Hubbel Hideaway

4 bedrooms·3 baths
Bradenton • Florida

$1,693.00 USD total for 3 nights

Nov 22 – 25, 2026

Paradise Blu

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

$6,372.74 USD total for 7 nights

Dec 6 – 13, 2026

Luxe Island Escape

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

$6,396.12 USD total for 7 nights

Nov 27 – Dec 4, 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key

5 bedrooms·4 baths
Sarasota • Florida
5(4 reviews)

$10,481.85 USD $9,993.42 USD total for 7 nights

Dec 19 – 26, 2026

Anna Margaritas

2 bedrooms·2 baths
Anna Maria • Florida

$3,114.68 USD total for 7 nights

Dec 8 – 15, 2026

The Veranda on Jacaranda

4 bedrooms·3½ baths
Anna Maria • Florida

$4,315.99 USD total for 7 nights

Dec 4 – 11, 2026

The Lookout

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

$4,995.41 USD total for 7 nights

Nov 30 – Dec 7, 2026

Sun Soaked Paradise - Heated Pool

3 bedrooms·2 baths
Bradenton • Florida
5(3 reviews)

$980.00 USD total for 3 nights

Nov 19 – 22, 2026

Golf Course Condo

2 bedrooms·2 baths
Sarasota • Florida

$3,665.00 USD total for 30 nights

Nov 18 – Dec 18, 2026

Palmetto House

3 bedrooms·3 baths
Sarasota • Florida

$2,593.12 USD total for 7 nights

Nov 29 – Dec 6, 2026

Riverfront 4BR: Boat Dock, Heated Pool

4 bedrooms·4 baths
Ellenton • Florida
5(3 reviews)

$3,582.01 USD $3,264.24 USD total for 5 nights

Dec 11 – 16, 2026

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Gulf

2 bedrooms·1 bath
Sarasota • Florida
5(2 reviews)

$2,178.64 USD total for 7 nights

Nov 28 – Dec 5, 2026

Sarasota vacation rental

3 bedrooms·2 baths
Sarasota • Florida

$500.00 USD total for 3 nights

Nov 18 – 21, 2026

Tropi-Casa

4 bedrooms·2 baths
Bradenton • Florida

$862.50 USD total for 3 nights

Nov 18 – 21, 2026

Siesta Key Village Vacation Rental – Walk to Beach

2 bedrooms·1 bath
Sarasota • Florida

$745.76 USD total for 3 nights

Nov 29 – Dec 2, 2026

Treasure Boat

3 bedrooms·2 baths
Siesta Key • Florida

$1,065.75 USD total for 3 nights

Nov 28 – Dec 1, 2026

Village Canal home short walk to Beach with pool

3 bedrooms·2 baths
Siesta Key • Florida
5(26 reviews)

$14,950.00 USD total for 28 nights

Apr 15 – May 13, 2027

Commonwealth

4 bedrooms·3½ baths
Siesta Key • Florida

$1,496.25 USD total for 3 nights

Nov 30 – Dec 3, 2026

Siesta Key Home | Heated Pool, Theater & Arcade

4 bedrooms·3 baths
Siesta Key • Florida
5(36 reviews)

$3,701.06 USD total for 3 nights

Nov 18 – 21, 2026

The Funky Fish House

2 bedrooms·2 baths
Sarasota • Florida
4.99(156 reviews)

$1,375.73 USD total for 5 nights

Nov 27 – Dec 2, 2026

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

Dec 1 – 4, 2026

#1 Siesta Key Beach Glass House w/supplies

2 bedrooms·2 baths
Siesta Key • Florida
4.64(58 reviews)

$2,141.35 USD total for 7 nights

Nov 21 – 28, 2026

Cozy Room 5 miles from beaches!

1 bedroom·1 bath
Sarasota • Florida
4.95(75 reviews)

$225.00 USD total for 3 nights

Nov 18 – 21, 2026

Blanca Cottage| Private 2BR Pool Home Near Siesta

2 bedrooms·2 baths
Siesta Key • Florida
5(4 reviews)

$5,391.20 USD total for 7 nights

Dec 7 – 14, 2026