Location

Dates

Guests

Vacation rentals in Anna Maria, Florida, United States

Heated Saltwater Pool

The pool and surrounding area features enough lighting to enjoy the Florida evenings in style!

Catch the game on the 75" TV from the HOT TUB!

Newly remodeled kitchen with new stainless steel appliances (refrigerator, induction cook top, built in microwave/oven and dishwasher).

Living Room featuring a large sectional sofa and a 55" smart TV. Sit and enjoy the abundance of natural light.

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

Commonwealth

4 bedrooms·3½ baths

Siesta Key • Florida

$1,496.25 USD total for 3 nights

Nov 30 – Dec 3, 2026

Front of the house with 2 parking in driveway

Tropical Oasis On the Gulf Coast

Tropical Oasis On the Gulf Coast

Tropical Oasis On the Gulf Coast

Tropical Oasis On the Gulf Coast

Tropical Oasis On the Gulf Coast

2 bedrooms·2 baths

Seminole • Florida

$620.00 USD total for 3 nights

Nov 18 – 21, 2026

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

The Coffee Pot Cottage

2 bedrooms·1 bath

St. Petersburg • Florida

5(30 reviews)

$728.28 USD $602.62 USD total for 3 nights

Nov 27 – 30, 2026

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(40 reviews)

$594.15 USD $491.32 USD total for 3 nights

Nov 23 – 26, 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

$720.15 USD total for 3 nights

Nov 18 – 21, 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!

Enjoy your favorite movie or watch your favorite team on this nice smart TV and relax!

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

Breathtaking views off the living area!

Bahia Beach Calm Ruskin Retreat

2 bedrooms·1½ baths

Ruskin • Florida

$612.00 USD total for 3 nights

Nov 18 – 21, 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)

$3,701.06 USD total for 3 nights

Nov 18 – 21, 2026

The Coastal Anchor Suite #410 at Little Harbor Inn

The Coastal Anchor Suite #410 at Little Harbor Inn

The Coastal Anchor Suite #410 at Little Harbor Inn

The Coastal Anchor Suite #410 at Little Harbor Inn

The Coastal Anchor Suite #410 at Little Harbor Inn

The Coastal Anchor Suite #410 at Little Harbor Inn

1 bedroom·1 bath

Ruskin • Florida

$15.00 USD total for 3 nights

Nov 18 – 21, 2026

The Coastal Anchor Suite #307 at Little Harbor Inn

The Coastal Anchor Suite #307 at Little Harbor Inn

The Coastal Anchor Suite #307 at Little Harbor Inn

The Coastal Anchor Suite #307 at Little Harbor Inn

The Coastal Anchor Suite #307 at Little Harbor Inn

The Coastal Anchor Suite #307 at Little Harbor Inn

1 bedroom·1 bath

Ruskin • Florida

$449.97 USD total for 3 nights

Nov 18 – 21, 2026

See beautiful sunsets from our pool. Lots of outdoor lighting.

French Doors in the master suite open up to the screened in pool area.

Queen bed with 2 large closets and a desk.

Sitting area in the master bedroom.

Beautiful pool home in Paradise! 4 miles Siesta Key & Lido, 3 miles to downtown

3 bedrooms·2 baths

Sarasota • Florida

$1,300.00 USD total for 3 nights

Nov 28 – Dec 1, 2026

The Parkside Retreat at 78th Street

3 bedrooms·2 baths

Pinellas Park • Florida

$791.29 USD total for 3 nights

Nov 18 – 21, 2026

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

Dec 1 – 4, 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

Nov 18 – 21, 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)

$8,072.88 USD total for 3 nights

Nov 22 – 25, 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)

$2,141.35 USD total for 7 nights

Nov 21 – 28, 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(4 reviews)

$5,391.20 USD total for 7 nights

Dec 7 – 14, 2026

Wall mounted flat screens in LR and each bedroom.

New kitchen just completed Jan, '20 - all wood cabinets, granite countertops.

Private kitchen

Private Pinellas County Beaches' getaway house

2 bedrooms·1 bath

Seminole • Florida

4.17(63 reviews)

$311.88 USD total for 3 nights

Apr 17 – 20, 2027

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

$3,329.77 USD total for 14 nights

Nov 18 – Dec 2, 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

$2,383.23 USD total for 14 nights

Dec 4 – 18, 2026

The main living room

Cute home w/ saltwater heated pool! 6 mi to beach! image 2

Cute home w/ saltwater heated pool! 6 mi to beach! image 3

Fire pit and hammocks

Cute home w/ saltwater heated pool! 6 mi to beach!

3 bedrooms·2 baths

Seminole • Florida

4.83(132 reviews)

$767.00 USD total for 3 nights

Nov 18 – 21, 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)

Step onto your private dock and enjoy peaceful canal views at White Heron Landing, your waterfront retreat in Ruskin, Florida.

Relax in the bright, coastal-inspired living room featuring a spacious sectional, large-screen TV, electric fireplace, and direct access to the screened lanai.

Enjoy outdoor meals and Florida breezes in the screened lanai, featuring a dining table, comfortable seating, and a grill.

Gather with family and friends in the bright, open-concept living, dining, and kitchen area, designed for relaxing and spending time together.

Explore White Heron Landing's beautiful waterfront setting, surrounded by scenic canals and the coastal community of Ruskin, Florida..

White Heron Landing

4 bedrooms·2 baths

Ruskin • Florida

$906.53 USD total for 3 nights

Nov 18 – 21, 2026