Location

Dates

Guests

Vacation rentals in Anna Maria, Florida, United States

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

1 bedroom·1 bath

Seminole • Florida

$568.96 USD total for 3 nights

Nov 18 – 21, 2026

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths

Sarasota • Florida

$150/ night(excl. fees & taxes)

Sun Haven House - 4 mi to beach! 2 beds/2 baths image 1

Well equipped kitchen with full size appliances including a dishwasher.

King Size Bed; Nectar mattress, light cotton blanket along with linens

Queen size Nectar mattress in master bedroom with walk-in closet and adjoining bathroom with large shower.

Cozy mood lighting to enjoy tropical nights and conversation with a cool drink or two.

Sun Haven House - 4 mi to beach! 2 beds/2 baths

2 bedrooms·2 baths

Sarasota • Florida

$4,040.59 USD total for 30 nights

Nov 18 – Dec 18, 2026

Private Beach Access, Gorgeous Partial Views image 1

Private Beach Access, Gorgeous Partial Views image 2

Private Beach Access, Gorgeous Partial Views image 3

Private Beach Access, Gorgeous Partial Views image 4

Private Beach Access, Gorgeous Partial Views image 5

Private Beach Access, Gorgeous Partial Views

2 bedrooms·2 baths

Indian Shores • Florida

4.89(19 reviews)

$1,329.30 USD total for 3 nights

Nov 18 – 21, 2026

Siesta Dunes Pool

Living room - 65" TV, sleeper sofa

Lanai with sliders - "Palm View"

Living room - 65" TV, sleeper sofa

Living room with 65" TV

Palm View at Siesta Dunes

2 bedrooms·2 baths

Siesta Key • Florida

5(15 reviews)

$2,580.08 USD total for 7 nights

Nov 28 – Dec 5, 2026

Back yard with new pool 15x28 ft

Pool Depth 3ft-5ft

Casa Blanca Ranch Home near Siesta Key Beach

15x28 ft pool with spa/hot tub

New Sun Shelves with pool chaises

Casa Blanca Ranch Home near Siesta Key Beach

3 bedrooms·2 baths

Sarasota • Florida

5(18 reviews)

$2,264.65 USD total for 5 nights

Nov 18 – 23, 2026

10 Min to Beach-King bed, fenced yard, cozy charm image 1

10 Min to Beach-King bed, fenced yard, cozy charm image 2

Propane fire pit for quick and easy fire ambiance

10 Min to Beach-King bed, fenced yard, cozy charm image 4

10 Min to Beach-King bed, fenced yard, cozy charm image 5

10 Min to Beach-King bed, fenced yard, cozy charm

3 bedrooms·1 bath

Seminole • Florida

4.78(9 reviews)

$575.00 USD total for 3 nights

Nov 18 – 21, 2026

5 min walk to the best Beach in America! image 1

5 min walk to the best Beach in America! image 2

5 min walk to the best Beach in America! image 3

5 min walk to the best Beach in America! image 4

5 min walk to the best Beach in America! image 5

5 min walk to the best Beach in America!

1 bedroom·2 baths

Siesta Key • Florida

$3,120.00 USD $2,823.00 USD total for 30 nights

Nov 18 – Dec 18, 2026

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

2 bedrooms·2 baths

Sarasota • Florida

$722.00 USD total for 3 nights

Nov 18 – 21, 2026

Screened tropical pool retreat with cozy lighting and resort-style vibes

Twilight backyard retreat with private putting green and screened patio

Coastal-inspired game room with pool table for fun indoor hangouts

Private backyard movie nights under the string lights

Cozy fire pit, outdoor movie nights, and a resort-style screened pool

Sunny Daze Getaway

4 bedrooms·2 baths

Seminole • Florida

$1,229.00 USD total for 3 nights

Dec 3 – 6, 2026

Our Private Beach with chairs and umbrellas all included!!

Just a day at our private beach

Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

2 bedrooms·1½ baths

Sarasota County • Florida

$1,200.01 USD total for 7 nights

Nov 29 – Dec 6, 2026

506 Siesta

2 bedrooms·2 baths

Sarasota • Florida

Private beach access is 350 steps from property gate

Incredible Pool

Gated access and covered parking

Enjoy meals inside or on the balcony

Beach, Bay, Food, Fun - 2BD/2BA

2 bedrooms·2 baths

Siesta Key • Florida

4.67(9 reviews)

$1,488.48 USD total for 5 nights

Nov 27 – Dec 2, 2026

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

1 bedroom·1 bath

Sarasota • Florida

5(71 reviews)

$427.00 USD total for 3 nights

Nov 28 – Dec 1, 2026

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

2 bedrooms·1 bath

Sarasota • Florida

$3,900.00 USD total for 30 nights

Nov 18 – Dec 18, 2026

Drone view of Crescent Property.

Crescent Siesta Key Unit 406.

2 bedrooms·2 baths

Siesta Key • Florida

5(76 reviews)

$5,422.84 USD $5,043.79 USD total for 7 nights

Dec 20 – 27, 2026

Best Deals on Siesta Key image 1

Best Deals on Siesta Key image 2

Best Deals on Siesta Key image 3

Best Deals on Siesta Key image 4

Best Deals on Siesta Key image 5

Best Deals on Siesta Key

1 bedroom·1 bath

Sarasota • Florida

4.72(155 reviews)

$532.00 USD total for 3 nights

Nov 22 – 25, 2026

Open-concept living with stylish dining area and stunning ocean-view balcony

Spacious Beachfront Condo with stunning Gulf views

Spacious Beachfront Condo with stunning Gulf views

Spacious Beachfront Condo with stunning Gulf views

Bright beachfront bedroom with private balcony and ocean views

Spacious Beachfront Condo with stunning Gulf views

3 bedrooms·2 baths

Indian Rocks Beach • Florida

4.64(11 reviews)

$1,178.52 USD total for 3 nights

Dec 10 – 13, 2026

Beachside Paradise | Steps to Sand & Sunsets image 1

Beachside Paradise | Steps to Sand & Sunsets image 2

Beachside Paradise | Steps to Sand & Sunsets image 3

Beachside Paradise | Steps to Sand & Sunsets image 4

Beachside Paradise | Steps to Sand & Sunsets image 5

Hart's Paradise @ Barefoot Beach

1 bedroom·1 bath

Indian Shores • Florida

4.77(82 reviews)

$634.00 USD total for 3 nights

Nov 30 – Dec 3, 2026

Master bedroom
King Size Bed
Sliding doors to balcony

Master Bedroom
King size bed

Master Bedroom
42" Roku TV

Master bedroom
Sliding doors to balcony

Master bedroom
Reading chair with view of beach

Sea Gate 206 Beautiful Beach Front Condo/3 BR - 2 BTH

3 bedrooms·2 baths

Indian Shores • Florida

5(180 reviews)

$1,339.05 USD total for 3 nights

Nov 30 – Dec 3, 2026

Bay Shores Yacht & Tennis Club

Bay Shores Yacht & Tennis Club

Bay Shores Yacht & Tennis Club

Bay Shores Yacht & Tennis Club

Bay Shores Yacht & Tennis Club

Bay Shores Yacht & Tennis Club

2 bedrooms·2 baths

Indian Shores • Florida

$1,817.04 USD total for 7 nights

Jan 4 – 11, 2027

Family Resort | Pool • Mini Golf • Near Beach image 1

Family Resort | Pool • Mini Golf • Near Beach image 2

Family Resort | Pool • Mini Golf • Near Beach image 3

Family Resort | Pool • Mini Golf • Near Beach image 4

Family Resort | Pool • Mini Golf • Near Beach image 5

Family Resort | Pool • Mini Golf • Near Beach

4 bedrooms·2 baths

Seminole • Florida

5(2 reviews)

$1,337.00 USD total for 3 nights

Nov 22 – 25, 2026

Holiday Villa II #103 Beachside Condo

Holiday Villa II #103 Beachside Condo

Holiday Villa II #103 Beachside Condo

Holiday Villa II #103 Beachside Condo

Holiday Villa II #103 Beachside Condo

Holiday Villa II #103 Beachside Condo

2 bedrooms·2 baths

Indian Shores • Florida

5(86 reviews)

$1,566.18 USD total for 4 nights

Dec 6 – 10, 2026

No Crossing the Street You are Staying ON THE BEACH

Miles of Powder White Sand

Jump in the Gulf When it's Time for Water Break

Play doubles or 3x3 or 6x6

Living Room w/Recliners

Beach Paradise w/Balcony+Pool

2 bedrooms·2 baths

Indian Rocks Beach • Florida

4.6(5 reviews)

$1,985.41 USD total for 4 nights

Dec 4 – 8, 2026