
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.

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

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.

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

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.

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!

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!

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.

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.

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.

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

*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…

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
House rentals with a pool

Tarpon Family Retreat-Heated Pool, Fire Pit & Fun!

River Home with Pool, Sunset, Dolphin & Fishing

Richey Suncoast Resort- Pool, Spa & Arcade Oasis

Coastal Holiday Home w/Pool - Minutes to Beaches

Gulf Harbors Getaway!

Relaxing Beach-Theme Pool Home!

Endless Summer

Florida style home !
Condo rentals with a pool

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

Relax in a Newly Renovated Beach Front Paradise

Ocean Breeze • Easy - Heated Pool Access

Tiki Themed Waterfront Condo on Tampa Bay

Beachfront in exclusive resort

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Florida Breeze

Modern Waterfront Condo - Captivating Sunset Views
Other vacation rentals with a pool

Waterfront Retreat with Heated Pool, Hot Tub&Dock

Gulf Harbors Getaway Home with Pool

Coastal Paradise Waterfront with Dock, Gulf Access

Heated Pool & Spa Oasis Near Clearwater Beach

Holiday Coast Hideaway

Coastal Cottage | Top 1% Airbnb Worldwide

Home with access to the Gulf.

Studio near Anclote River Park
When is the best time to visit Holiday?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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. temp | 17 °C | 18 °C | 20 °C | 23 °C | 26 °C | 28 °C | 29 °C | 29 °C | 28 °C | 25 °C | 21 °C | 18 °C |
Destinations to explore
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- Family-friendly rentals Holiday
- Rentals with a washer and dryer Holiday
- Rentals with a fireplace Holiday
- Rentals with outdoor seating Holiday
- Rentals with a firepit Holiday
- Pet-friendly rentals Holiday
- Rentals with beach access Holiday
- Rentals with lake access Holiday
- Rentals with a patio Holiday
- Waterfront rentals Holiday
- House rentals Holiday
- Apartment rentals Holiday
- Rentals with pools Pasco County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Bean Point Beach
- Amalie Arena
- Tampa Convention Center
- Dunedin Beach
- Vinoy Park
- Hard Rock Casino
- University of South Florida
- John's Pass
- Tropicana Field
- Fort De Soto Park
- Epperson Lagoon
- Sand Key Beach
- Weeki Wachee Springs State Park
- Anna Maria Public Beach
- MidFlorida Credit Union Amphitheatre
- River Strand Golf and Country Club
- Busch Gardens
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park





