Compare villa rentals in Holiday, FL from 100+ providers!

50 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Holiday, FL villas
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

50 Villa rentals in Holiday, FL

Our Favorite Vacation Homes with a Pool in Holiday, FL

Dip in whenever you like, as these vacation homes in Holiday, FL come with a swimming pool on-site.

Waterfront Getaway With Pool, Dock & Kayaks - Holiday, FL
Holiday, FL
10/07 – 10/14
$323/nighttotal: $2261 (7 )

Waterfront Getaway With Pool, Dock & Kayaks

3 2
house , New Port Richey
This waterfront residence is situated 21 miles from Pier 60 in New Port Richey, providing a private retreat with direct access to a beach, dock, and kayaks.
This 140-square-foot home offers 3 bedrooms, 2 bathrooms, and accommodates up to 19 guests, featuring a private swimming pool, on-site bar, fitness center, and EV charging station, ideal for families and outdoor enthusiasts.
Waterfront Gulf Getaway - Holiday, FL
Holiday, FL
10/07 – 10/14
$291/nighttotal: $2037 (7 )

Waterfront Gulf Getaway

1 2
house , Beacon Square
This waterfront vacation home in New Port Richey, Florida, offers stunning sea views and is conveniently located 24 miles from Pier 60 and 30 miles from Raymond James Stadium.
The one-bedroom, two-bathroom house features a private pool, fully equipped kitchen with dishwasher, air conditioning, cable TV, and accommodates up to 19 guests, making it ideal for large groups visiting Beacon Square.
Luxe Retreat With Resort-style Pool Backyard - Holiday, FL
10 1 review
Holiday, FL
10/07 – 10/14
$277/nighttotal: $1939 (7 )

Luxe Retreat With Resort-style Pool Backyard

3 2
house , Holiday
This 3-bedroom, 2-bathroom vacation home is located 28 miles from Raymond James Stadium and 29 miles from Busch Gardens, with Pier 60 also within a 19-mile radius.
This 1370 square foot holiday house accommodates up to 8 guests and features a private heated pool, a garden, air conditioning, and free WiFi.
Luxury Tarpon Springs Waterfront W Gulf Access - Holiday, FL
10 2 reviews
Holiday, FL
10/07 – 10/14
$664/nighttotal: $4648 (7 )

Luxury Tarpon Springs Waterfront W Gulf Access

3 2
house , Tarpon Springs
This waterfront villa in Tarpon Springs offers Gulf access and is located 1.4 miles from Sunset Beach, 15 miles from Pier 60, and 25 miles from Raymond James Stadium.
This family-friendly house features 60 square feet of floor area, accommodates 15 guests with 3 bathrooms, and includes a swimming pool, outdoor fireplace, on-site bar, garden, and fitness center.

Best Holiday, FL houses with a kitchen

Tarpon Tides Cottage - Walk To The Sponge Docks & Downtown! - Holiday, FL
10 24 reviews
Holiday, FL
10/07 – 10/14
$239/nighttotal: $1673 (7 )

Tarpon Tides Cottage - Walk To The Sponge Docks & Downtown!

3 2
cottage , Tarpon Springs
This Tarpon Springs cottage offers a prime location, just a 3-minute walk to the historic Sponge Docks and a 15-minute walk to downtown dining and shops.
This 1390 sq ft house accommodates up to 6 guests with 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, a covered porch with a grill, and Roku TVs in all rooms.
Hot Tub & Gas Grill: Port Richey Retreat - Holiday, FL
9.0 1 review
Holiday, FL
06/27 – 07/04
$228/nighttotal: $1596 (7 )

Hot Tub & Gas Grill: Port Richey Retreat

3 2
house , Port Richey
This 3-bedroom, 2-bathroom house is located in Port Richey, Florida, just 27 miles from Pier 60 in Clearwater and 22 miles from Honeymoon Island State Park.
The 1,190 square foot home features a private hot tub, a pet-friendly policy, and a terrace for outdoor dining, perfect for enjoying the Florida weather.
Dream Home In Holiday With Pool & Spa And More - Holiday, FL
Holiday, FL
10/07 – 10/14
$237/nighttotal: $1659 (7 )

Dream Home In Holiday With Pool & Spa And More

3 2
house , Holiday
This holiday home is situated 19 miles from Pier 60, 27 miles from Raymond James Stadium, and 29 miles from Busch Gardens.
This 1740 square foot vacation rental accommodates up to 17 guests and features a private pool, jacuzzi, garden, air conditioning, and a fully equipped kitchen with a dishwasher and microwave.
The Oasis - 2 Private Homes, Pool, And Bbq - Holiday, FL
10 1 review
Holiday, FL
07/03 – 07/06
$516/nighttotal: $1548 (3 )

The Oasis - 2 Private Homes, Pool, And Bbq

5 2
house , New Port Richey
This 2380 sq ft house in New Port Richey offers 5 bedrooms and 2 bathrooms, accommodating up to 19 guests with a private swimming pool, air conditioning, and complimentary high-speed WiFi.
Located in a quiet area, this vacation rental is conveniently situated for exploring downtown New Port Richey and Gulf Coast beaches, with free private parking and an outdoor dining area for guest enjoyment.

Frequently Asked Questions about villa rentals in Holiday, FL

Destinations nearby

Best Holiday, FL houses with air conditioning

The Red Cedar Lakeside Family Retreat - Holiday, FL
Holiday, FL
07/03 – 07/06
$487/nighttotal: $1461 (3 )

The Red Cedar Lakeside Family Retreat

1 2
house , New Port Richey
This Port Richey vacation home offers a private pool and is located 21 miles from Honeymoon Island State Park, 25 miles from Pier 60, and 30 miles from Raymond James Stadium.
This 1-bedroom, 3-bathroom house accommodates up to 15 guests and features air conditioning, a fully equipped kitchen with a dishwasher, and cable TV.
1 Block To Sims Park: Spacious Getaway W/ Balcony - Holiday, FL
Holiday, FL
07/03 – 07/06
$305/nighttotal: $915 (3 )

1 Block To Sims Park: Spacious Getaway W/ Balcony

3 2
house , New Port Richey
This house in New Port Richey is located one block from Sims Park and within driving distance of Honeymoon Island State Park (18 miles) and Pier 60 (22 miles).
This 2920 square foot residence accommodates up to 15 guests with 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, WiFi, and a private balcony.
Canal Front Getaway Poolside Relaxation Fishing - Holiday, FL
Holiday, FL
10/07 – 10/14
$258/nighttotal: $1806 (7 )

Canal Front Getaway Poolside Relaxation Fishing

3 2
house , Holiday
This canal-front vacation home in Holiday is located 17 miles from Pier 60 and 27 miles from Raymond James Stadium, with Busch Gardens and the University of South Florida each 29 miles away.
This 1350 square foot, air-conditioned house accommodates up to 8 guests with 3 bedrooms and 2 bathrooms, offering a private heated pool, a garden, free Wi-Fi, and free private parking.
The Queen Of Port Richey - Holiday, FL
Holiday, FL
07/03 – 07/06
$305/nighttotal: $915 (3 )

The Queen Of Port Richey

1 2
house , Port Richey
Queen of Port Richey, a one-bedroom vacation home in Port Richey, Florida, offers convenient access to Big Cat Rescue (25 miles), Pier 60 in Clearwater Beach (26 miles), and Honeymoon Island State Park (21 miles).
This three-bathroom rental sleeps up to 15 guests and features free private parking, Wi-Fi, cable TV, a fully equipped kitchen with dishwasher and microwave, and a washer/dryer.

Best Holiday, FL villas and beach houses with jacuzzi

Private Tropical Waterfront Sanctuary W Pool, Hot Tub & An Island! Pet Friendly - Holiday, FL
9.2 111 reviews
Holiday, FL
07/03 – 07/06
$410/nighttotal: $1230 (3 )

Private Tropical Waterfront Sanctuary W Pool, Hot Tub & An Island! Pet Friendly

2 2
house , New Port Richey
This New Port Richey home is located right on the waterfront, offering a peaceful escape close to the city's attractions. The property has earned excellent ratings for its cleanliness, location, and overall experience.
The home is a 2-bedroom, 2-bathroom vacation rental with a private pool, hot tub, and island access. Enjoy modern amenities like air conditioning, a fully equipped kitchen, and a balcony with scenic views.
Charming 1-bedroom 1 Bath, 2 Beds Villa In Palm Harbor With Ac Waterfront Lake - Holiday, FL
10 3 reviews
Holiday, FL
07/03 – 07/06
$266/nighttotal: $798 (3 )

Charming 1-bedroom 1 Bath, 2 Beds Villa In Palm Harbor With Ac Waterfront Lake

1 2
house , Palm Harbor
This lakefront villa in Palm Harbor, Florida, offers direct access to Lake Tarpon and is minutes from Clearwater Beach and Tarpon Springs Sponge Docks, with shops and restaurants within walking distance and a public boat launch one mile away.
This 1-bedroom accommodation, ideal for up to 4 guests, features a king bed, a queen sleeper sofa, a full kitchen with stainless steel appliances, air conditioning, and a community swimming pool, providing a comfortable base for exploring the area.
©2026 cozycozy.com