Vacation rentals with a pool in Holiday

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Holiday

  • Total vacation rentals

    Explore 40 vacation rentals in Holiday

  • Nightly prices starting at

    Holiday vacation rentals start at $42 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,520 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Holiday vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Holiday rentals

  • 4.6 Average rating

    Holiday stays receive an average rating of 4.6 out of 5 from guests

Top-rated rentals with a pool in Holiday

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
Guest favourite
Home in Holiday
5 out of 5 average rating, 16 reviews

Dream Home in Holiday with POOL & SPA and More

Dream home in Holiday with POOL & SPA,This beautifully remodeled 3-bedroom, 2-full-bathroom residence offers modern and comfort. Key Features, Updates: Benefit from recent upgrades, including a new roof , kitchen, appliances, Bathrooms, Doors and fresh paint . Step into stylish luxury brand new luxury vinyl wood flooring. Outdoor Oasis: Relax in your fully Pcv fenced backyard with your pool and spa. The jacuzzi and the Pool is Not Heated, Pet Allow (Only ONE)with a fee $100 Please ask you host

Superhost
Home in Holiday
4.91 out of 5 average rating, 11 reviews

Coastal Family Escape w/Private Pool•Near Beaches

Slip into vacation mode in this bright, newly renovated home just minutes from Gulf Coast beaches and the Tarpon Springs Sponge Docks. Plenty of shopping and restaurants nearby. With 2 living rooms, there’s space for movie nights, games, and foosball. Step outside to your private oasis with a heated pool, outdoor dining, and a BBQ grill. Whether you're exploring the famous Sponge Docks, hitting the beach, or simply soaking up the sun at home, this retreat makes every moment feel like vacation.

Guest favourite
A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.
Home in Holiday
4.96 out of 5 average rating, 104 reviews

Paradise!Renovated waterfront pool home.Sunsets!

No hurricane damage!Sunsets to die for! Completely remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard &sometimes you can spot dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops.New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys that you can take to the beach.Bonfire pit.Grill.Heated pool for a fee. Come,relax&enjoy

Top guest favourite
A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.
Home in Port Richey
4.99 out of 5 average rating, 286 reviews

Heated & Screened in Pool/Coffee Bar/Fully Stocked

🏡 Private Pool House with Large Covered & Screened-In Porch Relax and unwind in this inviting private pool home, featuring a large covered and screened-in porch—perfect for enjoying the outdoors without the bugs. 🌊 Heated Pool Take a dip in the private pool, heated year-round with an electric heat pump (weather permitting), offering comfort no matter the season. Whether you're sipping coffee on the porch or enjoying a swim, this cozy retreat is ideal for a peaceful and private getaway.

Superhost
Home in New Port Richey
4.89 out of 5 average rating, 105 reviews

River Side Home. Three mins to Downtown.

Cozy apartment for family vacations completely renovated, The SIDE RIVER HOME is very close to downtown, restaurants, bars, boat ramp and walking park overlooking the river, beaches, a few miles from Tarpon Spring Sponge Docks , located 20 mins from Fred Howard Park, if you want to kayak and Canoe the perfect place is Weeki Wachee, just 35 minutes from the house , clearwater beaches are for 42 mins, ahh if the passion is the parks we have Busch Gardens only 52 mins away . PETS ARE WELCOME!

Top guest favourite
The charming guest house exterior is framed by a lush green lawn. A walkway leads to a welcoming front door, with two comfortable chairs positioned by the entrance. Large windows allow natural light into the space, complemented by a well-maintained garden area.
Guesthouse in Palm Harbor
4.98 out of 5 average rating, 102 reviews

New Guesthouse with Pool in Palm Harbor

This Brand new Beautiful Guest house was completed in August 2024 and is located in the back corner of a 1/2 acre lot with all the amenities for a short stay or longer stay. From private access to the house and use of the shared pool and patio this house has it all! Full Kitchen, Dining Area, Living room, Washer and Dryer. Stunning Master Bedroom, Master Bath with Dual Vanity, Jacuzzi and walk in shower and spacious master closet. This Gem includes all the amenities for a Luxurious Stay!

Top guest favourite
A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.
Home in Tarpon Springs
4.96 out of 5 average rating, 383 reviews

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

This home is ideally located near Florida's beautiful Sunset Beach and Howard Park Beach - only 17 miles from Clearwater Beach. Take a short ride to world famous attractions like Disney, or Busch Gardens. Don't settle for a hotel when you and your guests can enjoy a home with a gas grill, multiple patios, large kitchen/family room, a large 4K TV and a private jacuzzi/pool with gas heater *option. It's a perfect place for creating family memories or getting together with old friends.

Guest favourite
A view of Lake Conley is depicted, showcasing calm waters under a clear blue sky. Lush trees line the shore, with a walkway and dock visible on the left, offering access to the water. The scene reflects a tranquil outdoor environment.
Home in Holiday
4.87 out of 5 average rating, 135 reviews

Waterfront, Sunsets & Heated Pool & Pet Stay Free!

Close to the beach, family activities, public transport, and the Tampa Airport. You’ll love my place because of the ambiance, the outdoors space, the water view, & the sunsets, PRIVATE Heated pool and VERY comfy beds! I provide fishing poles, tackle box My place is great for everyone and furry friends (pets) too!. Third bedroom is Florida room with sliding glass door. Two twin beds and desk. dinning table. Let me know about your pets. Your pets stay free. Totally fenced yard.

Guest favourite
A fenced backyard overlooks a peaceful lake, with a dock visible along the water's edge. The backdrop features several homes lining the opposite shore, while scattered clouds float in a blue sky above. Green grass and white stones enhance the outdoor space.
Home in Holiday
4.96 out of 5 average rating, 23 reviews

Lake House in Holiday!

3 BRs, 2 Full Baths + Queen Sofa Bed Peaceful lakefront home on Lake Conley. The backyard has lake access with a dock and space to entertain. Stunning views of the lake and includes an above ground pool to cool off on those hot days . 8 foot pool table (inside).Only a few miles away from tourist attractions (Tarpon Springs, beaches, Newport Richey), 30-45 minutes from Tampa International Airport & Clearwater Beach depending on traffic. 25-30 minutes from Dunedin.

Superhost
Home in New Port Richey
4.4 out of 5 average rating, 5 reviews

Tropical Paradise

Enjoy a stylish experience at this centrally-located place.Tropical Paradise is a cozy vacation home located near Tarpon Springs and just minutes from beautiful beaches. The home features two comfortable bedrooms, a private pool, spacious concrete parking, and an outdoor kitchen perfect for BBQs and gatherings. Ideal for families or couples seeking relaxation, privacy, and a peaceful tropical setting to enjoy the Florida sun and create unforgettable memories

Guest favourite
A light-filled living area features a spacious sectional sofa and a wooden table with a decorative chair. Natural light streams in through large windows with shades, illuminating the neutral color palette and coastal-inspired decor, creating a relaxed environment.
Home in Holiday
4.95 out of 5 average rating, 80 reviews

*NEW* Riverside Retreat w/Pool

Take it easy at this unique and tranquil getaway. Welcome to our Riverside Retreat where you will enjoy incredibly relaxing peaceful days, and sunset views. Recently renovated 2 Bedroom, 2 Full Bathroom, pool home with dock and privacy fenced backyard on the Anclote River. This home is fully equipped and is ready for you to enjoy. Conveniently located and only a 9-minute drive to the World-famous Sponge Docks and minutes from our award winning beaches…

Guest favourite
Home in Holiday
4.88 out of 5 average rating, 52 reviews

Heated Pool, Hot Tub & Sand Volleyball

Your perfect getaway awaits in this pet-friendly 2BR/2BA retreat! Relax by the in-ground pool and hot tub, play a game of sand volleyball, unwind on the deck or have a BBQ. The fully fenced yard offers privacy, while the covered outdoor seating, pool-side hammock, fire pit, and a variety of games make it fun for all. With WiFi, AC, and a workspace, it’s perfect for both short and long stays. Just minutes from the beach, dining, and entertainment.

Popular amenities for Holiday rentals with a pool

When is the best time to visit Holiday?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$239 CAD$281 CAD$303 CAD$278 CAD$237 CAD$253 CAD$253 CAD$236 CAD$197 CAD$211 CAD$232 CAD$258 CAD
Avg. temp17 °C18 °C20 °C23 °C26 °C28 °C29 °C29 °C28 °C25 °C21 °C18 °C
  1. Airbnb
  2. United States
  3. Florida
  4. Pasco County
  5. Holiday
  6. Rentals with pools