Location

Dates

Guests

Vacation rentals in Holiday, Florida, United States

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

$2,496.57 USD total for 7 nights

Sep 7 – 14, 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

$2,203.26 USD total for 7 nights

Sep 7 – 14, 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

$864.45 USD total for 3 nights

Sep 8 – 11, 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

$1,057.68 USD total for 4 nights

Sep 8 – 12, 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)

$2,145.87 USD total for 3 nights

Sep 13 – 16, 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

$229/ night(excl. fees & taxes)

Outdoor seating with Heated Pool

Pool Home-Close to Beach/St Pete

3 bedrooms·2 baths

Largo • Florida

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

What you see when you pull up

8103 N Klondyke Street-11What you see when you walk up

Perfectly appointed living space

8103 N Klondyke Street-13Custom built ins w/ fireplace and games

Perfectly appointed living space

Designer 4 BR. Chef's Kitchen. Gazebo Outdoor Retreat.

4 bedrooms·2 baths

Tampa • Florida

$862.87 USD total for 3 nights

Sep 30 – Oct 3, 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

$92 – $365/ night(excl. fees & taxes)

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

$92 – $368/ night(excl. fees & taxes)

Sugar Sands Retreat #3

Sugar Sands Retreat #3

Spacious yard for relaxing

Sugar Sands Retreat #3

1 bedroom·1 bath

Indian Rocks Beach • Florida

$97 – $318/ night(excl. fees & taxes)

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

$111 – $367/ night(excl. fees & taxes)

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

$111 – $367/ night(excl. fees & taxes)

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

$81 – $503/ night(excl. fees & taxes)

Reef Club #307

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$2,729.35 USD total for 7 nights

Sep 7 – 14, 2026

Blue Heron Cottage #1

Blue Heron Cottage #1

Blue Heron Cottage #1

Blue Heron Cottage #1

Blue Heron Cottage #1

Blue Heron Cottage #1

1 bedroom·1 bath

Indian Rocks Beach • Florida

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

$1,257.88 USD total for 3 nights

Sep 7 – 10, 2026

Beautiful View Overlooking Canal, Dock, and Lift

Aerial View of Back of Property

Sunset at Villa Azule

Evenings on the back patio

03 VA-exterior-front-night

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

Sep 7 – 10, 2026

250 steps to the Beach! image 1

250 steps to the Beach! image 3

250 steps to the Beach! image 4

250 steps to the Beach! image 5

250 steps to the Beach! image 6

250 steps to the Beach!

2 bedrooms·1 bath

Indian Rocks Beach • Florida

4.82(159 reviews)

$1,525.00 USD total for 7 nights

Sep 7 – 14, 2026

Waterfront Heated Pool & Hot Tub

Grab the free paddle board and explore the waters around Indian Rocks Beach

Add a 2nd 6-seater golf cart after booking so everyone can ride

Bahia Paradise

4 bedrooms·4 baths

Indian Rocks Beach • Florida

5(1 review)

$473 – $2,051/ night(excl. fees & taxes)

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

Beautiful Waterfront Condo 8 min walk to the beach

3 bedrooms·2 baths

Indian Rocks Beach • Florida

$4,832.83 USD $3,957.06 USD total for 29 nights

Oct 7 – Nov 5, 2026

The open floor plan features an 8-foot island, connecting the gourmet kitchen, living, and dining areas. Surrounded by palm and oak trees, large windows offer views of nature w french doors leading to the outdoor deck and fully enclosed backyard

Bright dining area with seating for 8, surrounded by large windows and French doors overlooking the property’s tropical greenery. Perfect for family dinners, morning coffee, or gathering after a day in Tampa Bay.

Modern Luxury | Fenced | Pet Friendly

The living area with seating for eight, has views of the private garden set amongst oak trees, palm trees, birds of paradise making it the perfect place to relax and unwind or connect with friends and family. The sofa features a pull out queen bed.

Guest Room Featuring a Queen bed, smart TV & dedicated workspace

Modern Luxury | Fenced | Pet Friendly

3 bedrooms·2½ baths

Tampa • Florida

5(1 review)

$829.45 USD total for 3 nights

Sep 13 – 16, 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.

Evening fire pit seating for the whole group, plus BBQ grill and outdoor dining

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

Comfortable Seating for Family Movie Nights

The Salted Dream House

5 bedrooms·2½ baths

Largo • Florida

$1,681.50 USD total for 3 nights

Sep 7 – 10, 2026