Holiday rentals with a pool in Holiday

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Holiday

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

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Guest favourite

Home in Dunedin

4.93 out of 5 average rating, 119 reviews

Everything you'll need, plus! Park Model RV

A relaxing and open space great for beach lovers, cyclists, and people who love the outdoors. This cozy setting provides all the necessities for daily living, plus more to make for a great get away! Accommodates up to four. Within 2 miles of Honeymoon Island State Park and Caladesi Island. Easy drive to Clearwater Beach, St. Pete's Airport and surrounding areas. Short walks to town, bike trails and beautiful Gulf coast sunsets make this a perfect getaway or home base for exploring the area.

26 Sep – 3 Oct

$184 NZD per night

Guest favourite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 200 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower, Double sink Vanity. Access to Patio, Swimming Pool , Backyard and Sundeck. Room includes small refrigerator/freezer, Microwave, Coffee maker, Espresso, Iron and much more. Bistro set in room. Private entrances to room and patio/backyard. Cable TV, Netflix and Wi-Fi included. Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

26 Nov – 3 Dec

$233 NZD per night

Guest favourite

Home in Tarpon Springs

4.98 out of 5 average rating, 110 reviews

Heated Pool, Close to Beaches!

Welcome to Tarpon House Florida, located in the exclusive and historic Tarpon Springs. Our home is a tropical oasis. Perfect for families, couples, and anyone who needs the space to spend time together or enjoy some privacy for enjoyment and relaxation. 10% discount for Military, First Responders, Teachers, friends and family - book & message me, I'll apply the discount, that's it! Completely renovated with all new furniture. Link to 3D Tour of the house is in my guidebook (under my profile)

4–11 Apr

$838 NZD per night

Guest favourite

Guest suite in Tarpon Springs

4.95 out of 5 average rating, 107 reviews

Private suite in heart of Tarpon Springs!

House centrally located in a safe, residential area. Enjoy a clean, cozy & comfortable private suite with private entrance! Next to Downtown Tarpon, Tarpon Springs Sponge Docks, Sunset Beach, Safety Harbor, and many other attractions. Less than 5 minutes from the beach! Enjoy fast wifi, cable, and a cozy queen bed! Full kitchen. During your stay you’ll have access to bicycles, plenty of beach towels, hats, beach toys. Beach chairs, chairs umbrellas, small cooler and a variety of sunscreens

12–19 Jul

$215 NZD per night

Guest favourite

Condo in Palm Harbor

4.8 out of 5 average rating, 155 reviews

Lakeside 2- Bed Apartment Near Clearwater Beaches

Ideally located on Florida's Gulf Coast minutes from many of America’s best beaches. The apartment is situated on the shores of beautiful Lake Tarpon, just north of Clearwater. The big exciting city of Tampa is just 30 mins away with the big theme parks in Orlando only 90 mins away. The pool & jacuzzi are also by the water & decking. Come stay, relax & recharge your batteries in a comfortable peaceful setting yet close by you have all the activities & amenities that you could ever wish for!

31 Aug – 7 Sep

$214 NZD per night

Guest favourite

Condo in Redington Beach

4.97 out of 5 average rating, 457 reviews

AmazingBeachCondo/NoCleaningFee/AwesomeAmenities

Welcome to our condo. We have provided you with just about everything you need to come and vacation at this amazing beach area. The condo is right by the heated pool and a 2-minute walk to the beach. The complex has high-speed internet throughout and a laundry facility. Shopping/Grocery/Pharmacy are all close by. Restaurants/bars very close by. This is an amazing area of Florida, with so many things to see and do. You will love it here. We have also provided bikes for your use to get around.

23–30 Dec

$228 NZD per night

Superhost

Home in Holiday

4.9 out of 5 average rating, 105 reviews

Fun, Spacious and Modern Waterfront Pool Home

This waterfront pool home is the perfect place to relax and enjoy the Florida lifestyle! The entire home was completely updated in 2020 with a mid century modern style. Everything is new from the floor to the ceiling! Enjoy the gorgeous sunsets from the pool or jacuzzi. Kayak the canals and lakes filled with manatees, sting rays, fish and sometimes even Dolphins! Throw a line in off the dock and catch dinner, or release and catch again. 3 Bedrooms and 3 Bathrooms sleeps 6 comfortably.

2–9 Mar

$543 NZD per night

Superhost

Home in Port Richey

4.85 out of 5 average rating, 130 reviews

Penwood Pool Villa

If our dates are open, the house is ready for you, you don’t need to confirm with us. Instant book! PRIVATE POOL! 5 min from kayak trail 15 min from Sun West Beach 25 min from Weeki Wachee Springs 25 min from Tarpon Springs 30 min from Honeymoon Island 45 min from Busch Gardens 50 min from Downtown Tampa Riverwalk 50 min from Clearwater Beach 40 min from TD Ball Park 50 min from Three Sisters Springs Our backyard is fully equipped with Grill, hammock, outdoor seating and lighted pool!

7–14 Oct

$345 NZD per night

Guest favourite

Guesthouse in Spring Hill

5.0 out of 5 average rating, 110 reviews

J&M Homestead

Relax with the whole family at this peaceful place to stay. Close to I-75 and Suncoast Parkway in Pasco County. Located north of Land O Lakes, Florida, in Pasco Trails, a gated community of acreage and horses. Outlet mall, many eating establishments and sports complexes within half-hour drive. We have had to institute a policy of "no smoking. To be clear, we are retired couple who live in the main house. The apartment is attached but has its own entrance and is self contained.

20–27 Sep

$254 NZD per night

Superhost

Home in Holiday

4.88 out of 5 average rating, 110 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.

18–25 Jul

$451 NZD per night

Guest favourite

Guest suite in Hudson

4.91 out of 5 average rating, 143 reviews

UVlite sanitized guest suite w/private entrance.

Our 300 square foot guest suite is good for couples and solo adventurers. It offers many amenities for a small space. Step outside to enjoy the patio, pool and gazebo! Great location for those wanting to experience Florida's nature coast, but still be close enough to everything the Tampa Bay area has to offer at a reasonable price. For the safety of our guests, in addition to extensive cleaning and disinfection I am also using a UV/ozone sanitizing light before guests arrive.

25 Sep – 2 Oct

$132 NZD per night

Superhost

Guest suite in New Port Richey

4.91 out of 5 average rating, 110 reviews

Tropical Suite on Treasure Island’s Bayou NPR

Located in a quiet neighborhood on Treasure Island in NPR. This is a beautiful waterfront vacation rental for two... Enjoy a romantic evening on your private, covered balcony after a day of lounging poolside or fishing and kayaking from the backyard. Being west of 19 and close to Main St, we are in walking distance of all of the fun events in New Port Richey. We hope that you have some time to enjoy the local restaurants, pubs, and events in Downtown New Port Richey!

20–27 Oct

$252 NZD per night