Location

Dates

Guests

Vacation rentals in Anna Maria, Florida, United States

The tiny home sits on a private 1.5 acre inland peninsula!

[Patio] Shared outdoor living space with fire pit

[Living area] This luxury 270sqft craftsman style tiny home is in the ideal location for your beach getaway.

Outdoor dining options available in the screened in lounge.

[Kitchen] Fully equipped kitchen featuring stainless steel appliances & gas cooktop. Coffee maker for all the coffee lovers out there!

·@Tiffanythetinyhome| island | netflix|bike|hammock

1 bedroom·1 bath

Sarasota • Florida

$452.00 USD total for 3 nights

Nov 18 – 21, 2026

[Living area] Smart TV with Netflix & Hulu

Waterfront tiny home sits on a private 1.5 acre inland peninsula! The perfect location for bird watching & kayaking around the lake.

[Living area] Doorway to the left leads into the main bedroom.

[Kitchen] Fully stocked & equipped kitchen with large farm sink and convection cooktop.

[Living area] French doors open up into the spacious backyard. Sofa converts into a bed for additional sleeping space.

@Shellmateisland |tiny home| island| bikes| kayaks

1 bedroom·1 bath

Sarasota • Florida

$574.00 USD total for 3 nights

Nov 18 – 21, 2026

Lakeside Retreat-4plex Sleeps 20

Lakeside Retreat-4plex Sleeps 20

Lakeside Retreat-4plex Sleeps 20

Lakeside Retreat-4plex Sleeps 20

Lakeside Retreat-4plex Sleeps 20

Lakeside Retreat-4plex Sleeps 20

9 bedrooms·5 baths

Largo • Florida

$3,135.75 USD total for 3 nights

Nov 18 – 21, 2026

Welcome to the Lakeside Retreat -This tranquil estate awaits!

Nestled right on Lake Seminole, the backyard gazebo and pool area provide stunning views!

Our unique 4-plex floor plan gives your large group the ability to gather…

…while still having moments of privacy in their own suites.

Each suite is inspired by one of the 4 elements: Earth, Air, Fire, & Water

Lakeside Retreat-4plex Sleeps 20

9 bedrooms·5 baths

Largo • Florida

5(19 reviews)

$5,520.00 USD total for 3 nights

Nov 18 – 21, 2026

Family & pet friendly 4-bedroom home • heated pool image 1

Front of the house

Family & pet friendly 4-bedroom home • heated pool image 4

Family & pet friendly 4-bedroom home • heated pool image 5

Family & pet friendly 4-bedroom home • heated pool

4 bedrooms·2 baths

Largo • Florida

4.72(133 reviews)

$820.00 USD total for 3 nights

Nov 18 – 21, 2026

Comfy Living Room with 55" TV

Center Open view

Kitchen w/beverage fridge

Indian Rocks Beach only 2.5 miles - 4 bed & 2 bath

4 bedrooms·2 baths

Seminole • Florida

$1,401.75 USD total for 3 nights

Nov 18 – 21, 2026

Dining room with views of the pool.

Enjoy golden hour from the private outdoor deck and pool.

Open layout kitchen and living room.

Cozy living room.

Enjoy a game of air hockey or ping pong.

Paradise Passage

4 bedrooms·3 baths

Seminole • Florida

$1,555.98 USD $1,497.13 USD total for 3 nights

Nov 18 – 21, 2026

Outdoor seating with Heated Pool

Pool Home-Close to Beach/St Pete

3 bedrooms·2 baths

Largo • Florida

$331/ night(excl. fees & taxes)

Your beach getaway in the Largo/Seminole paradise!

Lovely fire after a day at the beach and a tasty BBQ!

Large private backyard!

Living room w/Roku TV, Games, DVD player w/DVDs, Books & Local Info! Sofa Bed is a Queen size MEMORY FOAM that is so comfortable!

No Wake Queen Bedroom with Roku TV, a bookshelf, 2 nightstands, a dresser and two closet areas.

Hannah House Vacation Rentals

5 bedrooms·2 baths

Largo • Florida

$1,081.47 USD $1,042.89 USD total for 3 nights

Nov 18 – 21, 2026

private pool in backyard

new refrigerator

view from front door

bright and spacious living room

private lap pool and patio furniture

Captain's Cove with pool in Sunny Largo, FL

2 bedrooms·1 bath

Largo • Florida

$949.81 USD total for 3 nights

Dec 21 – 24, 2026

Lake Sarasota image 1

Lake Sarasota image 2

Lake Sarasota image 3

Lake Sarasota image 4

Lake Sarasota image 5

Lake Sarasota

4 bedrooms·2 baths

Sarasota • Florida

4.77(53 reviews)

$991.01 USD total for 3 nights

Dec 6 – 9, 2026

air conditioned sun room

beach living room

Paradise Place, Pets/Ms. Pac Man

Paradise Place, Pets/Ms. Pac Man

2 bedrooms·2 baths

Largo • Florida

$1,716.26 USD total for 4 nights

Apr 1 – 5, 2027

air conditioned sun room

beach living room

Paradise Place, Pets/Ms. Pac Man

Paradise Place, Pets/Ms. Pac Man

2 bedrooms·2 baths

Largo • Florida

$1,716.26 USD total for 4 nights

Apr 1 – 5, 2027

The private year-round pool at Twin Oaks, surrounded by tropical landscaping within the screened outdoor retreat—approximately 5–10 minutes from Indian Rocks Beach, depending on traffic and beach parking.

Screened pool, cozy fire table, and bright coastal-style interiors

Private tree-lined home with screened pool in a peaceful neighborhood

Bright coastal living space with fireplace and large dining table

A bright, airy second living space with white slipcovered sofas, a distressed wood coffee table, starfish accents, and large plantation shuttered windows overlooking lush Florida greenery.

Twin Oaks Luxury Heated Pool and Caribbean Tiki Bar Near Indian Rocks Beach

4 bedrooms·3 baths

Largo • Florida

5(51 reviews)

$1,440.93 USD total for 3 nights

Dec 7 – 10, 2026

9BR Heated Pool • Hot Tub • Golf Simulator

9BR Heated Pool • Hot Tub • Golf Simulator

9BR Heated Pool • Hot Tub • Golf Simulator

9BR Heated Pool • Hot Tub • Golf Simulator

9BR Heated Pool • Hot Tub • Golf Simulator

9BR Heated Pool • Hot Tub • Golf Simulator

9 bedrooms·4 baths

Largo • Florida

$4,819.45 USD total for 3 nights

Nov 18 – 21, 2026

Largo Waterview 6BR Heated Pool/Hot Tub GameRoom

5 bedrooms·4 baths

Largo • Florida

5(9 reviews)

$7,200.00 USD $6,648.00 USD total for 3 nights

Nov 18 – 21, 2026

4br apollo beach home free heater pool & waterfall image 1

4br apollo beach home free heater pool & waterfall image 2

4br apollo beach home free heater pool & waterfall image 3

4br apollo beach home free heater pool & waterfall image 4

4br apollo beach home free heater pool & waterfall image 5

4br apollo beach home free heater pool & waterfall

4 bedrooms·3 baths

Apollo Beach • Florida

4.94(53 reviews)

$1,405.00 USD total for 3 nights

Nov 18 – 21, 2026

Beautiful Sarasota villa in a quiet tropical setting with a screened lanai for comfortable outdoor living. Surrounded by palm trees and lush landscaping, this peaceful retreat offers privacy and relaxation just minutes from beaches and attractions.

Sarasota Villa with Pool Access Tennis Near Beach image 2

Sarasota Villa with Pool Access Tennis Near Beach image 3

Sarasota Villa with Pool Access Tennis Near Beach image 4

Sarasota Villa with Pool Access Tennis Near Beach image 5

Sarasota Villa with Pool Access Tennis Near Beach

2 bedrooms·2 baths

Sarasota • Florida

5(5 reviews)

$1,543.58 USD total for 7 nights

Dec 1 – 8, 2026

Private backyard retreat with hot tub, fire pit & outdoor dining under café lights

Relax under the courtyard pergola beside the fire table in your private outdoor lounge.

Relax in the hot tub beneath the pergola with bar seating and ambient string lights.

Spacious great room with plenty of comfortable seating for the whole group to relax together.

Primary king suite with a private office and en suite bath.

The Salted Dream House

5 bedrooms·2½ baths

Largo • Florida

$1,708.06 USD total for 3 nights

Nov 18 – 21, 2026

Apollo Beach 4BR Retreat - The Fountain House, Private Pool

Apollo Beach 4BR Retreat - The Fountain House, Private Pool

Apollo Beach 4BR Retreat - The Fountain House, Private Pool

Apollo Beach 4BR Retreat - The Fountain House, Private Pool

Apollo Beach 4BR Retreat - The Fountain House, Private Pool

Apollo Beach 4BR Retreat - The Fountain House, Private Pool

4 bedrooms·3 baths

Apollo Beach • Florida

5(79 reviews)

$2,305.00 USD total for 6 nights

Dec 14 – 20, 2026

Gulf front pool

Front of the building

Hallway into condo

Sand Isle I

2 bedrooms·2 baths

Indian Rocks Beach • Florida

4.77(100 reviews)

$847.50 USD total for 3 nights

Dec 6 – 9, 2026

Spacious living room.

Fully equipped kitchen and plenty of seating

Open concept living room

Beach AND Pool!2/2 large condo

2 bedrooms·2 baths

Indian Rocks Beach • Florida

5(152 reviews)

$1,378.60 USD total for 5 nights

Nov 18 – 23, 2026

Beautiful Waterfront Condo short walk to the beach image 1

Beautiful Waterfront Condo short walk to the beach image 2

Beautiful Waterfront Condo short walk to the beach image 3

Beautiful Waterfront Condo short walk to the beach image 4

Beautiful Waterfront Condo short walk to the beach image 5

Romantic Waterfront Getaway short walk to beach

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$3,586.60 USD $2,960.08 USD total for 29 nights

Nov 18 – Dec 17, 2026

Tropical Beach Escape image 1

Tropical Beach Escape image 2

Sunset pool retreat with in-water loungers and screened patio

2 queen foam mattresses
Full length closet mirrors
USB port
Luggage racks
Ceiling fan
Large dresser for more space for your items
Smart TV with remote
iron, steamer and ironing board in closet
box fans in closet

Make up towel and face wipes
shampoo, conditioner, body wash
wash clothes, bath towels
Qtips
Cotton balls

Tropical Escape Near the Beach with Heated Pool

3 bedrooms·2 baths

Largo • Florida

4.94(63 reviews)

$1,915.00 USD total for 3 nights

Jan 1 – 4, 2027