Vacation rentals with a pool in Wesley Chapel

4.99 out of 5 average rating, 105 reviews

A heated salt-water pool is enclosed by a screened patio, providing a spacious area for relaxation. Comfortable lounge chairs are positioned nearby, with bright outdoor decor enhancing the inviting setting. Large glass doors open to the interior, allowing natural light to fill the space.

Home in Port Richey

Angelita's Lake Home 3br3ba w/heated pool

+Spacious family retreat on lake +Free heated pool +Huge last-minute discounts +Big deck, BBQ, dining & firepit +Private backyard lakefront +3 bedrooms, 1 king, 1 queen, 2 twin +3 full baths +Easy to cancel +Pet friendly +Fishing +Games +Quiet serene safe +5 minutes to Gulf sunsets +5 min to Sims Park +20 min to Tarpon Springs +39 min to Tampa airport +50 min to Busch Gardens +5 min to restaurants +Fully equipped kitchen +Free parking & garage +Washer-Dryer +Work area +Hi-speed WIFI +Smart TVs

4.97 out of 5 average rating, 116 reviews

A modern single-story home is set amidst lush grass and tropical landscaping. Palm trees frame the structure, which features a clean exterior and large windows. The driveway leads to a two-car garage, enhancing the home’s welcoming curb appeal.

Home in New Tampa

Poolside Paradise Retreat-spacious 4 bedroom home!

Welcome to The Poolside Retreat! Bring the family, unwind, & have fun at our modern Tampa home, located just a short distance away from beautiful downtown Tampa and other local attractions. If you are looking for a spacious place to stay that incorporates the perfect mix of indoor and outdoor fun, look no further. 4 bedrooms to accommodate 8 guests with fully stocked kitchen and outdoor bar/grilling area. Outside you will find a pool (heated during winter), outdoor seating and covered patio.

4.98 out of 5 average rating, 136 reviews

A spacious game room features a blue felt pool table and a foosball table, providing ample entertainment options. The room is well-lit with overhead lighting and includes a wall-mounted television, ensuring a lively atmosphere for games and relaxation.

Home in Lutz

Entire House with Game Room in Lutz - near Tampa

Entire house with a Game Room equipped with a pool table and a foosball table. Designated working area in Master Bedroom. One King Bed, one Queen Bed and two Twin Beds to accommodate a group of up to six people. A TV in each bedroom, living room and game room. Easy access to USF, Busch Gardens, restaurants, malls and beaches. Short distance to Tampa Premium Outlets and Advent Health Center Ice. Playground, Community Pool, Basketball and Tennis Courts are conveniently located across the street.

4.93 out of 5 average rating, 69 reviews

A spacious living area features high ceilings and natural light, with a comfortable seating arrangement that includes a gray sectional and armchairs. A modern coffee table sits at the center, complemented by a decorative lamp and plants. The area seamlessly connects to a dining space with a large table.

Home in Wesley Chapel

Designers Villa @ Saddlebrook

A Beautiful completely remodeled 3 bedroom 3 bathroom villa with pool, in the prestigious 24 hr guard gated community of Saddlebrook Resort in Wesley Chapel FL. Surrounded with mature landscaping, the community boast 2 of Florida's most Picturesque Arnold Palmer Golf Courses & 45 tennis courts. Everything you need for a great stay is here! Tons of area restaurants as well as onsite! Everything is NEW, TV in every room, printer, fireplace & more! You will absolutely love it here!! See you soon!

4.95 out of 5 average rating, 21 reviews

Luxury Airbnb on Wesley Chapel

Luxury Airbnb, If you are looking for a place where you can relax surrounded by nature but at the same time be close to Tampa area this is the right place for you. You are only 35 minutes away from Tampa airport , 15 minutes from Tampa premium outlets and 3 MINUTES FROM EPPERSON LAGOON (one of the biggest attraction in the area to enjoy) This property has a total of 2 bunk beds, 2 queen beds and one king bed . Total guest allowed 12. NO other guest is allowed in the property if not listed.

Guesthouse in Spring Hill

A screened-in pool area is highlighted by a clear blue sky and scattered clouds. The pool, partially covered, is surrounded by light-colored pool decking. Lush greenery and palm fronds frame the scene, providing a relaxing outdoor space.

J&M Homestead

Relax with the whole family at this peaceful place to stay. Close to I-75 and Suncoast Parkway in Pasco County. Located north of Land O Lakes, Florida, in Pasco Trails, a gated community of acreage and horses. Outlet mall, many eating establishments and sports complexes within half-hour drive. We have had to institute a policy of "no smoking. To be clear, we are retired couple who live in the main house. The apartment is attached but has its own entrance and is self contained.

4.99 out of 5 average rating, 198 reviews

4.89 out of 5 average rating, 157 reviews

Home in Land O' Lakes

Delightful elegant lake home

Escape to a hidden slice of Florida paradise where luxury, tranquility, and breathtaking waterfront views create an unforgettable stay. This stunning lakefront retreat in beautiful Land O’ Lakes offers the perfect balance of upscale comfort and peaceful relaxation. Surrounded by serene bird sanctuary views and glowing Florida sunsets, this private getaway was designed for guests who want more than just a place to stay — they want an experience.

A serene pool area is framed by lush greenery, with a clear blue pool inviting relaxation. Gentle steps lead into the water, and a wooden deck extends nearby, offering additional seating. The tranquil view of the lake canal enhances the peaceful atmosphere of the space.

4.97 out of 5 average rating, 141 reviews

Lakeview Retreat with Private Pool Perfect Getaway

Welcome to our charming Tampa retreat! This newly renovated house has been carefully designed with an open layout, it features 2 bedrooms and 2 full bathrooms. The highlight of this home is undoubtedly the patio area, beautiful outdoor furniture, and an amazing pool with a stunning and unique view of the lake canal. The location is perfect, everything is nearby with quick access to major highways such as I-4, I-75, and I-275.

4.89 out of 5 average rating, 184 reviews

Home in Spring Hill

Ranch Pool Resort with Horses jacuzzi nearby park

Take it easy at this unique and tranquil getaway. This is a country setting close to the city of tampa bay on 6 acres gated with every detail in mind Owner maintained ranch style property with 4 horses you will feel at home away from your home trees surround the outer perimeter as well as a huge pool with layout chairs. Take a stroll through the nature walk trail. Experience nature in luxury at this beautiful ranch home!

A welcoming hallway introduces the home, featuring a decorative sign that reads 'Welcome to your Vacation Home.' Soft carpeting complements the hardwood floor, while a dining area is visible at the end, adorned with a table and chairs. Natural light filters through sliding doors.

4.93 out of 5 average rating, 139 reviews

3 Bedroom/2 Bath Home

Nestled in a peaceful and secure community, offering a comfortable and serene environment suitable for both children and adults. The community amenities include a playground for kids, a community pool, and a dedicated dog park. We understand that pets are part of the family and we welcome them to our home with open arms. We kindly request that no parties or smoking take place on the property.

Treehouse in Wesley Chapel

Stilt House & Pool

Experience an authentic Florida Stilt House stay with curated comforts & amenities. Transform market finds into fresh meals in the full kitchen. Reset with nostalgic board games, books, & movie nights as you tuck in after a day of adventure. The treehouse style wrap around porch & the pool loungers invite you to linger. EV charging available (message for details) + Starlink + Roku.

4.95 out of 5 average rating, 100 reviews

A well-maintained pool area is enclosed by a mesh screen, highlighting the clear water and surrounding brick-paved deck. Lush green grass fills the backyard, complemented by a wooden garden border, creating a relaxing outdoor space for guests to enjoy.

4.8 out of 5 average rating, 111 reviews

Red Royalty Pool, King Bed, Yard

Welcome to your perfect getaway! This spacious 5-bedroom, 3-bathroom house offers ample room for family and friends. Enjoy sunny days by the pool or unwind in the comfortable living spaces. With modern amenities and a prime location, this short-term rental promises a relaxing and memorable stay for up to 12 guests. Book now for your dream vacation!

Popular amenities for Wesley Chapel rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A covered patio area features a built-in seating arrangement with soft cushions, accompanied by a round coffee table. The space opens to a sparkling pool surrounded by wooden decking and lush greenery, offering a serene outdoor experience.

4.99 out of 5 average rating, 175 reviews

Hacienda Hideaway w/ heated pool

4.79 out of 5 average rating, 107 reviews

Sunny Oasis Tampa: Heated Pool & Paradise

4.98 out of 5 average rating, 137 reviews

A serene waterfront view captures a canal lined with homes and docks. The still water reflects the soft hues of the sunset, while palm trees and boats add to the tranquil atmosphere.

Home in Town 'n' Country

Canal-front Sanctuary | Manatees, Pool, Hot Tub

A round above-ground pool is surrounded by a gravel space, featuring a sturdy ladder for access. A bright yellow flotation device rests in the clear water, reflecting the sunlight. In the background, modern buildings and trees provide a sense of openness.

4.85 out of 5 average rating, 124 reviews

The day has arrived, enjoy.

4.88 out of 5 average rating, 140 reviews

Enjoy every moment

4.79 out of 5 average rating, 143 reviews

A serene outdoor space features a rectangular swimming pool, surrounded by a spacious paved area. Two chairs are positioned near the pool. A white fence provides privacy, while trees line the background, enhancing the tranquil setting.

Home in Town 'n' Country

Villa Paradise

5.0 out of 5 average rating, 6 reviews

Monthly Stay | Dedicated Workspace | Wesley Chapel

A spacious living area is highlighted by a grey sectional sofa and a wooden coffee table atop a light area rug. The room features high ceilings and archways, with natural light illuminating the space. A flat-screen TV is mounted on the wall across from the seating area.

4.87 out of 5 average rating, 83 reviews

NEW - Poolside Oasis Heated POOL Home - 2000 SF

Condo rentals with a pool

4.84 out of 5 average rating, 169 reviews

A modern living area features a light-colored sofa and dark accent chairs arranged around a central ottoman. A wall clock complements the artwork displayed above the couch, while the kitchen area is visible in the background, showcasing sleek cabinetry and appliances.

Condo in Lutz

Millers, BeOne Naturally Clothing Optional Premium

A comfortable living area is highlighted by a black sofa with decorative pillows and a brown leather armchair. A round mirror adorns the wall, and a coffee table is placed on a patterned area rug. The open kitchen is visible in the background, featuring bar seating.

4.96 out of 5 average rating, 273 reviews

Centrally Located/Pickleball/Pool/Washer/Dryer/Fun

A serene balcony view captures a sunset over calm waters, with silhouetted palm trees in the distance. A small round table with a lantern sits next to a comfortable chair, creating an inviting space for relaxation.

4.95 out of 5 average rating, 386 reviews

Modern Waterfront Condo - Captivating Sunset Views

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.

4.97 out of 5 average rating, 245 reviews

Tiki Themed Waterfront Condo on Tampa Bay

Lounge chairs are arranged on the sandy beach, accompanied by thatched umbrellas providing shade. The calm waters of the bay are visible in the background, and a multi-story building is situated beyond the beach area.

4.86 out of 5 average rating, 142 reviews

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views

4.9 out of 5 average rating, 236 reviews

Top Floor | Mangrove Bayview + Pool at Tampa Bay

4.8 out of 5 average rating, 134 reviews

A living room features a comfortable sectional sofa positioned beside a glass coffee table. Natural light enters through large windows, illuminating a cozy reading area with a rocking chair. The walls display a colorful piece of artwork, and a ceiling fan enhances the airy atmosphere.

Condo in New Tampa

Beautiful and spacious condo centrally located

4.95 out of 5 average rating, 127 reviews

Tampa Bay Waterfront Views Rocky Point

Other vacation rentals with a pool

5.0 out of 5 average rating, 7 reviews

Apartment in Zephyrhills

Condo at Saddlebrook Resort Golf & Tennis.

5.0 out of 5 average rating, 3 reviews

Condo in New Tampa

Pondside Retreat Near USF & Moffitt

4.96 out of 5 average rating, 47 reviews

Villa in Dade City

Cozy Golf Villa at Lake Jovita * St. Leo access

5.0 out of 5 average rating, 16 reviews

Luxury Tampa Oasis: Pool/Spa/Theater/Sleeps12 + EV

Guesthouse in Zephyrhills

My cabin

4.96 out of 5 average rating, 23 reviews

4.96 out of 5 average rating, 27 reviews

Townhouse in Zephyrhills

Stay in our Bright and Beautiful Mirada Home

5.0 out of 5 average rating, 25 reviews

Home in New Port Richey

Richey Suncoast Resort- Pool, Spa & Arcade Oasis