Location

Dates

Guests

Vacation rentals in Largo

Mid day snacks by the pool are always nice too.

The spacious master bath offers dual vanities to allow quick prep for the beach.

There is always a late afternoon, early evening kayak option.

Or, sea side putting practice before dinner?

The smart TV in the kitchen allows the cook to enjoy the game or movie also.

Aloha Paradise

3 bedrooms·3 baths

Indian Rocks Beach • Florida

5(20 reviews)

$2,099.54 USD total for 3 nights

Oct 26 – 29, 2026

Urban Escape: Artificial Beach W/Volleyball Pit

Urban Escape: Artificial Beach W/Volleyball Pit

Urban Escape: Artificial Beach W/Volleyball Pit

Urban Escape: Artificial Beach W/Volleyball Pit

Urban Escape: Artificial Beach W/Volleyball Pit

Urban Escape: Artificial Beach W/Volleyball Pit

4 bedrooms·3 baths

Clearwater • Florida

4.78(9 reviews)

$400 – $450/ night(excl. fees & taxes)

Living room with natural lighting.

Fenced backyard with patio and seating.

Inquire About Discounted Rental Rate

Maxwell Sands

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$1,090.88 USD $982.50 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

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)

$1,430.00 USD total for 3 nights

Oct 9 – 12, 2027

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

Driftwood Sands #307

Driftwood Sands #307

Driftwood Sands #307

Driftwood Sands #307

Driftwood Sands #307

Driftwood Sands #307

3 bedrooms·2 baths

Indian Rocks Beach • Florida

5(4 reviews)

$6,182.23 USD total for 28 nights

Nov 30 – Dec 28, 2026

Sweet Craftsman home, free bikes, near beach & DT image 1

Sweet Craftsman home, free bikes, near beach & DT image 2

Sweet Craftsman home, free bikes, near beach & DT image 3

Sweet Craftsman home, free bikes, near beach & DT image 4

Sweet Craftsman home, free bikes, near beach & DT image 5

Adorable Private Craftsman

2 bedrooms·1 bath

Clearwater • Florida

4.86(267 reviews)

$532.00 USD $511.15 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

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

$2,584.20 USD total for 4 nights

Oct 19 – 23, 2026

Beautiful View Overlooking Canal, Dock, and Lift

Aerial View of Back of Property

Welcome to Villa Azure

V Azule- Evening- Canal, Lift

V Azule- Outside Dining-Patio

Villa Azule | Luxury Waterfront Retreat • Walk to Indian Rocks Beach

4 bedrooms·5 baths

Indian Rocks Beach • Florida

4.88(146 reviews)

$2,065.13 USD total for 3 nights

Oct 26 – 29, 2026

What could be more Florida than daquiries poolside?

Swimming in a heated pool at night?

Azul Paradise

5 bedrooms·4 baths

Indian Rocks Beach • Florida

5(41 reviews)

$2,208.02 USD $2,127.51 USD total for 3 nights

Oct 19 – 22, 2026

Oceanway Condos #205

Oceanway Condos #205

Oceanway Condos #205

Oceanway Condos #205

Oceanway Condos #205

Oceanway Condos #205

2 bedrooms·2 baths

Indian Rocks Beach • Florida

$1,812.19 USD total for 7 nights

Oct 19 – 26, 2026

Sea Isles Condo E

Sea Isles Condo E

Sea Isles Condo E

Sea Isles Condo E

Sea Isles Condo E

Sea Isles Condo E

2 bedrooms·2 baths

Indian Rocks Beach • Florida

$2,526.83 USD total for 7 nights

Oct 19 – 26, 2026

Sea Isles Condo L

Sea Isles Condo L

Sea Isles Condo L

Sea Isles Condo L

Sea Isles Condo L

Sea Isles Condo L

2 bedrooms·2 baths

Indian Rocks Beach • Florida

$2,266.11 USD total for 7 nights

Oct 19 – 26, 2026

Two blocks to bliss/beach

Two blocks to bliss/beach

Two blocks to bliss/beach

Two blocks to bliss/beach

Two blocks to bliss/beach

Two blocks to bliss/beach

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$972.34 USD total for 3 nights

Oct 19 – 22, 2026

Sugar Sands Retreat #2

Sugar Sands Retreat #2

Sugar Sands Retreat #2

Sugar Sands Retreat #2

Sugar Sands Retreat #2

Sugar Sands Retreat #2

1 bedroom·1 bath

Indian Rocks Beach • Florida

$506.07 USD total for 3 nights

Oct 19 – 22, 2026

Sugar Sands Retreat #3

Sugar Sands Retreat #3

Spacious yard for relaxing

Sugar Sands Retreat #3

1 bedroom·1 bath

Indian Rocks Beach • Florida

$557.17 USD total for 3 nights

Oct 30 – Nov 2, 2026

Vaulted ceilings with modern coastal feel

Sofa bed for extra guests

Sugar Sands Retreat #1

King bed with ensuite

Try standup paddle boarding

Sugar Sands Retreat #1

1 bedroom·1 bath

Indian Rocks Beach • Florida

$646.64 USD total for 3 nights

Oct 30 – Nov 2, 2026

Sunset Paradise #3

Sunset Paradise #3

Sunset Paradise #3

Sunset Paradise #3

Sunset Paradise #3

Sunset Paradise #3

3 bedrooms·2 baths

Indian Rocks Beach • Florida

Sunset Paradise #6

Sunset Paradise #6

Sunset Paradise #6

Sunset Paradise #6

Sunset Paradise #6

Sunset Paradise #6

2 bedrooms·2½ baths

Indian Rocks Beach • Florida

$1,080.28 USD total for 4 nights

Oct 19 – 23, 2026

Sunset Paradise #5

Sunset Paradise #5

Sunset Paradise #5

Sunset Paradise #5

Sunset Paradise #5

Sunset Paradise #5

2 bedrooms·2 baths

Indian Rocks Beach • Florida

$1,102.88 USD total for 4 nights

Oct 19 – 23, 2026

Bring your bike or enjoy the Complimentary bikes available. Actual model may varies. Pinellas trail is about 0.3 miles away, perfect for biking and walking.

Adorable Bungalow near beach, DT. Pet & Bike. image 2

Adorable Bungalow near beach, DT. Pet & Bike. image 3

Fully equipped kitchen.

Adorable Bungalow near beach, DT. Pet & Bike. image 5

Adorable Private Bungalow

2 bedrooms·1 bath

Clearwater • Florida

4.81(264 reviews)

$99 – $179/ night(excl. fees & taxes)

Coastal-style living room with fireplace, TV, and bright open seating

Coastal-chic living room with fireplace, built-ins, and inviting seating

Bright coastal living space with fireplace and large dining table

Screened pool patio with tiki bar, grill, and tropical lounge seating

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

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

4 bedrooms·3 baths

Largo • Florida

5(51 reviews)

$944.16 USD total for 3 nights

Oct 25 – 28, 2026