Holiday rentals with a pool in Palm Harbor

4.99 out of 5 average rating, 116 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.

ValueLocationLayout

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, 163 reviews

Coastal Escape: Kid-Friendly Pool & Playground

★ Family-friendly Palm Harbor retreat near beautiful beaches - Honeymoon Island: 6 miles away - Clearwater Beach: 15 miles away ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large fenced backyard with playground ★ Outdoor dining area ★ 3 bedrooms with new mattresses - California king size bed - Queen size bed - Kid-friendly room w/ 2 bunk beds ★ Renovated kitchen and bathrooms ★ Open living space for family gatherings and movie nights ★ Toys, games and kid-friendly extras

FamilyValueParking

Guesthouse in Palm Harbor

A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.

4.86 out of 5 average rating, 192 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

FamilyValueTV

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, 174 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!

LocationValueLaundry

4.99 out of 5 average rating, 117 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

Pvt Pool, Free Kayaks, Wlk to Gulf, Fish, Bike Trl

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.

FamilyLocationOutdoor spaces

5 out of 5 average rating, 48 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 Palm Harbor

Coastal Cottage | Top 1% Airbnb Worldwide

★ Ranked Top 1% of All Airbnbs Worldwide! 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.

FamilyValueIndoor spaces

Two cheerful pineapple-shaped cups with straws sit on a tan pool deck beside a rolled towel and sunglasses. In the background, a green patio umbrella provides shade over a table and chairs, while a private pool glistens under the sun.

5 out of 5 average rating, 21 reviews

Salty Tide Getaway: Pool, Games & Beach Vibes

Welcome to Salty Tide Getaway — your renovated oasis in sunny Palm Harbor, FL! Relax in the lounge chairs by the private and fenced pool, grill out on the patio, or unwind in the spa-style bath. Just minutes from beaches, parks, and local dining, this 3 bedrooms, 2 bathrooms escape is perfect for families or friends seeking fun and comfort. Enjoy fast Wi-Fi, smart TVs, a fully stocked kitchen, and cozy coastal vibes throughout. Your Florida getaway starts here!

FamilyValuePool

4.99 out of 5 average rating, 268 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

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

LocationFamilyKitchen

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.

4.94 out of 5 average rating, 126 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.*

ValueFamilyWalkability

4.94 out of 5 average rating, 198 reviews

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

This stylish place is perfect for family vacation or work trip.. all brand new furnishing and appliances.. heated pool and 3 TVs for your enjoyment. The home is also conveniently located near many beaches, honeymoon island 6.9 miles Fred Howard park 11 miles ,Clearwater beach 14 miles ,Tampa and St. Pete . Please check house rules for more info. When you book, please put the exact number of guests that are going to be staying at the property.

LocationValueHospitality

Superhost

The image showcases a private backyard featuring a colorful inflatable bounce house and a green putting green. An outdoor seating area is visible with a stone pathway leading to the fun play areas. The interior offers a modern kitchen and cozy lounge area, highlighted by neutral tones and contemporary furnishings.

4.77 out of 5 average rating, 100 reviews

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.

FamilyValueLayout

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, 136 reviews

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

This stylish place featuring a heated pool upon request is perfect for groups, family vacation or work trip. Has an open layout nice kitchen all furniture and appliances brand new. We are walking distance to Lake Tarpon-Bring your boats and jet skiis! Honeymoon Island is 8.8 miles Tampa, Dunedin Causeway only 7.6 miles . Tarpon Springs sponge docks 5.8 miles .St. Pete & Clearwater beach are not to far by car.

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Popular amenities for Palm Harbor rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 100 reviews

An inviting living room showcases ample seating with a gray sectional couch and plush ottoman. A cozy dining area is visible outdoors, furnished with a table and chairs under a shaded canopy. The sparkling pool, surrounded by lounge chairs, is highlighted by vibrant tropical landscaping.

Home in Dunedin

3BR Oasis | Sleeps 11 | Heated Pool | Ping Pong!

FamilyLocationLayout

A modern single-story house is set on a manicured lawn, featuring a paved driveway and a two-car garage. In front, two colorful chairs are positioned under the shade of mature trees, enhancing the welcoming entrance of the home.

4.83 out of 5 average rating, 52 reviews

Newly Remodeled*3 Beds*Pool*Game Room*10minBeach

ValueFamilyAmenities

4.95 out of 5 average rating, 22 reviews

Home in Ozona

Honeymoon Luxury Residence with Heated Pool &Sauna

FamilyLocationWalkability

4.9 out of 5 average rating, 69 reviews

Paradise in Palm Harbor l Free Heated Pool

LocationFamilyAir conditioning

An outdoor seating area is surrounded by vibrant trees and a white privacy wall. Blue armchairs and a small table are situated on a paved patio, offering a comfortable spot to relax. The screened-in pool area is visible in the background, complemented by a well-maintained backyard.

5 out of 5 average rating, 56 reviews

Beautiful house with pool, fire pit, billiard room

LocationValueCleanliness

A spacious living area is highlighted by a large wall-mounted television displaying vibrant underwater scenes. Two tall planters with decorative branches frame the television. A modern entertainment unit holds an electric fireplace, while a round coffee table sits at the center of the cozy seating arrangement.

5 out of 5 average rating, 15 reviews

2 Bed 2 Bath Remodeled House Palm Harbor

FamilyLocationKitchen

4.96 out of 5 average rating, 48 reviews

Home in Crystal Beach

Casa Tropical - Heated saltwater pool, near beach

FamilyLocationWalkability

A serene outdoor space is illuminated by string lights hanging from trees. A winding stone path leads to wooden steps ascending to a deck. Lush green grass surrounds a picnic table positioned on one side, enhancing the tranquil atmosphere of the lakefront setting.

4.98 out of 5 average rating, 43 reviews

Waterfront Gem Near Clearwater • Swim Spa + Nature

LocationFamilyIndoor spaces

Condo rentals with a pool

4.97 out of 5 average rating, 150 reviews

Condo in Clearwater

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

ValueLocationCleanliness

Condo in Clearwater Beach

A balcony view features two cushioned chairs adorned with pink pillows, overlooking a quiet street leading to the beach. Palm trees and lush greenery frame the scene, while the ocean is visible in the distance. Bright blue skies enhance the coastal atmosphere.

4.99 out of 5 average rating, 187 reviews

Newly Reno Luxury Condo 30 Steps to Paradise

FamilyLocationGetting around

4.97 out of 5 average rating, 224 reviews

A vibrant, themed living area features colorful hanging lamps and intricate wall decorations. Lush greenery is present, alongside a mixture of patterned seating arrangements. Large glass doors open to a balcony, allowing natural light to fill the space and offering a view of the outdoors.

Condo in Tampa

Tiki Themed Waterfront Condo on Tampa Bay

ValueFamilyHospitality

4.9 out of 5 average rating, 232 reviews

A bright living room features a gray couch with colorful accent pillows, positioned next to a coffee table. Large sliding glass doors open to a view of the patio. A rug with intricate designs lies on the floor, complemented by a cozy accent chair.

Condo in Largo

Modern and Cozy Condo 6 Minutes from the Beach !

FamilyLocationIndoor spaces

4.97 out of 5 average rating, 114 reviews

Condo in Clearwater

Bright Clearwater Condo, Heated Pool, Near Beaches

FamilyLocationComfort

4.97 out of 5 average rating, 116 reviews

Condo in Clearwater

Lovely Condo minutes from beach & King bed

LocationValueAccess

Condo in Clearwater Beach

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.9 out of 5 average rating, 463 reviews

Amazing views on beachfront

FamilyValueLayout

4.9 out of 5 average rating, 203 reviews

A serene pool area is surrounded by lounge chairs and palm trees, with a view of the water in the distance. Soft lighting from overhead strings enhances the setting. The pool depth is marked at 5 feet, and a sun umbrella offers shade.

Condo in Dunedin

Sunset Resort Condo – Clearwater Beaches & Bikes

ValueLocationBarbecue

Other holiday rentals with a pool

4.82 out of 5 average rating, 39 reviews

Large home with Heated Pool, Games Room, Bikes

LocationFamilyCleanliness

4.93 out of 5 average rating, 61 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

LocationValueAccuracy

4.89 out of 5 average rating, 9 reviews

Pool, Games & More—Fun for Everyone!

LocationFamilyPool

A spacious living area features a large grey sectional sofa adorned with orange and blue accent pillows. A marble coffee table sits in front, while a ceiling fan is visible above. Light enters through large windows, illuminating the open layout connecting to a dining area.

4.96 out of 5 average rating, 47 reviews

The Coastal Calm - Entire Unit

FamilyLocationLong stay

4.93 out of 5 average rating, 97 reviews

A screened patio surrounds the inviting pool, providing views of the waterfront. Sunlight glimmers on the clear water, and grassy areas border the pool deck. Nearby boat docks are visible, enhancing the serene atmosphere by the water.

Home in Ozona

Luxe Private Waterfront Getaway with Pool in Ozona

FamilyLocationAir conditioning

4.88 out of 5 average rating, 40 reviews

A private pool area is featured, surrounded by a secure wooden fence. Poolside loungers and shaded dining are visible under a green umbrella. Lush palm trees and outdoor lighting enhance the inviting ambiance, making it suitable for relaxation and gatherings.

Home in Ozona

3 miles to Honeymoon Island~ Firepit & Pool

ValueLocationKitchen

A modern two-story home features a balanced façade with white walls and large arched windows. Lush palm trees and landscaped greenery frame the entrance, creating an inviting approach. The dual garage doors provide additional functionality, complementing the home's contemporary design.

4.99 out of 5 average rating, 72 reviews

Luxury Waterfront w/ Private Heated Pool

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