Holiday rentals with a pool in Holiday

4.93 out of 5 average rating, 101 reviews

Home in Tampa

Cozy Tampa Home with Large Heated Pool

“No Cleaning Fee, No Chores” Your family will be close to everything when you stay at this centrally-located home. This home is located 5-10 mins from shopping centers, restaurants, gyms, pet and child daycares, community sport courts, local parks and hospitals. 20-30 mins from Bush Gardens, Downtown, ZooTampa, Tampa Airport, Cruise Port, Ben T Davis Beach, Raymond James Stadium, Hard Rock Casino, Hillsborough State Park and more. Only 1hr 30min from Disney, Universal, Sea World, Lego Park

5 out of 5 average rating, 103 reviews

Coastal Escape: heated saltwater pool & beaches

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

Guest house in Palm Harbor

4.97 out of 5 average rating, 310 reviews

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

Private suite attached to Large house located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower. Access to shared pool and patio, backyard and Sundeck. Room includes refrigerator/freezer, Microwave, Coffee maker, Iron and kitchenette. Bistro set in room. Private entrances to room and patio/backyard. No shared space. Cable TV, Streaming and Wi-Fi . Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

4.98 out of 5 average rating, 132 reviews

Home in Tarpon Springs

Heated Pool, 5 minutes to Beach!

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)

4.81 out of 5 average rating, 199 reviews

Apartment in Palm Harbor

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!

4.99 out of 5 average rating, 134 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

4.97 out of 5 average rating, 71 reviews

Home in Holiday

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

4.94 out of 5 average rating, 100 reviews

Gulf Harbors Vacation Oasis

This lovely Gulf Harbors home with open floor plan & in-ground heated pool is the perfect getaway! Home on canal that leads directly to the Gulf in minutes-amazing view & quiet, safe neighborhood! Perfect home base for shopping, restaurants, kayaking, exploring, & especially Scalloping in Pasco county! This region includes all state waters south of the Hernando – Pasco county line & north of the Anclote Key Lighthouse in northern Pinellas County,& includes all waters of the Anclote River.

Serviced apartment in Spring Hill

4.9 out of 5 average rating, 130 reviews

“Couples Retreat” jacuzzi horses pool Apt 2

Take it easy at this unique and tranquil getaway. This is a one of a kind barndominium with all the luxuries of a paradise getaway. Indulge in the beautiful resort style pool area this is truly a stunning property gated on 6 acres private and secluded. Bike trail access is also included, so bring your bikes for a nice outing. We also have a private fire pit and outdoor dining exclusive to you! 4 horses are also on the property as well as a goat and 2 mini horses connect with nature!

4.87 out of 5 average rating, 128 reviews

Home in Holiday

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.

4.99 out of 5 average rating, 105 reviews

Home in Tarpon Springs

Tropical Pool Retreat in Tarpon Springs

Welcome to our Tropical Oasis, a fancy yet warm and inviting vacation retreat nestled in the idyllic neighborhood of Tarpon Springs, Florida. - Spacious 3 bedroom home for up to 8 guests - Tastefully decorated living area with plush seating and smart TVs - Fully equipped kitchen for meal preparation - Heated saltwater pool with adjustable temperature - Game Room featuring table tennis, dartboard, and foosball - Complimentary bikes for local exploration

4.93 out of 5 average rating, 137 reviews

Home in New Port Richey

Mackarosa Tampa Bay Luxury Pool House

If you are used to traveling in comfort,then this is best choice for you.House after renovation.High ceilings and beautiful decor will give you a pleasant feeling of comfort.The king bed,will give you pleasant sleep after an active day or a long trip.The kitchen has everything.The pool has a solar panel heated.Airport(35 min)Beaches(19min) Smoking in the house and living with animals are prohibited.After each gust the house is disinfected.Enjoy your stay

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Popular amenities for Holiday rentals with a pool

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House rentals with a pool

5 out of 5 average rating, 71 reviews

Home in New Port Richey

Relaxing Beach-Theme Pool Home!

AnthonyRating, 5 stars3 weeks ago

Very nice, feel like Home.

4.94 out of 5 average rating, 66 reviews

Private pool, Golf Cart, Completely Renovated!

StephanieRating, 5 stars1 week ago

We had a wonderful stay! The house was very clean and had everything we needed for the beach and pool. The golf cart was an amazing addition as there are many places to eat in driving distance to the house. Jarrett was very responsive and friendly. Would absolutely stay here again!

4.89 out of 5 average rating, 153 reviews

Your Home away from Home , Nice inground pool.

AlexanderRating, 5 stars1 week ago

stay was fantastic. only things I would have a (complaint) about would be there is nothing to hold onto while getting in the pool and the master bedroom has 1 outlet per side due to no ceiling lights. otherwise absolutely fantastic. Will definitely be staying again.

4.95 out of 5 average rating, 120 reviews

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

IbnRating, 5 stars3 weeks ago

We visited for my son's graduation. The house accommodated us very well. Spacious, clean, plenty of towels. The pool, grill, and fire pit was a plus.

4.96 out of 5 average rating, 85 reviews

Beachy 3 Bedroom Hot Tub and Saltwater Pool

KristiRating, 5 stars2 weeks ago

Exactly as described, very clean and will definitely be staying again in the future, they also have almost every essential you'll need. pool and hottub was a plus

Superhost

4.91 out of 5 average rating, 200 reviews

"Wet Feet Retreat" pool home

AnitaRating, 5 stars4 weeks ago

For my first AIRBNB it was amazing they had everything you could think of and more

4.94 out of 5 average rating, 34 reviews

Home in New Port Richey

★Golden Paradise ★PRIVATE HEATED POOL★GAME ROOM★

AprilRating, 5 stars4 days ago

We had to reserve this home for our employees to work at a job site. All of them enjoyed their time staying there. I recommend anyone to reserve this home. It was great!

Superhost

Home in Holiday

4.76 out of 5 average rating, 25 reviews

Stunning Lakefront & Heated POOL

BrendaRating, 5 stars2 months ago

We really enjoyed Irmas's place. very comfortable. It was close alot of fun things to do or just staying there was nice too. Beautiful patio and fun wildlife to watch. very nice pool. Great for kids and adults.

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Apartment rentals with a pool

4.99 out of 5 average rating, 103 reviews

Seasalt Breeze private unit No cleaning fee

JimenaRating, 5 stars2 weeks ago

We had a good time. The apartment had everything you needed.

4.9 out of 5 average rating, 204 reviews

Very cozy quality condo close to Clearwater Beach

SusanRating, 5 stars3 days ago

Marta is a pro host, she is attentive and quick to address any issues. Things happen and how those things are handled is what makes the difference between an ok experience and a great experience. I would absolutely stay at Marta's place again. Her place is equipped with all that you need to be comfortable and to feel right at home. The place is an excellent value!

Apartment in St. Petersburg

4.92 out of 5 average rating, 158 reviews

Heron's Hideaway- Studio by the bay!

SaraRating, 5 stars2 weeks ago

What a treasure!! Though small, it completely met our needs. Was clean and homey. Ideal location between downtown Saint Pete and the beaches. Loved the view of the water from the balcony. Kids loved the pool.

Superhost

4.81 out of 5 average rating, 152 reviews

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES

KristyRating, 5 stars2 weeks ago

The location was close to the places we attended for a wedding. Host was very informative and provided recommendations of places to go and things to do. We will be repeat guests.

4.93 out of 5 average rating, 120 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

CassandraRating, 5 stars3 weeks ago

We loved our stay! The hosts were great at communicating with us. Very clear instructions. Place was just like the photos. Very enjoyable stay!

Apartment in Redington Beach

4.87 out of 5 average rating, 144 reviews

Royal Orleans at Redington Beach ( Studio 203 )

DanielleRating, 5 stars3 days ago

My husband and I just got back from the Royal Orleans staying in Marina's unit. This is our 2nd trip to the area, and we love more each time. Marina was very responsive, and flexible as they switched our flights a few times. The unit is very clean, very nice bedding, and towels! Towels were nicer then some hotels we've stayed at! Unit had everything we needed for the week!

Apartment in Gulf Island Beach and Tennis Club

4.91 out of 5 average rating, 100 reviews

Florida Breeze

RobertRating, 5 stars2 months ago

loved the area and condo. We had a nice view of the pool, lagoon and Gulf. Condo had everything we needed. We saw dolphins and manatees. All restaurants we tried were great. Mike was a wonderful host and we would love to come again.