Vacation rentals with a pool in Dunedin

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

This unit private vacation rental is located on the property, plenty of space for 5 quest, 2 bedroom, upper bedroom has a half bath, toilet and sink, lower bedroom has a walk in shower with stack washer and dryer. Conveniently located to the downtown & beach. This unit is pet friendly, we allow 1 dog. Wether your dog is or is not a service dog we have the following guidelines no excessive parking clean up after your pet any physicial damage caused by the pet will be subject to reimbursement

LocationValueLong stay

Two modern tiny homes are situated next to each other, featuring a light color palette. Each unit has large glass doors leading to a spacious deck with railings, while lush greenery surrounds the area, providing a natural ambiance.

4.95 out of 5 average rating, 105 reviews

Surf Shack Tiny Home on Pinellas Trail w/ Heated P

Welcome to the Dunedin Tiny House Vacation Rentals! This Vacation Rental property offers daily, weekly or monthly rentals in 4 luxury tiny homes, a 3 bed bungalow & 1 bed cottage. The 6 Units along with a large Heated Pool are all tucked away within a thoughtfully planned, peaceful & wooded lot.... located right on the Pinellas Trail! The front entrance is conveniently located on Bayshore Blvd just north of the crossroad of Wilson. Once you enter the front door of your unit you will enjoy a

ValueFamilyHiking

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.

ValueLocationNearby

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.

LocationFamilyBathroom

4.93 out of 5 average rating, 107 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

Awesome single family inter-coastal waterfront home with boat dock and pool. 1800 square feet of luxury, 3 bedroom, 2 bathroom, sleeps 10 people in beds. Master bedroom overlooking the water and pool with king bed. Second bedroom with 1 queen bed. Third bedroom with 1 queen bed. Living-room has 2 queen pull out beds and a large glass door wall that opens up to the spacious screen enclosed pool patio. Full kitchen, dining room, living room, laundry area with washer/dryer. Dock has deep water.

FamilyLocationGetting around

4.93 out of 5 average rating, 136 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.* *Maximum parking available is 5 vehicles*

ValueFamilyCheck-in

4.93 out of 5 average rating, 100 reviews

Apartment in Dunedin

Owl Nest Townhouse-Walk downtown, new POOL!

Our brand-new construction condo offers everything you’ll need for an enjoyable and comfortable stay in Delightful Dunedin! Steps from the heart of downtown Dunedin, our quaint costal town offers amazing restaurants, shops, parks, breweries, festivals, night life, marina and Blue Jays baseball! Close to Honeymoon and Caladesi Islands and Clearwater Beach-award winning beaches! New heated pool! *As of March 4, 2024 Owl unit has been combined with Osprey unit to make a more spacious condo.

LocationFamilyHospitality

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

FamilyValueAccuracy

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, 183 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!

ValueFamilyNearby

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.

4.92 out of 5 average rating, 132 reviews

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!

FamilyValueAccess

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.

4.96 out of 5 average rating, 135 reviews

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.

LocationFamilyPets

4.99 out of 5 average rating, 128 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 studio, offers complete privacy with a cozy queen bed, sofa bed, and kitchenette. Enjoy the sparkling in-ground pool reserved for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or explore the nearby Pinellas Trail. Enjoy beaches, dining, breweries, and live music minutes away. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.

LocationValueNearby

Popular amenities for Dunedin rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a 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, 141 reviews

Heated Pool Home | Close to Clearwater Beach

LocationValuePool

4.91 out of 5 average rating, 122 reviews

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

FamilyLocationGrill

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, 177 reviews

Coastal Escape: Heated Pool, Playground&Family fun

LocationFamilyKitchen

4.87 out of 5 average rating, 162 reviews

A spacious outdoor area features a heated private pool surrounded by a screened lanai. Lounge chairs are positioned nearby, and a dining set provides a space for meals. Lush greenery is visible in the background, enhancing the tranquil atmosphere.

Home in Tarpon Springs

Pelican House, Game Room, Pool, 5 min to Beach

LocationValueAmenities

The living area features a spacious white sofa and a complementary armchair set. A light wood coffee table sits on a neutral area rug. A large window provides natural light, and a ceiling fan adds to the bright, airy ambiance. A flat-screen TV is mounted on the wall.

4.88 out of 5 average rating, 101 reviews

Magnolia Pool House W/ Luxury Golf Cart

ValueFamilyAccess

4.98 out of 5 average rating, 237 reviews

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

LocationFamilyBeach

4.97 out of 5 average rating, 153 reviews

Clearwater Gem! XL-Pool | Courts & More!

FamilyValueComfort

4.93 out of 5 average rating, 162 reviews

Modern Coastal: Pool, Mini-Golf & Backyard Resort

ValueLocationParks

Condo rentals with a pool

4.89 out of 5 average rating, 209 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

FamilyLocationLaundry

4.98 out of 5 average rating, 188 reviews

Steps to Heated Pool • Near Beaches • Gated Condo

FamilyValueAccuracy

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!

FamilyLocationAccuracy

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

LocationFamilyParks

4.91 out of 5 average rating, 185 reviews

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

LocationFamilyCondition

4.94 out of 5 average rating, 172 reviews

4.99 out of 5 average rating, 133 reviews

Literally: 15 steps to the Pool, GroundFloor Condo

LocationFamilyComfort

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

FamilyValueBeach

4.95 out of 5 average rating, 113 reviews

Condo Conveniently located to Clearwater Beach

ValueLocationAccess

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

FamilyValueOutdoor spaces

4.98 out of 5 average rating, 117 reviews

4.95 out of 5 average rating, 39 reviews

Tiny home in Dunedin

Boutique Tiny House Escape with Pool | Sunny

ValueLocationOutdoor spaces

4.95 out of 5 average rating, 56 reviews

A spacious studio features a king-sized bed with a woven headboard, bedside lamps providing soft illumination. A kitchenette is visible, equipped with wood cabinets and modern appliances. Light-colored flooring and bright walls create a fresh atmosphere, with a canvas showing beach chairs adding a coastal touch.

Condo in Dunedin

Studio King Sunset at Beso Del Sol (Pool/Hot Tub)

ValueLocationComfort

Superhost

A screened-in patio showcases a luxurious saltwater swimming pool, featuring a floating swan-shaped float. The area is paved with stone tiles and surrounded by greenery, with seating arrangements on either side for relaxation. A jacuzzi is visible, offering a peaceful escape.

4.83 out of 5 average rating, 64 reviews

Saltwater Pool, Near MLB Spring Training & Beach!

ValueFamilyAmenities

4.87 out of 5 average rating, 15 reviews

Tuscan Breeze Pool, Beach, Games, Dog Park, Movies

FamilyValueCheck-in

4.75 out of 5 average rating, 83 reviews

A bright and airy bedroom is shown, featuring a spacious bed dressed in soft linens and accent pillows. Natural light filters through sheer curtains, creating a welcoming ambiance. Elements of modern decor can be seen on the walls, enhancing the overall comfort of the space.

Apartment in Dunedin

Seaside Top Floor Condo

ValueFamilyAir conditioning

4.94 out of 5 average rating, 33 reviews

4BR Family Home•Heated Pool•Game Room•Near Beaches

LocationFamilyCheck-in