Villa rentals near Anna Maria Island

4.95 out of 5 average rating, 146 reviews

An outdoor patio area features a dining table adjacent to a heated pool. Lounge chairs are positioned nearby, under a screen enclosure. The pool is framed by a laid stone surface, with a view of lush greenery beyond the surrounding fence.

Villa in St. Petersburg

Heated Pool! Huge Walk In Shower! 5 min to beach!

Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

5 out of 5 average rating, 27 reviews

A private patio area is displayed with a round table surrounded by six chairs and a large umbrella. Two lounge chairs are positioned nearby. The exterior features large windows reflecting a vibrant sunset, enhancing the tranquil atmosphere.

Villa in Holmes Beach

Seaside Inn a waterfront in Paradise

Welcome to Seaside Inn, a CLEAN, single story, waterfront, 2/2 + bath en-suite that sleeps 6. Enjoy the island breeze on the private patio watching the sunrise or the dolphins swim by, spend time in the open concept, fully equipped kitchen, the perfect place for gathering with family and friends over a meal . We have patio seating, a fire pit area with cafe lighting, laundry, shared dock with water & electricity & so much more! Please save our listing to find us quickly! License # DWE5106414

4.96 out of 5 average rating, 49 reviews

A cozy bedroom features a spacious bed with light bedding, accented by decorative pillows. Natural light streams through sheer curtains by the window, illuminating the room's soft blue walls. A wooden dresser and a ceiling fan add functional elements to the friendly space.

Villa in Holmes Beach

Starfish House - 2bed/2bad

An Anna Maria Island Vacation to remember is waiting for you at Starfish Beach #4. This charming complex is small and quiet, perfect for a relaxing beach getaway. A shared pool is available in the courtyard. You'll enjoy being just steps from the Anna Maria Public beach access. With a short walk, finding your place in the sand each morning will be easier than ever! 50 yards to the BEACH! Bed size: 1 K, 1 Q, sleeper Baby accessories available for rent. Snoo Bassinet high chair pack and play

5 out of 5 average rating, 153 reviews

A spacious living room features a large sectional sofa adorned with green pillows and a coffee table placed on a vibrant area rug with palm leaf designs. A flat-screen TV is mounted on the wall, complemented by decorative accents and artwork throughout.

Villa in Safety Harbor

Villa Key West "Villas by Christine"

Perfect location, Charming Villa Guests are loving the newly renovated Villa Key West. Christine's goal was to make guests to feel the charm of a Key West Villa while experiencing the amenities of a 5 star hotel The Living room and bedrooms have large smart TV’s with complementary Roku, Netflix, Prime and Hulu. Enjoy the view out back of one of Safety Harbors 150 year old Oak & nature pond. We are per friendly. Please let us know you will be bringing pet. Pet fee of $100.00 due upon arrival.

A spacious living area is highlighted by a large sectional sofa and a wooden coffee table. A TV sits atop a media console, while glass doors provide access to the outdoor patio, allowing natural light to fill the room.

4.9 out of 5 average rating, 232 reviews

Entire Standalone Villa,1.2k sf,1 block Lido Beach

Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!

4.89 out of 5 average rating, 28 reviews

A charming beach home is set among palm trees, with a landscaped garden featuring colorful plants. A gravel pathway leads to the entrance, and patio seating is visible in the background, inviting guests to enjoy the outdoor space.

Villa in Anna Maria

Northshore BeachHouse West Anna Maria Island

Nine houses away from the white sandy beaches, Pine Ave and Northshore Drive is an adorable beach home located on Anna Maria Island. It is the perfect vacation beach house located at the north end of the historic village of Anna Maria Island. Just steps away from Pine Ave, the beach, restaurants, and shopping, guests can walk conveniently everywhere. Jeff and I have lived and worked here on Anna Maria Island for over 20 years, and would love to share our little piece of paradise with you!

The exterior of the home is surrounded by lush tropical foliage, including palm trees and native plants. A covered patio area can be seen, leading to a pathway of gravel that weaves through the vibrant garden. The inviting entrance is framed by greenery, creating a serene atmosphere.

4.98 out of 5 average rating, 165 reviews

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.

4.98 out of 5 average rating, 129 reviews

Luxury Villa with Pool, Game Room, Near Beach

Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. • Bedrooms: 4 private suites, plush linens to ensure restful nights. • Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. • Heated pool & sun loungers • Arcade-style game room • Fast Wi-Fi & 5-star cleanliness • Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today! VR24-00060

4.91 out of 5 average rating, 130 reviews

The Tropical Oasis, w/ Solar Heated Pool and Games

Welcome to your private, tropical escape! Unwind by the solar-heated pool in a screened, mosquito-free lanai. FUN & GAMES: Enjoy Billiards (Pool Table) 🎱, Foosball, Cornhole, board games, and 3 Smart TVs 📺. PRIME LOCATION: Only 5 min 🚗 to Indian Rocks & Bellaire Beach, FL Botanical Garden, and dining. Essentials: 🌞 Heated Swimming Pool (Private!) 🎮 Billiard Table / Foosball Table / Cornhole / Boardgames and more! 🛏️ 4 Queen/Full Beds 🧺 Beach Amenities

4.83 out of 5 average rating, 150 reviews

An outdoor space features a sparkling swimming pool surrounded by a screened enclosure. A hot tub is adjacent to the pool under warm string lights. Various games are available, including a ping pong table and a billiard table, providing entertainment options for guests.

Villa in Brandon

Resort pool/ home hot tub game room near airport

Welcome to home away from home! This beautiful 4 bedroom 2 bathroom house is new with modern decor and has everything you need for a comfortable and relaxing stay. The house features a sparkling swimming pool and a hot spa, perfect for unwinding after a long day. Located in brandon, you’ll be just 15 minutes away from downtown, where you can experience the city’s vibrant culture and attractions. Get ready to create some unforgettable memories in this charming abode.

Villa in Redington Shores

4.88 out of 5 average rating, 146 reviews

Beach so close! 1 house to beach Peaceful area

1 HOUSE TO BEACH! A 30 second walk. 1 of 3 units in a private beachside villa tucked away on a peaceful street. A hidden gem away from busy condos. Wide beautiful beach goes for miles. Walk to many restaurants. **Washer/dryer in unit. *Private patio. *Full sized kitchen. *Quiet ductless AC, *Free parking in front. *BEACH supplies provided. 1 bedroom super comfy queen bed, separate living room very comfortable pop-up sofa. 2 more units available; 1 bdm & 3 bdm.

A charming gazebo is positioned beside a serene pool, surrounded by vibrant greenery. The calm waters of Lake Seminole reflect the pastel colors of the sunset sky, while the gazebo offers shaded seating for relaxation.

4.91 out of 5 average rating, 121 reviews

Waterfront Heated Pool, Sleeps 20 - 4plex

Welcome to 101st Largo 257 by EscapeStays, the name guests can easily remember when planning their stay. Welcome to LAKESIDE RETREAT 4-plex, situated on a ⅓ acre next to Lake Seminole. Enjoy the perks of a private resort with amenities like a lakefront pool, a gazebo, and a cozy fire pit. The property is a 15-min drive to popular beaches, John’s Pass, and the Lake Seminole Park boat ramp. ✨ "Perfect place! Exceeded our expectations! thank you so much!" ✨

Popular amenities for villa rentals near Anna Maria Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

Villa in Indian Rocks Beach

An aerial view showcases a coastal neighborhood along the intracoastal waterway, featuring a single-story home with a gray roof and a landscaped front yard. Palm trees line the driveway, and nearby properties reflect a variety of architectural styles, emphasizing the serene waterfront setting.

5 out of 5 average rating, 45 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

5 out of 5 average rating, 27 reviews

Villa in Bradenton

Lilo & Stitch Ohana Villa|Heated Pool Near AMI

4.92 out of 5 average rating, 12 reviews

Two light blue adirondack chairs and a small table are positioned by a dock along the intercoastal waterway. The clear sky and calm water reflect greenery and colorful coastal homes in the background, creating a relaxing outdoor setting.

Villa in Longboat Key

Waterfront Condo, Close to Beach, with Boat Dock!

5 out of 5 average rating, 8 reviews

Villa in Belleair Beach

Gorgeous Villa with Heated Pool & Beach Views!

4.67 out of 5 average rating, 3 reviews

Villa in Bradenton

Villa Summerwind 3bed/2bath pool villa

4.71 out of 5 average rating, 17 reviews

Villa in Holmes Beach

the Seaside 21

An outdoor area features a lighted splashpad at the center, surrounded by pavers and tropical landscaping. Lounge chairs are positioned nearby, offering a relaxing spot to enjoy the serene atmosphere as soft lights illuminate the garden under a sunset sky.

4.89 out of 5 average rating, 65 reviews

Coastal Villa w/ Amazing Courtyard - Splash Pad!

4.93 out of 5 average rating, 74 reviews

Villa in Siesta Key

Siesta Key*PRIVATE BEACH*Gulf Side*Heated Pool

Luxury villa rentals

4.97 out of 5 average rating, 37 reviews

A spacious heated saltwater pool is surrounded by a screened enclosure, featuring colorful inflatable floats. A playroom is visible with cheerful decor, while a cozy media room offers comfortable seating. The exterior showcases a welcoming home, with a yard perfect for children’s play.

Villa in Dunedin

Family Haven/Kid's Amenities Near Honeymoon Island

An outdoor space features a heated pool surrounded by lounge chairs in a vibrant yellow hue. A fire pit is situated at the center of the patio, while the villa's upper balcony overlooks the serene setting, framed by lush greenery and a blue sky.

4.9 out of 5 average rating, 68 reviews

Clearwater Villa Heated Pool, Golf, 4K Projector

4.97 out of 5 average rating, 62 reviews

Luxury 4-Bedroom Pool Retreat Near Siesta Key

The exterior of The Belleair Estate is showcased from an aerial view, featuring lush landscaping surrounding the home. A private pool glistens alongside the water, with the expansive lawn leading to a private boat dock, creating a serene waterfront setting.

4.77 out of 5 average rating, 31 reviews

The Belleair Estate | Waterfront & Heated Pool

An open dining area features a wooden table set for six, with white plates and dark napkins. A stylish light fixture hangs above, illuminating the space. The adjoining kitchen area includes dark cabinetry and modern appliances, offering a seamless flow between dining and cooking.

4.86 out of 5 average rating, 64 reviews

Best deal in town!

A rooftop terrace is shown with two lounge chairs and a small table. A large umbrella provides shade, while a view of the waterfront and city skyline is visible in the background. The sky displays soft hues of purple and pink, enhancing the serene setting.

4.98 out of 5 average rating, 49 reviews

Walk to Beach (4 min), Pool, Private Roof Deck

Villa in Indian Rocks Beach

4.92 out of 5 average rating, 96 reviews

The Emerald Villa, Eco-Luxury by the Sea

A spacious living area features a light gray sectional sofa paired with a round wooden coffee table. The room is illuminated by natural light streaming in through multiple windows. An inviting ceiling fan circulates air, while a large television is mounted on the wall, enhancing the entertaining space.

5 out of 5 average rating, 60 reviews

Tampa Downtown Luxury Villa | Beds 14 Park 6 cars

Villa rentals with a pool

The exterior of a single-story home is showcased, featuring a covered entryway with double doors. Lush greenery, including potted palm trees and trimmed shrubs, frames the entrance. A concrete path leads through a pebble-strewn area, offering a welcoming appearance on a sunny day.

4.83 out of 5 average rating, 93 reviews

Paradise Villa- Sarasota

5 out of 5 average rating, 22 reviews

An outdoor pool is featured, surrounded by a spacious deck with lounge chairs. A hot tub is adjacent to the pool, and a waterfront view includes a wooden pier extending into the water, framed by lush greenery and a clear blue sky.

Villa in Palmetto

The Sea House

A swimming pool is set against a backdrop of lush greenery and palm trees. A safety fence surrounds the pool area, and a blue shade sail provides protection from the sun. Poolside seating is available, along with a floating pool item resting on the water.

4.87 out of 5 average rating, 221 reviews

Villa Perdomo Family

A serene outdoor pool area is enclosed by a screened structure, allowing for a private retreat. Sun loungers are positioned beside the clear, inviting water, and lush greenery surrounds the pool, enhancing the tranquil setting.

4.97 out of 5 average rating, 90 reviews

Luxury home in the heart of South Tampa & POOL!

5 out of 5 average rating, 51 reviews

Siesta Villa

The image features a serene private pool surrounded by a stone patio. A screened-in lanai is visible in the background, with seating arrangements that offer a relaxing view of the pool. The villa's vibrant exterior adds a welcoming touch to the outdoor space.

4.89 out of 5 average rating, 198 reviews

Hansen- Gorgeous 3BR/2BA Villa near Siesta Key

4.92 out of 5 average rating, 77 reviews

A heated pool is surrounded by comfortable loungers and shaded by a stylish cabana. A spacious patio area features outdoor seating, while lush greenery and tall trees create a serene backdrop under the clear blue sky.

Villa in Seminole

5 BR Luxury Beach Villa: Heated Pool & Games Room

A saltwater pool is featured with a large yellow inflatable duck wearing sunglasses. Water splashes create a lively ambiance, while a shaded patio area is visible in the background. Roller coasters can be seen beyond the pool area, highlighting the proximity to attractions.

4.91 out of 5 average rating, 141 reviews

Busch Gardens Deluxe Edition w/heatedpool

Villa rentals with a hot tub

4.96 out of 5 average rating, 52 reviews

An outdoor patio area features a private pool surrounded by a spacious deck. A seating arrangement with chairs and a table is positioned nearby, along with a sauna. The setting is complemented by lush green grass and a colorful sunset sky.

Villa in Seminole

[TRENDlNG] Modern 5BR Pool Villa + Arcade & Sauna

4.75 out of 5 average rating, 8 reviews

An outdoor area features a spacious patio with a large dining table and several chairs, set among lush tropical greenery. A pool is visible nearby, surrounded by lounge chairs. A spiral staircase leads to an upper level, adding architectural interest to the space.

Villa in Anna Maria

Bean Point Residence Unit B by SeaBreeze Vacation

A spacious pool area is highlighted, showcasing a turquoise pool surrounded by potted plants and tropical foliage. The villa's exterior features large windows that emit a warm glow, creating an inviting ambiance as dusk sets in.

4.78 out of 5 average rating, 58 reviews

La Villa, 1 of 4 rentals on-site. Heated Pool!

4.9 out of 5 average rating, 20 reviews

Villa in Wimauma

Country Coastal Farmhouse

4.94 out of 5 average rating, 53 reviews

An outdoor space features a circular fire pit surrounded by several black Adirondack chairs, all set on gravel. The background showcases a heated pool and spa, with a vibrant sunset sky illuminating the scene. The villa and dining area are visible, enhancing the inviting atmosphere.

Villa in Seminole

Modern Luxury Villa - Heated Pool Spa, Game Room

An outdoor dining area features a large rectangular table with seating for eight, complemented by a shaded lounge space. A heated pool is visible, along with a sunken hot tub and sun loungers. Lush greenery surrounds the area, providing a serene backdrop.

4.87 out of 5 average rating, 60 reviews

Bohemian Inspired Villa with Golf Cart and SUV

A modern living area is visible, featuring a spacious sofa paired with a low coffee table. Large glass doors open to the waterfront view, allowing natural light to fill the space. A dining area with a marble table and elegant chairs is positioned nearby, accentuated by a stylish chandelier.

4.94 out of 5 average rating, 63 reviews

Waterfront Condo w/ Kayaks, Resort Pool, Sarasota

A charming villa exterior is depicted, featuring a bright façade with a red-tiled roof. Lush green landscaping surrounds the property, with palm trees and various shrubs casting soft shadows on the well-maintained grass.