom 1 Bath

1 bedroom·1 bath

Siesta Key • Florida

$941.60 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

1 bedroom·1 bath

Siesta Key • Florida

$941.60 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

1 bedroom·1 bath

Siesta Key • Florida

$941.60 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side

Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side

Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side

Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side

Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side

Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side

2 bedrooms·2 baths

Siesta Key • Florida

Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View

Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View

Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View

Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View

Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View

Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View

2 bedrooms·2 baths

Siesta Key • Florida

$1,254.40 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casa Mar Unit 34 | 2BR Steps to Beach

Casa Mar Unit 34 | 2BR Steps to Beach

Casa Mar Unit 34 | 2BR Steps to Beach

Casa Mar Unit 34 | 2BR Steps to Beach

Casa Mar Unit 34 | 2BR Steps to Beach

Casa Mar Unit 34 | 2BR Steps to Beach

2 bedrooms·2 baths

Siesta Key • Florida

$1,254.40 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front

2 bedrooms·2 baths

Siesta Key • Florida

$1,560.40 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front

2 bedrooms·2 baths

Siesta Key • Florida

$1,560.40 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front

2 bedrooms·2 baths

Siesta Key • Florida

$1,560.40 USD total for 3 nights

Sep 28 – Oct 1, 2026