Location

Dates

Guests

Vacation rentals in Holiday, Florida, United States

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)

5520,00 $ USD total por 3 noites

24/10/2026 – 27/10/2026

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

3158,35 $ USD total por 3 noites

24/10/2026 – 27/10/2026

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)

905,00 $ USD total por 3 noites

24/10/2026 – 27/10/2026

Tampa Heights Prohibition Era Bungalow image 1

Tampa Heights Prohibition Era Bungalow image 2

Tampa Heights Prohibition Era Bungalow image 3

Tampa Heights Prohibition Era Bungalow image 4

Tampa Heights Prohibition Era Bungalow image 5

Tampa Heights Prohibition Era Bungalow

3 bedrooms·2 baths

Tampa • Florida

5(19 reviews)

862,00 $ USD total por 3 noites

29/10/2026 – 01/11/2026

The Riverside Retreat (designer home w/ fire pit)

Fire Pit Seating

The Riverside Retreat (designer home w/ fire pit)

4 bedrooms·2 baths

Tampa • Florida

4.96(49 reviews)

894,00 $ USD total por 3 noites

02/11/2026 – 05/11/2026

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 por 3 noites

15/11/2026 – 18/11/2026

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)

1333,40 $ USD total por 5 noites

16/11/2026 – 21/11/2026

Newly renovated and decorated with modern leather sectional, contemporary entertainment center console with 65" TV.

Modern Family Condo near Busch Gardens, USF, Pool

Modern Family Condo near Busch Gardens, USF, Pool

King Size Zen Platform bed with Soft Memory Foam Mattress.

Modern Family Condo near Busch Gardens, USF, Pool

Modern Family Condo near Busch Gardens, USF, Pool

2 bedrooms·2 baths

Temple Terrace • Florida

5(5 reviews)

804,23 $ USD total por 4 noites

24/10/2026 – 28/10/2026

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 por 3 noites

25/10/2026 – 28/10/2026

Welcome to Emperor Rentals!

Prepare and make great meals in our wonderful spacious and fully equipped kitchen. If you love cooking, this property is great for you! Book it now!

Our large living area with comfortable L-Shaped modern couch will ensure a great and relaxing time for all of our guests. If you have any questions about this property, please send us an inquiry today!

Relax after a long day of activities with family and friends. Have an amazing sleep in this beautiful room that has a queen-size bed, TV, drawers, and closet.

Aerial side view of our amazing property! Worry not about kids playing in the fully fenced backyard during your stay! Inquire about this property now!

Paradise Cove House

4 bedrooms·1 bath

Pinellas Park • Florida

5(59 reviews)

807,47 $ USD 715,80 $ USD total por 3 noites

24/10/2026 – 27/10/2026

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

4299,65 $ USD total por 3 noites

24/10/2026 – 27/10/2026

Tampa Chalet Cabin near Busch Gardens Moffitt USF image 1

Tampa Chalet Cabin near Busch Gardens Moffitt USF image 2

Tampa Chalet Cabin near Busch Gardens Moffitt USF image 3

Tampa Chalet Cabin near Busch Gardens Moffitt USF image 4

Tampa Chalet Cabin near Busch Gardens Moffitt USF image 5

Tampa Chalet Cabin near Busch Gardens Moffitt USF

1 bedroom·1 bath

Tampa • Florida

5(7 reviews)

715,30 $ USD total por 3 noites

24/10/2026 – 27/10/2026

Welcome to Emperor Rentals!

Make the most of your stay with our amazing heated pool while grilling steaks and burgers on the side. Great spacious area for friends and family to create wonderful memories together. Inquire now!

Never miss a story or activity while doing your chores in this stunning open area where you can access our kitchen, living, and dining area! Don't hesitate to send us a message!

Elegant bedroom with king size bed, smart TV and own bathroom. Enjoy the comfort while staying at your home far from home. Do you love what you see? Don't think twice and send us an inquiry as soon as possible!

Great spacious area for friends and family to create wonderful memories together. Make the most of your stay with our amazing heated pool while grilling steaks and burgers on the side. Book this property now!

Tampa Tranquility

4 bedrooms·2 baths

Tampa • Florida

5(47 reviews)

967,70 $ USD total por 3 noites

25/10/2026 – 28/10/2026

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)

1430,00 $ USD total por 3 noites

09/10/2027 – 12/10/2027

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)

575,00 $ USD total por 3 noites

24/10/2026 – 27/10/2026

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

1428,16 $ USD 1280,64 $ USD total por 3 noites

24/10/2026 – 27/10/2026

Chic 2BR w/ Pool + Pet-Friendly | Unit #14

Chic 2BR w/ Pool + Pet-Friendly | Unit #14

Chic 2BR w/ Pool + Pet-Friendly | Unit #14

Chic 2BR w/ Pool + Pet-Friendly | Unit #14

Chic 2BR w/ Pool + Pet-Friendly | Unit #14

Chic 2BR w/ Pool + Pet-Friendly | Unit #14

2 bedrooms·2 baths

Tampa • Florida

18 216,16 $ USD 14 623,44 $ USD total por 28 noites

07/02/2027 – 07/03/2027

Stylish 2BR w/ Balcony, Pool & Pet-Friendly #15

Stylish 2BR w/ Balcony, Pool & Pet-Friendly #15

Stylish 2BR w/ Balcony, Pool & Pet-Friendly #15

Stylish 2BR w/ Balcony, Pool & Pet-Friendly #15

Stylish 2BR w/ Balcony, Pool & Pet-Friendly #15

Stylish 2BR w/ Balcony, Pool & Pet-Friendly #15

2 bedrooms·2 baths

Tampa • Florida

886,48 $ USD 823,09 $ USD total por 3 noites

27/10/2026 – 30/10/2026

Stylish 2BR w/ Pool + Pet-Friendly | Unit #13

Stylish 2BR w/ Pool + Pet-Friendly | Unit #13

Stylish 2BR w/ Pool + Pet-Friendly | Unit #13

Stylish 2BR w/ Pool + Pet-Friendly | Unit #13

Stylish 2BR w/ Pool + Pet-Friendly | Unit #13

Stylish 2BR w/ Pool + Pet-Friendly | Unit #13

2 bedrooms·2 baths

Tampa • Florida

878,57 $ USD 815,97 $ USD total por 3 noites

27/10/2026 – 30/10/2026

Modern 2BR w/ Pool + Pet-Friendly | Unit #16

Modern 2BR w/ Pool + Pet-Friendly | Unit #16

Modern 2BR w/ Pool + Pet-Friendly | Unit #16

Modern 2BR w/ Pool + Pet-Friendly | Unit #16

Modern 2BR w/ Pool + Pet-Friendly | Unit #16

Modern 2BR w/ Pool + Pet-Friendly | Unit #16

2 bedrooms·2 baths

Tampa • Florida

5(1 review)

806,25 $ USD 750,88 $ USD total por 3 noites

25/10/2026 – 28/10/2026

Modern 2BR w/ Pool | Pet-Friendly | Unit #17

Modern 2BR w/ Pool | Pet-Friendly | Unit #17

Modern 2BR w/ Pool | Pet-Friendly | Unit #17

Modern 2BR w/ Pool | Pet-Friendly | Unit #17

Modern 2BR w/ Pool | Pet-Friendly | Unit #17

Modern 2BR w/ Pool | Pet-Friendly | Unit #17

2 bedrooms·2 baths

Tampa • Florida

4(1 review)

1088,75 $ USD 1005,13 $ USD total por 3 noites

31/10/2026 – 03/11/2026

Modern 2BR w/ Pool + Pet-Friendly | Unit #18

Modern 2BR w/ Pool + Pet-Friendly | Unit #18

Modern 2BR w/ Pool + Pet-Friendly | Unit #18

Modern 2BR w/ Pool + Pet-Friendly | Unit #18

Modern 2BR w/ Pool + Pet-Friendly | Unit #18

Modern 2BR w/ Pool + Pet-Friendly | Unit #18

2 bedrooms·2 baths

Tampa • Florida

802,86 $ USD 747,83 $ USD total por 3 noites

27/10/2026 – 30/10/2026

Modern 2BR w/ Pool + Pet-Friendly | Unit #19

Modern 2BR w/ Pool + Pet-Friendly | Unit #19

Modern 2BR w/ Pool + Pet-Friendly | Unit #19

Modern 2BR w/ Pool + Pet-Friendly | Unit #19

Modern 2BR w/ Pool + Pet-Friendly | Unit #19

Modern 2BR w/ Pool + Pet-Friendly | Unit #19

2 bedrooms·2 baths

Tampa • Florida

861,62 $ USD 800,71 $ USD total por 3 noites

27/10/2026 – 30/10/2026

Modern 2BR w/ Pool + Pet-Friendly | Unit #23

Modern 2BR w/ Pool + Pet-Friendly | Unit #23

Modern 2BR w/ Pool + Pet-Friendly | Unit #23

Modern 2BR w/ Pool + Pet-Friendly | Unit #23

Modern 2BR w/ Pool + Pet-Friendly | Unit #23

Modern 2BR w/ Pool + Pet-Friendly | Unit #23

2 bedrooms·2 baths

Tampa • Florida

768,96 $ USD 717,32 $ USD total por 3 noites

26/10/2026 – 29/10/2026