Location

Dates

Guests

Vacation rentals in Anna Maria, Florida, United States

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

2 bedrooms·2 baths

Sarasota • Florida

$31,480.00 USD total for 120 nights

Nov 18, 2026 – Mar 18, 2027

A serene and private fenced in Courtyard/Backyard with an outdoor grill.

Patio with Grill

Architecture details about the house

Open floor with Living Room, two Dining areas and Kitchen

Award winning ARCHITECT designed home DOWNTOWN&BAY

3 bedrooms·2½ baths

St. Petersburg • Florida

5(72 reviews)

$4,450.00 USD total for 30 nights

Nov 18 – Dec 18, 2026

Large 2 story bungalow home with huge front porch

Need a great place close to everything for your friends for your bachelorette party?

Bedroom with a bed in white bedding, nightstands with lamps, and a window with blinds.

Look what our guests say about our space

Living room with a beige sofa, wooden coffee table, wall-mounted TV, and bookshelves.

Entire historic micro resort for your event

9 bedrooms·6 baths

St. Petersburg • Florida

4.83(18 reviews)

$5,665.86 USD total for 3 nights

Feb 4 – 7, 2027

Front porch with turquoise front door

Pick up a share bike in the park and bike to the waterfront

Covered front porch with outdoor seating

A stroll in the park

Backyard lawn with deck seating and umbrellas

Spacious 3Unit Retreat great for Groups & Families

7 bedrooms·5 baths

St. Petersburg • Florida

5(2 reviews)

$3,496.65 USD total for 3 nights

Feb 7 – 10, 2027

Front porch with rocking chairs and seating by the turquoise front door

Large banyan tree with sprawling roots and branches in a grassy park

Bedroom with a white bed, black metal frame, nightstands, lamps, and a window with blinds

Park pond with a fountain, surrounded by trees and grass

Dining room with a wooden table, white chairs, large windows, and a sideboard

Spacious Family Stay - Pet Friendly

3 bedrooms·2 baths

St. Petersburg • Florida

4.8(205 reviews)

$1,029.96 USD total for 3 nights

Nov 30 – Dec 3, 2026

Welcome to our bungalow, The Banyan House in the Historic Uptown neighborhood

Beautiful park steps away

Small workspace nook with a wooden desk, chair, and plant by the windows

A stroll in the park

Front porch seating with cushioned chairs and a round table set with coffee cups

2x King en-Suites walkable Downtown Pet Friendly

2 bedrooms·2 baths

St. Petersburg • Florida

4.82(170 reviews)

$876.28 USD total for 3 nights

Dec 1 – 4, 2026

Welcome to our historic downtown bungalow

Book a dolphin tour with us

Stacked washer and dryer in a laundry nook

Group of guests outdoors holding pink and white balloons

Bedroom with white bedding, bedside tables, and a window overlooking palm trees

Sprawling 5BR Bungalow Home Perfect for Groups

5 bedrooms·4 baths

St. Petersburg • Florida

4.86(80 reviews)

$2,611.47 USD total for 3 nights

Feb 7 – 10, 2027

A bed for your wary heads

Get out and smell the roses

May I have a table for 2?

Sure

See the ugly duckling turned into a swan

Did someone say " let there be light" ???

The Twisted Tulip-a curious stay

1 bedroom·1 bath

St. Petersburg • Florida

4.86(7 reviews)

$517.73 USD total for 3 nights

Nov 22 – 25, 2026

Meet the Banyan
Just steps from your door, this majestic banyan tree in the neighborhood park inspired the name of our cozy retreat. Rooted in history, just like your next memory.

Cozy meets creative in this sunny lounge! Enjoy fast Wi-Fi, Smart TV, and artistic touches throughout—ideal for relaxing with a good show or planning your next St. Pete adventure.

Outdoor patio at night with seating, string lights, and a table set with wine and snacks.

Your Neighborhood Oasis
Just around the corner, unwind by the peaceful pond and fountain—perfect for a morning walk or a sunset stroll under the palms.

Vibrant gallery wall meets comfy sofa—this cozy corner is perfect for lounging, reading, or sharing a glass of wine in a bold, art-inspired setting.

Cozy Couples Artsy Retreat with Local Art Walkable

2 bedrooms·1 bath

St. Petersburg • Florida

4.76(270 reviews)

$100 – $396/ night(excl. fees & taxes)

Open living room with colorful rug, green sofa, and kitchen in the background

Relax with a book or journal—your peaceful, artistic corner

Enjoy the tranquility of our park

Park path beside a pond with a bench, trees, and green lawn

Cozy Dali Inspired Loft for Couples & Small Groups

2 bedrooms·1 bath

St. Petersburg • Florida

4.8(249 reviews)

$89 – $353/ night(excl. fees & taxes)

[Living area] Smart TV with Netflix & sofa bed

[Dining area] Free bikes, kayaks & beach gear are included in this rental!

[Kitchen] Fully stocked & equipped kitchen with updated appliances. Coffee maker & complimentary coffee provided.

[Living area] Smart TV with Netflix & sofa bed

Here's one of my 5-star reviews...improving every day!

Walk score 82 | bikes | kayak | 214mbps | foam bed

1 bedroom·1 bath

St. Petersburg • Florida

$747.00 USD total for 3 nights

Nov 18 – 21, 2026

[Entrance] Self-check in with keypad

[Exterior] Unit is located towards the back of the property

[Living area] Smart TV with Netflix

[Bathroom] Full size standing shower with plenty of warm water & great shower pressure.

[Living area] Sofa folds out into a sofa bed for additional sleeping space

Outskirt Downtown | 400ft² | bikes | kayak|netflix

1 bedroom·1 bath

St. Petersburg • Florida

$919.00 USD total for 3 nights

Nov 18 – 21, 2026

Chasing the Sun- Downtown Burns Court image 1

Chasing the Sun- Downtown Burns Court image 2

Chasing the Sun- Downtown Burns Court image 3

Chasing the Sun- Downtown Burns Court image 4

Chasing the Sun- Downtown Burns Court image 5

Chasing the Sun- Downtown Burns Court

2 bedrooms·1 bath

Sarasota • Florida

4.95(62 reviews)

$1,158.00 USD total for 7 nights

Dec 15 – 22, 2026

Cozy coastal living with Smart TV & relaxing vibe

Lido Beach Pool & Pavilion, The 25-meter lap pool is open Friday through Sunday, from 10:00 am to 4:30 pm, weather permitting. Fees apply.

Primary queen suite with private ensuite and plenty of natural light

Sunny dining area for morning coffee or family dinners

Lido Key | Steps to Beach, Walk to St. Armands

2 bedrooms·2 baths

Sarasota • Florida

4.97(39 reviews)

$1,328.00 USD total for 3 nights

Nov 18 – 21, 2026

Main living room with ample seating, dining today and bright sunshine gracing the windows.

Move the additional seating over to the couch after sitting down for dinner.

Dinner for 4. Quick and easy access to the full size kitchen for home cooked meals while on vacay.

Queen bed, with additional ceiling fans if you like it really cold and of course your very own private full bathroom. Also, ample closet space to fully stretch out.

Lido Key Beach Escape | 2 Private Suites

2 bedrooms·2 baths

Sarasota • Florida

4.95(21 reviews)

$1,239.92 USD total for 3 nights

Nov 30 – Dec 3, 2026

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

7 bedrooms·7 baths

Madeira Beach • Florida

$6,254.55 USD total for 3 nights

Nov 18 – 21, 2026

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

2 bedrooms·2 baths

Madeira Beach • Florida

$1,939.72 USD total for 3 nights

Nov 18 – 21, 2026

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath

Madeira Beach • Florida

$1,750.17 USD total for 3 nights

Nov 18 – 21, 2026

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath

Madeira Beach • Florida

$1,641.21 USD total for 3 nights

Nov 18 – 21, 2026

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

1 bedroom·1 bath

Madeira Beach • Florida

$1,590.14 USD total for 3 nights

Nov 18 – 21, 2026

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

1 bedroom·1 bath

Madeira Beach • Florida

$1,641.21 USD total for 3 nights

Nov 18 – 21, 2026

SeaBreeze 101-Sunsets, sand, pool! Free parking

SeaBreeze 101-Sunsets, sand, pool! Free parking

SeaBreeze 101-Sunsets, sand, pool! Free parking

SeaBreeze 101-Sunsets, sand, pool! Free parking

SeaBreeze 101-Sunsets, sand, pool! Free parking

SeaBreeze 101-Sunsets, sand, pool! Free parking

2 bedrooms·2 baths

Madeira Beach • Florida

5(31 reviews)

$1,350.35 USD total for 3 nights

Nov 27 – 30, 2026

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

4 bedrooms·2 baths

St. Petersburg • Florida

4.95(43 reviews)

$7,770.00 USD total for 30 nights

Nov 18 – Dec 18, 2026

Heated pool & spa

Bathroom 1 bath/shower

Bathroom 2 walk in shower

Heated Pool & Spa 3bd/2bth, near Siesta Key Beach

3 bedrooms·2 baths

Sarasota • Florida

$120 – $360/ night(excl. fees & taxes)