Vacation rentals with a pool in Safety Harbor

4.99 out of 5 average rating, 133 reviews

Villa in Palm Harbor

Palm Haus • Heated Pool • Near Beach • Game Room

Charming home with stylish baths & bedrooms. Heated pool included in the price. Gas fire-pit, outdoor games, large secluded backyard! Game room! Near Honeymoon Beach & Caladesi Island open for sunbathing & water sports; historic downtown Dunedin with cute shops, cafes, restaurants & cultural events. The area has a number of top-notch golf courses and trails. Palm Harbor's welcoming community & mild climate make it an ideal getaway for outdoor adventures, cultural experiences, and coastal views.

4.97 out of 5 average rating, 153 reviews

Clearwater Gem! XL-Pool | Courts & More!

Welcome to The Quazzi House, a private ½-acre tropical escape designed for fun, relaxation, and unforgettable memories. This unique 4BR / 3BA home features a 40-ft pool, private hot tub, pickleball & basketball court, and a spacious backyard perfect for families and groups. 📍 15 min to Clearwater Beach 📍 20 min to Tampa 📍 10 min to PIE Airport Ideal for large families or groups looking for an active, resort-style stay in sunny Fl! NO PARTIES — $1,000 fine & cleaning fee strictly enforced!

4.88 out of 5 average rating, 125 reviews

Modern Paradise home near Clearwater Dunedin Beach

Welcome to Safety Harbor house Florida . Close to downtown main street,fun shops,restaurants ,fishing pier water front park and family friendly activities. the home sleeps 6 guests. Has a nice pool and it is great for couples ,solo adventures,business travelers,families with kids .Fully equipped brand new kitchen brand new bedrooms. Wifi TV Alexa. Tampa international airport 15 minutes Clearwater Beach 15 minutes Palm Harbor tarpon springs sunset beach 10 minutes Saint Petersburg 15 minutes.

4.99 out of 5 average rating, 100 reviews

Guesthouse in Dunedin

Dunedin private pool oasis-Cozy Coastal Cottage

100-5★ reviews! Cozy Coastal Cottage is your private tropical escape just 2 blocks from Dunedin’s Main Street. Relax by the sparkling pool, then walk to restaurants, breweries, shops, the marina, and Pinellas Trail. Located in the historic district, you’re minutes from top-rated beaches and the Blue Jays stadium. Enjoy a full kitchen, walk-in shower, fast Wi-Fi, A/C, laundry, and beach gear for the perfect Gulf Coast getaway. Pool days, sunset walks, and downtown nights - all waiting for you.

The exterior of a single-story house is presented, featuring a two-car garage and a well-maintained lawn. Lush green shrubs frame the entrance, and a small American flag is placed near the mailbox. A partly cloudy sky adds depth to the welcoming scene.

4.89 out of 5 average rating, 103 reviews

Nice Sparkling Clean Home with Pool.

Spacious family-friendly retreat. Three comfortable bedrooms and a cozy sitting room within the Master Bedroom, our home offers ample space for the entire family. With two full bathrooms, everyone can enjoy their own privacy and convenience. Step outside to the inviting pool area with a spacious enclosed patio. A Fully stocked kitchen is equipped with everything for preparing and enjoying delicious meals together. Plate settings for six to a comprehensive array of utensils and pots/pans.

4.93 out of 5 average rating, 123 reviews

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

Welcome to Clearwater Tranquility- Our unique space offers endless amenities and fun! With over 5000sq ft there's room for the whole family to enjoy. Most rooms have a view of the yard &pool! Inside includes a movie theatre, 3 dining spaces, 2 living rooms, 2 primary bedrooms, game room, yoga studio,arcade games, home gym/sauna and a wet bar to make your favorite cocktails or juices. Outside presents an Olympic sized swimming pool, pickle ball, mini golf, outside dining, fire pit &more

4.73 out of 5 average rating, 117 reviews

A serene backyard is featured, highlighting a sparkling pool surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. Lush artificial grass complements the outdoor space, while wooden fencing provides privacy.

Home in Oldsmar

Private Pool Home Near Clearwater & Tampa

Only 25 minutes from Clearwater Beach and Tampa, 33 minutes from Buch Gardens, 1.5 hrs from Disney, 18 minutes from Tampa International Airport. This house is completely renovated with a lot of space for you, family and/or friends. The entire house for you and your family. We have a beautiful pool with a Grill for your convinience and a garage for your car. 3 bedrooms for up to 7 persons. A 65" TV in the living room. Wi-Fi. The house has everything you need to have a relaxing time.

4.98 out of 5 average rating, 237 reviews

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

4.92 out of 5 average rating, 132 reviews

A screened-in outdoor area features a heated pool and spa accompanied by a spacious dining table set for eight. Vibrant glassware and dining plates are arranged, capturing bright colors against the backdrop of lush greenery and a clear sky.

Home in Dunedin

Luxury home ~ Heated pool, hot tub, TWO kitchens

Welcome to this stunning 5-bedroom home, located in a quiet, family-friendly neighborhood, just minutes from quaint Downtown Dunedin and a short drive to both Clearwater Beach and Honeymoon Island Beach! 5 bedrooms, 3 bathrooms - including a full "in-law" suite downstairs with it's own full kitchen and living room! It's everything you need and more ♡ Enjoy a heated pool (84°), hot tub, BBQ grill... need we go on? Feel free to ask any questions. We look forward to hosting you!

Vacation home in Safety Harbor

Heated Pool • 4BR • Near Clearwater Beach

Welcome to your private Safety Harbor getaway—perfect for families and groups of up to 8. Enjoy 4 comfortable bedrooms, 2 baths, a private heated pool maintained around 86°F, fast Wi-Fi, a fully equipped kitchen, spacious living areas, and free driveway parking. About 15–20 minutes from St. Pete–Clearwater Airport, 20–25 minutes from Tampa International Airport, and convenient to Clearwater Beach, shopping, dining, and local attractions. Easy self check-in with a smart lock.

4.84 out of 5 average rating, 101 reviews

4.96 out of 5 average rating, 135 reviews

A serene outdoor space features a heated pool, reflecting the colorful sky during sunset. Strands of lights are draped above, enhancing the inviting atmosphere. Comfortable loungers are placed beside the pool, with dining areas visible in the background, surrounded by lush greenery.

Home in Dunedin

Heated saltwater pool|Spacious 4BR/3BA|

Welcome to Cerulean Cottage, our coastal home centrally located in Dunedin, Florida. Whatever brings you to this area, you will find yourself right at home in our comfortable beds, cozy couch, and functionally designed spaces. Have a blast in the pool and game room and wind down in our new 4D massage chair. We are close to conveniences, including grocery stores and many favorite local restaurants and just a short drive from our quaint downtown and beaches.

4.78 out of 5 average rating, 107 reviews

Home in Palm Harbor

Chic|Pool|PuttingGreen|Beaches

Enjoy a relaxing family getaway in the Sunshine State! Spend days relaxing on the beach and enjoying outdoor fun for the whole group with a bounce house, putting green, and more at this stylish home. Whether you’re traveling with family and friends or on business, this is a great place to discover the beautiful. Clearwater Beach area. 8 Min Walk to Saint George Lake 12 Min Drive to Wall Springs Park 22 Min Drive to Clearwater Beach.

Popular amenities for Safety Harbor rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 179 reviews

Pool, King Bed, & Outdoor Kitchen - Near Beaches!

4.93 out of 5 average rating, 136 reviews

Home in Palm Harbor

FREE Heated Pool & Spa l Book your Winter Vacation

5.0 out of 5 average rating, 177 reviews

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

Home in Palm Harbor

Coastal Escape: Heated Pool, Playground&Family fun

4.88 out of 5 average rating, 147 reviews

Hot Tub, Heated Pool, Minutes to Clearwater Beach

4.95 out of 5 average rating, 150 reviews

Artsy oasis in Clearwater

A vibrant pool area features playful tiger floaties and white spherical decorations floating on the surface. The pool is surrounded by comfortable lounge chairs and hammocks, with colorful drapes leading to the entrance of the house. Lush greenery and palm trees add a lively touch.

4.9 out of 5 average rating, 236 reviews

Clearwater GLAM | Pool, Games, Hot Pink Oasis!

An outdoor area showcases a screened-in lanai with a cozy seating arrangement. A wooden table holds decorative items, positioned next to a heated in-ground pool, surrounded by lush greenery and a privacy fence. Sunlight filters through palm leaves, creating a serene atmosphere.

4.97 out of 5 average rating, 66 reviews

Safety Harbor Retreat off Main St! Pool & Privacy!

5.0 out of 5 average rating, 8 reviews

Quiet Safety Harbor Retreat Near Clearwater Beach

Condo rentals with a pool

4.98 out of 5 average rating, 188 reviews

Steps to Heated Pool • Near Beaches • Gated Condo

Superhost

A spacious living room is furnished with a large sectional sofa and a coffee table. A 50-inch smart television is positioned on a white console. Sunlight enters through the large window covered with sheer curtains, and glass doors lead to a balcony with outdoor seating.

4.8 out of 5 average rating, 171 reviews

☼ SUNNY CONDO MINUTES FROM GORGEOUS BEACHES

Condo in Clearwater Beach

A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

4.98 out of 5 average rating, 183 reviews

Condo in Clearwater Beach

An all-season pool is featured on the fifth floor, surrounded by a white railing. The turquoise water reflects sunlight, while lounge chairs are positioned nearby. The bright blue sky serves as a backdrop, enhancing the overall inviting setting.

New! Condo in exclusive Avalon Club

4.91 out of 5 average rating, 185 reviews

4.89 out of 5 average rating, 104 reviews

It’s a "Shore" Hidden Gem, Vacation's Elixir

A cozy bedroom is illuminated by natural light streaming through large windows adorned with patterned curtains. A spacious bed is dressed with floral bedding, accompanied by decorative pillows. A bedside table holds a lamp, and a framed art piece enhances the calming atmosphere, with the pool view visible outside.

4.94 out of 5 average rating, 132 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

4.95 out of 5 average rating, 113 reviews

Condo Conveniently located to Clearwater Beach

Condo in Clearwater Beach

A panoramic view captures the beach at sunset, showcasing soft white sand and tranquil turquoise waters. The sun sets gently on the horizon, casting warm colors across the sky and illuminating the landscape.

Beachfront Condo with Centerline Sunsets

4.94 out of 5 average rating, 172 reviews

Other vacation rentals with a pool

4.96 out of 5 average rating, 204 reviews

An outdoor tiki hut porch is illuminated by soft string lights. Comfortable seating creates a cozy gathering area, surrounded by lush greenery. A wooden dining table sits in the center, offering a relaxed space for meals or conversation.

Guesthouse in Dunedin

Tiki Hut Cottage

Guesthouse in Palm Harbor

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 with Pool in Palm Harbor

4.98 out of 5 average rating, 117 reviews

Townhouse in Safety Harbor

A living area is shown with a light-colored tiled floor and soft blue walls. A spacious gray sofa is positioned beside a simple wooden table with benches, and double glass doors lead to an outdoor seating area.

The Lizard Lair

5.0 out of 5 average rating, 26 reviews

5.0 out of 5 average rating, 32 reviews

Luxe Harbor Haven: 5 bd Near Beaches, MLB + Golf

Bungalow in Safety Harbor

A heated pool is enclosed by a secure childproof cage, surrounded by lush greenery. Soft sunlight reflects off the turquoise water, creating a serene outdoor retreat. A small patch of grass and garden area is visible beyond the pool area.

Retreat off Main Street

4.91 out of 5 average rating, 34 reviews

5.0 out of 5 average rating, 6 reviews

Cottage in Safety Harbor

2A Newly Renovated 1/1 at Coastal Cottages

The living area features an open floor plan with a spacious sofa and a large TV for entertainment. Soft lighting enhances the atmosphere, while art pieces adorn the walls. Large windows provide natural light and views of the connected outdoor deck.

4.95 out of 5 average rating, 44 reviews

Safety Harbor Townhome | Pool & Fenced Yard

An outdoor space is showcased, featuring a manicured lawn bordered by pathways and illuminated by string lights. A screened patio encloses a heated spa pool, while lounge chairs are positioned nearby, creating a welcoming area for relaxation and enjoyment.