Vacation rentals with a pool in Palm Harbor

4.97 out of 5 average rating, 135 reviews

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

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

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.

4.98 out of 5 average rating, 80 reviews

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!

Guest suite in Tarpon Springs

A heated saltwater pool is surrounded by lush tropical landscaping, with clear blue water reflecting the sky above. A colorful float rests on the water's surface. The screened enclosure provides a barrier while allowing for views of the serene outdoor space.

4.96 out of 5 average rating, 138 reviews

Private pool suite in heart of Tarpon Springs!

Charming private suite in a safe, serene neighborhood—just minutes from beaches, Downtown Tarpon, Sponge Docks & Sunset Beach! Your cozy retreat features a private entrance, queen bed, fast WiFi, cable television, a full kitchen & heated in-ground pool. Explore Tarpon Springs and the Pinellas Trail on provided bikes, then unwind at Sunset Beach with provided beach towels, chairs, umbrellas, toys, cooler & sunscreen. This space is a perfect blend of comfort, convenience & coastal charm!

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.

4.95 out of 5 average rating, 163 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!

5 out of 5 average rating, 101 reviews

A private backyard pool area is featured, showcasing a clear blue in-ground pool surrounded by lounge chairs and sunbeds with striped cushions. Lush greenery and potted plants add a tranquil touch, while a shaded umbrella stands at one end for comfort.

Guesthouse in Ozona

Private pool, steps to gulf, fishing, bike trails

Escape to your private Palm Harbor oasis! This updated studio features a cozy queen bed, sofa bed, and kitchenette, plus a sparkling in-ground pool reserved just for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or hop on the nearby Pinellas Trail for biking and exploring. Enjoy beaches just minutes away, along with amazing dining, breweries, and live music in historic downtown. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.

A spacious screened-in patio features comfortable seating arrangements with wicker armchairs, designed for relaxation. A circular table sits at the center, accompanied by a fire pit. The saltwater pool glistens in the background, surrounded by tropical greenery and ample natural light.

4.95 out of 5 average rating, 114 reviews

FREE Heated Pool & Spa l Book your Winter Vacation

Bring the whole family to paradise with plenty of room for fun! Enjoy a private heated saltwater pool 💦, nearby beaches 🏖️, and all the space you need in this 5-bedroom home 🏡. Enjoy amenities and games galore 🎯🎲! 📍 **Nearby Beaches:** 🌊 Crystal Beach – 10 min 🌴 Honeymoon Beach – 13 min 🌅 Sunset Beach – 20 min ☀️ Clearwater – 30 min *⚠️ Pool & spa are saltwater and heatable—pool up to 80°F, spa up to 104°F. Temps may vary due to weather.*

A modern kitchen features white cabinetry and sleek stainless steel appliances. A central island with two wooden stools invites gatherings. Natural light spills through a nearby doorway, illuminating decorative greenery and tasteful textures along the walls.

4.99 out of 5 average rating, 148 reviews

Seasalt Breeze - Easy pool access, Free parking.

The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Location is central with short distance to nearby beaches, attractions and other nearby towns. Unit is approximately 500 square feet with a living room-kitchen open concept and One bedroom - bathroom open concept. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport

4.99 out of 5 average rating, 117 reviews

Literally: 15 steps to the Pool, GroundFloor Condo

Unwind at this stunning Complex at Clearwater that resemble a vacation resort, gated community, extremely safe. Don't want to go out? There is everything you need right in the complex: Free Parking, 24/7 Free Gym, steps to the heated Pool with BBQ area and other wonderful-friendly guests for company (if needed), shops and few dining places in walking distance, your private patio to sit, drink, chat and relax; take some time for you!

5 out of 5 average rating, 38 reviews

A charming exterior of a townhome is presented, featuring a bright red front door. Lush greenery and colorful plants frame the pathway leading to the entrance, with a well-maintained lawn inviting guests to explore. The surrounding area is dotted with additional townhomes.

Villa in Fox Chase

Coastal Cottage

Relax with the whole family or a peaceful couples get away. Great little Hideaway with a Large Pool, Club House, Playground for the little one. This cozy town home is 900 sq ft This is a fully furnished unit has everything you need to hide out or venture out to see all Tampa Bay has to offer. Completely renovated tin early 2023 everything was purchased new. Brands Like Macys, Crate and Barrel, My Pillow and others.

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

4.96 out of 5 average rating, 90 reviews

Private pool, Golf Cart, Completely Renovated!

Discover the ultimate retreat in a central location! Golf cart to Down town, restaurants, breweries, parks, and trails! Multiple beaches with-in a 10 minute drive. This thoughtfully equipped home is an oasis of leisure, offering a pool, games, and a fully-equipped kitchen. Optional Golf cart rentals, private boat rides and fishing trips add to the excitement. Book now for an unforgettable experience!

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, 147 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to your private backyard oasis. Relax by the heated pool, grill and dine outdoors, all within a fenced-in space. This home is ideally located—just a short drive to Crystal Beach, minutes from downtown Palm harbor, Dunedin and Tarpon Springs, and bike ride away to Pinellas Trail, golf courses, Honeymoon Island, and Clearwater Beach. Pets are welcome

4.9 out of 5 average rating, 100 reviews

Heated SW Pool - Near Beaches, Golf, Trail & Food

* Heated salt water pool * Honeymoon & Caladesi Island (10min) * Downtown Dunedin & Sponge docks (10min) * Pinellas trail bike/walk/run (2blks) * Walk to restaurants/bars * Innisbrook Golf courses (4miles) * Large patio w/outdoor dining & lounge spaces * Beach chairs, towels & beach toys provided * Cornhole boards & bags provided for extra outdoor fun

Popular amenities for Palm Harbor rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The outdoor area features a heated pool with crystal-clear water, surrounded by a screened lanai. Comfortable lounge chairs are placed nearby, providing ideal spots for relaxation. Tropical plants enhance the space, framing a serene environment perfect for swimming and sunbathing.

4.9 out of 5 average rating, 128 reviews

Heated Pool, 10 min to Beach, Close to Restaurants

4.91 out of 5 average rating, 127 reviews

A private swimming pool is surrounded by a screened patio, with colorful floatation devices resting on the clear water. Lounge chairs are positioned nearby against a bright yellow wall. Natural light floods the area through glass doors, creating a refreshing atmosphere.

Home in Forest Hills

Heated Pool • Near Tarpon & Gulf Beaches 5 mi

4.99 out of 5 average rating, 261 reviews

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

Heated & Screened in Pool-All Essentials Provided

4.79 out of 5 average rating, 135 reviews

A covered swimming pool area features a clear and inviting pool, surrounded by a spacious patio with tiled flooring. Large glass doors allow natural light to flood the space, while lounge chairs are positioned nearby, offering a comfortable spot to relax.

Home in Dunedin

House of Relaxation

4.95 out of 5 average rating, 150 reviews

Home in Dunedin

Dunedin 5 STAR+ Heated Pool+Near Beach

4.96 out of 5 average rating, 375 reviews

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

An outdoor area features a heated pool surrounded by a screened enclosure, providing a bright and airy setting. Comfortable lounge chairs are positioned nearby, with greenery visible outside the enclosure. Natural light filters through the screens, creating a serene space for relaxation.

4.95 out of 5 average rating, 129 reviews

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

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 out of 5 average rating, 136 reviews

Coastal Escape: heated saltwater pool & playground

Condo rentals with a pool

Condo in Independence Square

A private balcony offers a cozy seating area with blue cushions and a small table. Palm trees and beach views are visible beyond the railing, where the sand meets the water, enhancing the relaxing beach atmosphere.

4.9 out of 5 average rating, 124 reviews

Oceanfront View, Spacious Townhouse, Heated Pool

The entrance to the Avalon condo complex is presented, featuring a decorative fountain surrounded by lush greenery and palm trees. A welcoming sign indicates the name of the property. The building showcases a well-maintained façade under a clear blue sky.

4.88 out of 5 average rating, 111 reviews

Amazing main floor condo at Avalon

4.98 out of 5 average rating, 100 reviews

Lovely Condo minutes from beach & King bed

An exterior view of a yellow condo building is depicted, featuring palm trees and shrubs. A pathway leads to a private entrance, while large windows allow ample natural light. The surrounding landscaping creates a welcoming atmosphere in the gated community.

4.96 out of 5 average rating, 134 reviews

Bright and Spacious 1Bed/1Bath condo.

4.94 out of 5 average rating, 133 reviews

The image captures a view from the condo balcony, showing a clear blue sky and the tranquil Gulf of Mexico. The pool area is visible, featuring a large swimming pool surrounded by lounge chairs. Beach umbrellas dot the sandy shore, providing a vibrant contrast.

Condo in Indian Shores

Tropical Beachfront Penthouse-Beach Cottages

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.

4.94 out of 5 average rating, 154 reviews

Beachfront Condo with Centerline Sunsets

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, 125 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

4.99 out of 5 average rating, 209 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.

Other vacation rentals with a pool

A modern kitchen is presented with stylish white cabinetry and a spacious concrete countertop. Two pendant lights hang above the bar seating, which features four black chairs. Stainless steel appliances, including a refrigerator and microwave, are visible, providing a well-equipped cooking space.

5 out of 5 average rating, 56 reviews

Wonderful Condo at Avalon - Fully Renovated

4.94 out of 5 average rating, 50 reviews

The dining area features a modern table with gold accents, surrounded by plush gray chairs. A stylish chandelier hangs above, illuminating the space. The open-concept layout offers a clear view of the adjacent kitchen and a spacious living area with a large television.

Villa in Palm Harbor

Villa Luxe~Heated Saltwater Pool~Near Beaches

4.95 out of 5 average rating, 77 reviews

An outdoor patio area features a shaded table surrounded by four adirondack chairs. A tropical palm tree adds greenery, and a grilling station is positioned nearby. The space is enclosed by a white fence and showcases a well-maintained lawn.

Home in Oldsmar

Sunny Oasis: Villa Retreat

4.89 out of 5 average rating, 57 reviews

A serene outdoor pool area is highlighted, featuring a crystal-clear solar-heated pool. Two lounge chairs are positioned alongside the pool, with lush greenery providing a natural backdrop. A stacked stone waterfall adds a tranquil touch to the secluded space.

Home in Fox Chase

Paradise in Palm Harbor l Free Heated Pool

4.9 out of 5 average rating, 20 reviews

The exterior of a two-story condo is showcased, featuring a well-maintained entrance with a concrete pathway bordered by lush green grass. The building has multiple windows and a combination of beige and brown siding, along with a row of palm trees enhancing the tropical setting.

Apartment in Oldsmar

Cozy Private 2BR FL condo

5 out of 5 average rating, 4 reviews

Home in Clearwater

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

4.73 out of 5 average rating, 11 reviews

Tiny home in Dunedin

Luxury Tiny Home 1 Bed 1 Bath Unit C “Shelly”