Vacation rentals with a pool in Safety Harbor

4.96 out of 5 average rating, 134 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. Happy holidays from our family to yours

4.88 out of 5 average rating, 145 reviews

3 BR/2B pool home WiFI and Brand new furnishings

Lots to Love about this centrally located Clearwater beauty. This pool home is 25 minutes from the Tampa airport and 15 minutes to famous Clearwater Beach and less than a half hour to downtown St. Pete, not to mention a 10 minute walk to Phillies spring training stadium and minutes by car to hundreds of Shoppes and Restaurants. Enjoy this spacious home with split bedroom plan and brand new furnishings. Sweet dreams on the Casper mattresses. Relax Poolside in the screened lania or by the firepit

4.99 out of 5 average rating, 128 reviews

Villa in Palm Harbor

The Palm Haus • Heated Pool • Near Beach • Games

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.

4.88 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, 102 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.

4.94 out of 5 average rating, 116 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.

A screened-in private pool surrounded by a spacious deck is visible, featuring colorful floatation rings resting on the water. Comfortable seating areas are arranged nearby, with overhead lighting softly illuminating the space. Lush greenery can be seen in the background, enhancing the serene atmosphere.

4.94 out of 5 average rating, 181 reviews

Tropical Getaway w/Heated Pool & King Beds

Welcome to our sun-kissed getaway in sunny Palm Harbor! You'll find a fully stocked kitchen, a private heated pool, and comfortable accommodations for up to 6 guests. Whether relaxing on one of our award-winning beaches, playing a round of golf, or exploring Tampa Bay's fun spots, there's something for everyone to enjoy. Just a quick note: Because of a family member's allergies, we're not able to allow any animals on the property, including ESAs. Thanks so much for understanding!

4.98 out of 5 average rating, 233 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, 131 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, 100 reviews

Popular amenities for Safety Harbor rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A heated pool is surrounded by lush palm trees, providing a sense of seclusion. A stone statue and decorative elements are featured along the pool's edge. Sunlight reflects off the water, creating a serene atmosphere in this private outdoor oasis.

4.99 out of 5 average rating, 169 reviews

Tropical Oasis Retreat w/ Heated Pool

4.85 out of 5 average rating, 188 reviews

Tropical 4BR Escape with a Pool, < 7mi to beaches!

Superhost

The outdoor space features a heated pool surrounded by a smooth concrete deck. Several lounge chairs are positioned nearby for relaxation. Lush landscaping includes palm trees, and soft lighting adds ambiance to the area, creating an inviting environment for leisure.

Home in Oldsmar

Modern & Spacious Retreat with Private Pool!

4.82 out of 5 average rating, 124 reviews

4.93 out of 5 average rating, 134 reviews

FREE Heated Pool & Spa l Book your Winter Vacation

4.91 out of 5 average rating, 200 reviews

Home in Largo

The Oasis - Arcades - Golf & Games - HTD Pool

A spacious outdoor area features a heated pool surrounded by a screened enclosure. Two lounge chairs are positioned beside the pool, and a barbecue grill is visible near the edge, providing an ideal setting for relaxation and meals.

4.85 out of 5 average rating, 140 reviews

Heated Pool Home | Close to Clearwater Beach

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.

5.0 out of 5 average rating, 172 reviews

Coastal Escape: Heated Pool, Playground&Family fun

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, 65 reviews

Safety Harbor Retreat off Main St! Pool & Privacy!

Condo rentals with a pool

4.98 out of 5 average rating, 183 reviews

Steps to Heated Pool • Near Beaches • Gated Condo

4.97 out of 5 average rating, 155 reviews

Spacious Key West Retreat, Fun 2 BR, Resort Pool

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, 181 reviews

A vibrant bedroom features a queen-size bed dressed in coral linens with decorative pillows. Shelves display tropical decor, while a large mirror reflects soft light. A matching dresser and small vanity are positioned against the wall, contributing to a warm and inviting space.

4.86 out of 5 average rating, 105 reviews

Avalon At Clearwater Friendly 2 Bedroom

Condo in Clearwater Beach

A private balcony is seen featuring two white chairs and a table, offering uninterrupted views of the Gulf of Mexico. The calming blue sky meets the horizon, enhancing the serene beachfront experience.

Beachfront in exclusive resort

4.91 out of 5 average rating, 336 reviews

The spacious living area features a comfortable sectional couch and a gray recliner. A coffee table sits atop a decorative rug. Natural light enters through windows adorned with soft curtains. A dining table for six is positioned nearby, adding to the inviting atmosphere.

4.86 out of 5 average rating, 209 reviews

Charming Condo Minutes From Gorgeous Beaches

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

A welcoming entrance to The Avalon features a landscaped roundabout with manicured greenery and vibrant flowering plants. A central fountain adds a serene element, while the building's architecture is framed by palm trees and blue skies.

4.95 out of 5 average rating, 112 reviews

Condo Conveniently located to Clearwater Beach

Other vacation rentals with a pool

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, 113 reviews

4.99 out of 5 average rating, 275 reviews

A tranquil lagoon pool is surrounded by lush tropical foliage and colorful flowers. A shaded seating area is visible, along with a light-colored house in the background. Multiple palm trees contribute to the serene atmosphere of this private oasis.

Apartment in Dunedin

Tropical Paradise

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, 25 reviews

An open living area features a high ceiling with a ceiling fan and elegant light fixtures. A large flat-screen television is mounted on a stone wall, surrounded by large windows. Comfortably arranged sofas invite relaxation, alongside a stylish coffee table and a view towards the kitchen.

4.95 out of 5 average rating, 22 reviews

Special vacation house

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

5.0 out of 5 average rating, 14 reviews

Sunlit Escape • Pool • Perfect for Big Groups

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