Vacation rentals in Wesley Chapel

Home in Indian Rocks Beach

An above-ground heated pool is surrounded by a stylish wood-paneled enclosure. Bar stools are placed along one side of the pool, providing a space to relax. Shade is provided by an overhead sail, and lush greenery enhances the backyard atmosphere.

4.99 out of 5 average rating, 169 reviews

Luxe BeachHouseA Heated Pool, 2 min walk to Beach

Welcome to your home away from home.Sand,sun and ocean breeze are waiting for you.Our modern Beach House is located 2 minutes walk from the beautiful and quite beach with direct beach access.Its a newly built three story house with nice and private backyard,heated pool,hot tub and beautiful rooftop.We have everything that you need for bigger groups of families to relax on your Beach vacation.Our Beach House is in a quite neighborhood and walking distance from restaurants,bars and stores. BTR#209

4.98 out of 5 average rating, 103 reviews

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

4.98 out of 5 average rating, 121 reviews

A cozy outdoor space is illuminated by string lights at night. It features a fire pit with glowing embers, a hammock between two posts, and two seating areas on a grassy patch. A storage unit is visible, adding functionality to the setting.

Guesthouse in Clearwater

Cozy 2 Bedroom - 12 Minutes from Clearwater Beach

Make your vacation relaxing, fun and easy! - Kick back in the hammock or have some coffee with loved ones in the peaceful private backyard. - Take the 12 minute drive to the beach with the provided boogie boards, chairs and sand toys. - Take a walk or bike ride on the gorgeous Pinellas Trail. You'll also find some of the best coffee, food and ice cream on the way. -Golf courses close by. This is a separate unit that shares a driveway and parking area with the front house.

4.88 out of 5 average rating, 164 reviews

A sandy beach stretches into the distance, adorned with scattered seashells and driftwood. Gentle waves roll onto the shore, under a cloudy sky. The horizon blends the sea and sky, creating a serene coastal atmosphere.

Condo in Madeira Beach

Awesome Madeira Beach Location Close To It all!!!

JUST ACROSS THE STREET FROM THE BEACH!!! Enjoy a great vacation stay in Madeira Beach! This is a 1 bedroom 1 bath condo, one floor, easily accessible unit. (One Queen Bed in bedroom, One pull out couch, one Queen murphy bed in living room). I have provided Beach Toys, Beach Cart, Coolers, Chairs Close to Beach Acess, Intercoastal Access, and lots of Restaurants and Bars. Johns Pass is less than a mile away. Madeira Beach is South of Clearwater and North of St Pete Beach

Condo in Clearwater Beach

A well-lit living area features large windows allowing natural light to fill the space. A small dining table accompanies four chairs, while a comfortable seating arrangement includes a blue sofa and an accent chair. Artwork adorns the walls, enhancing the inviting atmosphere.

4.83 out of 5 average rating, 119 reviews

Direct Waterfront "The Lily Pad" Walk to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤

4.91 out of 5 average rating, 124 reviews

Colorful kayaks are neatly arranged on the sandy beach near a thatched-roof pavilion. Sun loungers are visible in the distance, and calm water reflects the clear sky. Palm trees provide a touch of greenery, contributing to the serene coastal environment.

Townhouse in Ruskin

Ruskin Retreat

Our townhome is located in the beautiful Carribean style resort of Little Harbor. Resort amenities for you to enjoy are the large swimming pool and hot tub, basketball court, playground, private kayak launch, private beach (beach chairs and umbrella small fee), water toys for rent. Sunset Bar and Grill adjacent to beach and Hooks by pool , all within walking distance. Disney an hour and a half away and Tampa International Airport only 45 mins.

Apartment in St. Pete Beach

A tidy outdoor area features charming green accents with a bright door leading to a unit. String lights create a soft illumination above a pathway lined with white stones and lush greenery, while a small table and chairs invite relaxation in the pleasant Florida climate.

4.8 out of 5 average rating, 312 reviews

Cactus-Themed Retreat,Walk to Beach<1 mile: 4plex

🌵Fiesta Siesta – Where Every Day Feels Like a Party!🌴 Feed me tacos and tell me I’m pretty—because life’s too short for anything less! Welcome to Fiesta Siesta, a fun, vibrant escape just steps from Upham Beach in sunny St. Pete Beach. One of four uniquely themed units in a gated complex, this playful retreat is decked out in a vibey cactus theme that’s all about fiesta and siesta—because, why choose? Book now and let the fiesta begin! 🎉🌮

4.91 out of 5 average rating, 173 reviews

A well-maintained staircase with beige carpeting is pictured, featuring white wooden railings and spindles. The walls are painted in a neutral tone, and a small wall-mounted shelf is visible beside the stairs, enhancing the clean design.

Condo in Redington Beach

2min walk to the beach/pool, BBQ/great area, RO110

Enjoy a great getaway in this well maintained 1 bedroom 2 bath condo in a quiet small complex, only a 2 minute walk to one of the best beaches on the west coast of Florida. This area is amazing and has a ton of things to do and see and great restaurants within walking distance. We have provided the majority of the necessary beach gear, towels,etc... Full kitchen, keurig and coffee maker & heat/pool. Parking is available for 1 car only.

4.96 out of 5 average rating, 139 reviews

A wooden boardwalk leads across sandy terrain towards the beach, bordered by lush greenery and palm trees. The sun is setting on the horizon, casting warm light over the ocean, which reflects the sky's vibrant colors.

Condo in Indian Shores

Good Times and Tan Lines @ #105intercoastal

** Heated Pool ** | Great vacation location | Check the reviews below: 2 Bedroom / 2 Bath Condo across the street from the award-winning beaches of St Pete. All the conveniences you would expect! Granite counter tops, kitchen appliances, dishwasher, washer/dryer, new towels and linens, beach towels, 4K Smart TV, Cable TV, WIFI and AC. Grounds with private pool, small pool side grill, sunbeds, tables & chairs and restroom.

4.98 out of 5 average rating, 240 reviews

A serene beachscape is captured under a clear blue sky, featuring soft white sands that lead to gentle waves. The water transitions from light turquoise to deep blue. A few figures can be seen enjoying the shoreline in the distance, enhancing the peaceful atmosphere.

Apartment in Dunedin

My Favorite Place 🍊downtown & city approved

LEGAL, CITY APPROVED 1 bedroom apartment w full kitchen, living , dining & separate bedroom located on the red brick streets of downtown Dunedin. Private entrance. BIKES Super clean Private driveway free parking Two great bikes Great for couples Tastefully decorated. Comfortable Queen bed. Luxurious bedding. Super clean. Shampoo, conditioner, body wash, coffee, tea, drinking water provided. SUPER CLEAN No pets

Cottage in Indian Rocks Beach

A view of the beach is captured from a balcony, showcasing vibrant turquoise waters and a sandy shore. Sunbathers and colorful umbrellas dot the beach, while charming coastal cottages frame the scene. The image conveys a relaxed atmosphere, with soft ocean waves visible in the background.

5 out of 5 average rating, 45 reviews

Upper Deck prime area no condos/crowds

The location is one of the best on the West Coast. I’ve had only 5 stars from my guests. Our places are fully stocked and very clean. This whole property is award winning! Plus, we attract artists -Also our cottages have appeared on many calendars, cards and artists' canvas.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Wesley Chapel vacation rentals

Stay near Wesley Chapel's top sights

Wiregrass Sports Complex3 locals recommend

The Brass Tap33 locals recommend

Main Event Wesley Chapel17 locals recommend

Florida Hospital Center Ice23 locals recommend

Burger King18 locals recommend

Florida Avenue Brewing Co.8 locals recommend

Pet-friendly vacation rentals in Wesley Chapel

4.72 out of 5 average rating, 217 reviews

A well-appointed room showcases a spacious bed with soft linens against a light-colored wall. Natural light streams through multiple windows, enhancing the comfortable seating area featuring a gray sofa and small white dining table. A touch of greenery is added with a potted plant.

Hotel room in Dunedin

Seaside Artisan *Dog Friendly* 5

Apartment in Madeira Beach

The living area features a daybed with an orange cover, adorned with decorative pillows, including one shaped like a lime. A small table sits in front of the daybed, and a turquoise rug adds a pop of color to the tiled floor. A large window allows natural light to brighten the space.

4.98 out of 5 average rating, 107 reviews

MARGARITAVILLE ACROSS THE STREET FROM BEACH ACCESS

4.91 out of 5 average rating, 257 reviews

A spacious bedroom features a large bed with a textured blanket and decorative pillows. Natural light enters through multiple windows, illuminating the light grey walls and wooden floor. A ceiling fan is seen above, and an entrance to a closet is visible on the left.

Home in Dunedin

Wonderful family friendly home in Dunedin FL

4.96 out of 5 average rating, 205 reviews

A private outdoor patio area is enclosed by a wooden fence, featuring potted plants and colorful landscaping. Two chairs and a small table are positioned for relaxation, with sunlight filtering through trees, creating a serene outdoor space.

Cottage in Dunedin

Adorable Dog-Friendly Cottage in Quaint Dunedin

Bungalow in Indian Shores

A beachfront bungalow is framed by lush greenery and soft sandy surroundings. The charming structure features large windows and a welcoming porch, with a few colorful chairs visible. A friendly dog stands in the foreground, enhancing the inviting atmosphere of the outdoor space.

4.95 out of 5 average rating, 152 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

4.8 out of 5 average rating, 139 reviews

An outdoor patio area features a round table surrounded by four floral-patterned chairs. The seating space is complemented by a wooden deck and colorful wall art is visible on the siding. Lush greenery frames the entrance, creating a serene outdoor environment.

Home in St. Petersburg

Close to all with a King-bed! Bikes included

Home in Old Seminole Heights

4.82 out of 5 average rating, 176 reviews

Reel relaxing on the river walk 2 Lowry Park Zoo

4.89 out of 5 average rating, 111 reviews

A kitchen is seen with wooden cabinets and modern appliances. A black refrigerator and a microwave are positioned alongside a stove. Light-colored walls create a bright space, while a doorway at the back leads to a bathroom. Natural light filters in from nearby windows.

Apartment in Largo

Banana Mania Cottage 3 - few miles to beaches

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Other great vacation rentals in Wesley Chapel

4.97 out of 5 average rating, 32 reviews

The exterior of the home features a spacious driveway leading to a two-story structure with a charming balcony. Lush greenery and manicured landscaping enhance the inviting curb appeal, complemented by soft sunset colors illuminating the sky.

Home in Palma Ceia

SouthTampa-Family&Group Oasis-3K bd, private pool

Cottage in Indian Rocks Beach

The entrance features a bright pink exterior, complemented by white trim and a welcoming white door labeled 'B.' Lush green plants are arranged on either side of the door, enhancing the cheerful appeal. A well-maintained artificial lawn lies in front, with a simple concrete pathway.

4.9 out of 5 average rating, 287 reviews

Vintage Florida Beach Cottage B

Apartment in Indian Rocks Beach

4.8 out of 5 average rating, 274 reviews

Enjoy brand new vacation 2/2 condo & water park!

4.77 out of 5 average rating, 31 reviews

A modern kitchen features white cabinetry with sleek handles and a spacious countertop. Stainless steel appliances, including double ovens and a cooktop, are integrated into the design. Under-cabinet lighting adds a bright ambiance, highlighting the elegant marble backsplash.

Home in Holiday

Luxurious holiday home

4.9 out of 5 average rating, 10 reviews

A spacious living room is displayed, featuring elegant furniture arrangements on glossy tile floors. Natural light brightens the area through large windows. A staircase can be seen in the background, leading to an upper level, while a dining area is visible in the adjacent space.

Home in Tampa

Bring your family and friends to our luxury airbnb

4.9 out of 5 average rating, 106 reviews

Home in Tampa

Luxury Home centrally located in Tampa Bay!

4.78 out of 5 average rating, 281 reviews

The pool area features a curved swimming pool surrounded by vibrant greenery and palm trees. Several lounge chairs are arranged on the side. The area is enclosed by a white fence, providing a sense of privacy.

Apartment in Largo

Mini-Golf 2/1 with Heated pool.