Location

Dates

Guests

Vacation rentals in Indian Shores

Stylish retreat with heated pool, hot tub, game room, and bright modern interiors

Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach

Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach

Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach

Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach

Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach

3 bedrooms·2 baths

Largo • Florida

5(17 reviews)

$1,003.75 USD total for 3 nights

Oct 25 – 28, 2026

Outdoor seating with Heated Pool

Pool Home-Close to Beach/St Pete

3 bedrooms·2 baths

Largo • Florida

$213 – $391/ night(excl. fees & taxes)

Kitchen and Dining Area

The Walters

3 bedrooms·2 baths

St. Petersburg • Florida

5(21 reviews)

$774.05 USD $737.61 USD total for 3 nights

Oct 19 – 22, 2026

Funshine Flamingo's Nest

Funshine Flamingo's Nest

Funshine Flamingo's Nest

Funshine Flamingo's Nest

Funshine Flamingo's Nest

Funshine Flamingo's Nest

1 bedroom·1 bath

Largo • Florida

$765.90 USD total for 4 nights

Jan 31 – Feb 4, 2027

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

1 bedroom·1 bath

Madeira Beach • Florida

$567.00 USD total for 3 nights

Oct 19 – 22, 2026

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

1 bedroom·1 bath

Madeira Beach • Florida

$567.00 USD total for 3 nights

Oct 19 – 22, 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)

$550.00 USD total for 3 nights

Oct 19 – 22, 2026

Peaceful Pond Paradise

Peaceful Pond Paradise

Peaceful Pond Paradise

Peaceful Pond Paradise

Front seating area

Peaceful Pond Paradise

3 bedrooms·2 baths

Largo • Florida

5(10 reviews)

$582.00 USD total for 3 nights

Oct 19 – 22, 2026

Gulf Breeze Getaway - Sand Key image 1

Gulf Breeze Getaway - Sand Key image 2

Gulf Breeze Getaway - Sand Key image 3

Gulf Breeze Getaway - Sand Key image 4

Gulf Breeze Getaway - Sand Key image 5

Gulf Breeze Getaway - Sand Key

2 bedrooms·2 baths

Clearwater • Florida

$5,650.00 USD total for 30 nights

Oct 19 – Nov 18, 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

$4,477.06 USD total for 3 nights

Oct 19 – 22, 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

$1,539.06 USD total for 3 nights

Oct 19 – 22, 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

$1,380.16 USD total for 3 nights

Oct 19 – 22, 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

$1,253.04 USD total for 3 nights

Oct 19 – 22, 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

$1,298.44 USD total for 3 nights

Oct 19 – 22, 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

$1,298.44 USD total for 3 nights

Oct 19 – 22, 2026

The Parkside Retreat at 78th Street

3 bedrooms·2 baths

Pinellas Park • Florida

$791.29 USD total for 3 nights

Oct 20 – 23, 2026

Welcome to Emperor Rentals!

The PlayStation delivers endless entertainment options for players of all interests.

Have an amazing barbecue party while swimming with family and friends!

Comfortable bed to ensure you get the rest you deserve your entire stay

Enjoy this lovely trip with your family and friends while swimming in this pool

Serenity Stay Villa

4 bedrooms·2 baths

Largo • Florida

5(26 reviews)

$945.09 USD $837.55 USD total for 3 nights

Oct 19 – 22, 2026

"If your in Clearwater don't think twice this place it is great!! Jack and Shelly really out did them self. My new home every time we come. Don't miss out!"
- Cortney

Waterfront Condo | Steps to Clearwater Beach 2King

" My favorite place to be was the large patio, soaking in the sights and sounds of the bay. I definitely would love to go back!"
- Kristine

"The place was gorgeous and well worth the price."
- Rob

"My family very much enjoyed our stay in Clearwater beach and waking up to the gorgeous views of Clearwater Bay. The unit was large and very clean with a lot of helpful items (many kitchen utensils and products, beach towels and chairs, games, etc). We were sad to leave!"
- Sierra

Waterfront Condo | Steps to Clearwater Beach 2King

3 bedrooms·2 baths

Clearwater • Florida

$1,477.00 USD total for 3 nights

Oct 19 – 22, 2026

Front door to unit

Entrance Stairs

Closet in Kitchen area

The Blue House in Clearwater

2 bedrooms·1 bath

Clearwater • Florida

$3,559.50 USD total for 30 nights

Oct 19 – Nov 18, 2026

Mermaid Manor. Only 2 block to the BEACH!

Mermaid Manor - Waterfront | Dolphins & Sunsets

Mermaid Manor - Waterfront | Dolphins & Sunsets

Mermaid Manor - Waterfront | Dolphins & Sunsets

Mermaid Manor - Waterfront | Dolphins & Sunsets

Mermaid Manor - Waterfront | Dolphins & Sunsets

2 bedrooms·2 baths

Treasure Island • Florida

$699.78 USD total for 3 nights

Oct 19 – 22, 2026

Funshine Pointe Capri - Newly Renovated - Intercoastal Views

Funshine Pointe Capri - Newly Renovated - Intercoastal Views

Funshine Pointe Capri - Newly Renovated - Intercoastal Views

Funshine Pointe Capri - Newly Renovated - Intercoastal Views

Funshine Pointe Capri - Newly Renovated - Intercoastal Views

Funshine Pointe Capri - Newly Renovated - Intercoastal Views

1 bedroom·1 bath

Treasure Island • Florida

5(178 reviews)

$453.66 USD total for 3 nights

Oct 19 – 22, 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)

$7,524.00 USD total for 30 nights

Oct 23 – Nov 22, 2026

Your private pool, heated year-round to 80°F and ready for fall swims. Sun loungers and an umbrella line the deck, and the fully fenced backyard keeps the fun contained.

Red Adirondack chairs circle the fire pit under café lights. Fall evenings in Clearwater were made for slow talks and s'mores.

The whole backyard in one frame: heated pool, lounge chairs and cornhole on the lawn. Kids play, grown-ups relax, all inside a fenced yard.

Open-concept living made for your whole crew: a colorful mural, big sectional and dining table in one bright space, so nobody is stuck in another room while dinner comes together.

King primary suite with green and gold accents, a smart TV and ceiling fan. Your own retreat at the end of the day.

Heated pool, fire pit, games · dog friendly

3 bedrooms·2 baths

Clearwater • Florida

$1,058.50 USD total for 3 nights

Oct 19 – 22, 2026

A little piece of Beach House Heaven!

Waterfront Beach House Steps Away from #1 Beach!

Master Bedroom Balcony!

2nd floor (main living space) with gourmet kitchen and waterfront balcony attached!

Waterfront Beach House Steps Away from #1 Beach!

3 bedrooms·2 baths

Pinellas County • Florida

5(60 reviews)

$2,094.16 USD total for 3 nights

Oct 19 – 22, 2026