Villa rentals near Anna Maria Island

Villa in Redington Shores

A sandy pathway leads through palm trees and lush greenery toward a wide beach. The ocean's calm surface reflects a bright blue sky with scattered clouds. A beach umbrella is visible to the left, suggesting a serene, inviting atmosphere.

4.91 out of 5 average rating, 142 reviews

1 House to beach. Superhost. 2 king beds 2 twin

Steps from a Pristine Beach 🌊 Just one house away from a wide, serene beach perfect for walking. This 1 of 3 units in a small villa is on the beach side, tucked on a quiet street, a hidden gem away from busy condos. Bedrooms & Comfort 🛏️ No one sleeps on a sofa bed! 2 King bedrooms + 1 bedroom with 2 Twin beds (includes W/D). Blackout curtains & comfy mattresses for restful nights. Amenities 🏖️ Beach towels, chairs & cooler. Walk to restaurants. W/D in unit, central AC, Wi-Fi, free parking

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.

4.97 out of 5 average rating, 39 reviews

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

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, 224 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!

4.97 out of 5 average rating, 152 reviews

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.

Villa in Largo

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 single-story home is surrounded by greenery and palm trees, showcasing a light green exterior. A narrow pathway leads to the entrance, flanked by decorative planters. The white fence adds charm and defines the front yard, with large windows allowing natural light into the interiors.

4.88 out of 5 average rating, 295 reviews

Duplex - just mins to Siesta Beach - Pet Friendly

This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

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.

5 out of 5 average rating, 120 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

A serene pool area features a flowing waterfall cascading over textured rocks. The pool water glistens in varying shades of blue, surrounded by palm trees and a spacious patio. Two black lounge chairs are positioned along the poolside for relaxation.

4.91 out of 5 average rating, 101 reviews

Mod Home Heated Pool Resort Backyard 4min to beach

A newly updated modern beach house with a resort style backyard including a HEATED pool, fire pit, outdoor TV with comfortable sectional and an eating area, grill, lounge chairs, corn hole, pool volleyball and much more! All this and it is located just 4 minutes to Indian Shores Beach, and 20 minutes north along the beach is the world famous Clearwater Beach. This house is centrally located with John's Pass only 12 mins away. Downtown Gulfport and St Pete Beach are all 25 mins away.

5 out of 5 average rating, 21 reviews

NEW!~ Beach Front/Heated Pool! Coconuts 107

Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!Relax with the whole family at this peaceful place to stay.

4.9 out of 5 average rating, 122 reviews

Villa in Largo

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

4.8 out of 5 average rating, 5 reviews

the Seaside 21

The Seaside 21 is a stylish waterfront villa in the heart of Holmes Beach on Anna Maria Island. Enjoy coffee on your private dock overlooking the bayou. Just 4 blocks to the beach, with shops and dining nearby. Bring your boat or have a captain pick you up for a day on the water. This weekly rental has been fully renovated and is centrally located. This island oasis is perfect for relaxing, fishing, exploring, and soaking in everything the island has to offer.

4.75 out of 5 average rating, 16 reviews

Anna Maria Island Beach Getaway – Sleeps 6

Just a 8-minute walk from the sugar-white sands of Anna Maria Island and nearby shops and dining, this stylish home offers a resort-style stay with pickleball, tennis, and basketball courts, a park, and a boat ramp—all steps away. This 2-bedroom, 2-bath home, plus an air-conditioned Florida room, sleeps 6 with two queen beds and two twins that convert to a king. Relax in the private backyard or cook in the full kitchen for the ultimate island getaway.

4.76 out of 5 average rating, 176 reviews

A spacious saltwater pool stretches across the backyard, bordered by a paved area featuring lounge chairs. Lush greenery, including palm trees and a nearby canal, enhances the serene outdoor setting under a clear blue sky.

Villa in St. Petersburg

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

Popular amenities for villa rentals near Anna Maria Island

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Private villa rentals

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, 40 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

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.

4.86 out of 5 average rating, 84 reviews

Paradise Villa- Sarasota

4.89 out of 5 average rating, 27 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

4.98 out of 5 average rating, 50 reviews

Luxury 4-Bedroom Pool Retreat Near Siesta Key

An open living area features a gray sectional sofa paired with colorful throw pillows, a white circular coffee table, and a brown armchair. Large sliding doors provide views of the pool area, while natural light brightens the space through sheer white curtains.

4.88 out of 5 average rating, 17 reviews

Remodeled Mid-century POOL house

4.77 out of 5 average rating, 117 reviews

A serene outdoor space is showcased, featuring lush green palm and banana trees gently swaying near a calm body of water. Sunlight reflects off the water's surface, surrounded by a natural landscape of tall grasses and distant trees under a clear blue sky.

Villa in Bradenton

Lakefront 2BR • Perfect for IMG & Long Stays

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.

4.9 out of 5 average rating, 52 reviews

Coastal Villa w/ Amazing Courtyard - Splash Pad!

5 out of 5 average rating, 42 reviews

An enclosed lanai features a heated pool with a curved shape, surrounded by a concrete deck. Colorful lounge chairs in green and red provide seating options. Lush greenery is visible outside the screened area, contributing to a serene outdoor environment.

Villa in Bradenton

River Pointe 3/2 Lakefront Home with Heated Pool

Luxury villa rentals

4.96 out of 5 average rating, 26 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

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.

5 out of 5 average rating, 80 reviews

Luxury home in the heart of South Tampa & POOL!

4.98 out of 5 average rating, 43 reviews

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.

Villa in Clearwater

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

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.

4.91 out of 5 average rating, 69 reviews

5 BR Luxury Beach Villa: Heated Pool & Games Room

4.96 out of 5 average rating, 105 reviews

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.

Villa in Largo

Waterfront Heated Pool, Sleeps 20 - 4plex

4.93 out of 5 average rating, 85 reviews

The Emerald Villa, Eco-Luxury by the Sea

A serene outdoor area features a clear blue pool surrounded by palm trees and inviting lounge chairs. Colorful umbrellas provide shade, while patio seating offers a view of the water. Decorative string lights add a touch of charm to the tranquil setting.

4.95 out of 5 average rating, 60 reviews

Ocean View | Heated Pool | 3 Bed | Island Paradise

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, 41 reviews

Tampa Downtown Lux Villa | Sleeps 14 Park 6 cars

Villa rentals with a pool

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.

4.88 out of 5 average rating, 208 reviews

Villa Perdomo Family

4.68 out of 5 average rating, 65 reviews

A large heated swimming pool is surrounded by lounge chairs and tiki huts, set against the backdrop of a sandy beach and the shimmering Gulf waters. Sunlight reflects off the water, creating a tranquil atmosphere for relaxation and leisure.

Villa in Indian Shores

Relax just steps from beach & Gulf of America

4.67 out of 5 average rating, 9 reviews

Villa Siesta II -Dwntn Secret & pool near beaches!

A private pool area is surrounded by tropical greenery, featuring a wooden deck with smooth steps leading down to the water. Bright lounge chairs sit nearby, and pool floats are casually draped over the railing, inviting relaxation and enjoyment.

4.76 out of 5 average rating, 117 reviews

5 min to Siesta Key, Heated Pool, BBQ, Fast WiFi

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, 128 reviews

Busch Gardens Deluxe Edition w/heatedpool

4.89 out of 5 average rating, 19 reviews

A modern kitchen features wooden cabinetry and a granite countertop, complemented by stainless steel appliances. Red chairs are placed around a dining area visible in the background, with decorative wall art enhancing the space. Natural light filters through the windows, providing a bright atmosphere.

Villa in Treasure Island

Luxury waterfront in the heart of treasure island

A comfortable living area features a gray, U-shaped sectional sofa accompanied by a center coffee table. Natural light brightens the space, highlighting the light-colored tile flooring. The open layout connects the living area to a kitchen visible in the background.

4.92 out of 5 average rating, 39 reviews

Fully renovated villa on Siesta Key

The living area features a green sofa adorned with decorative pillows, paired with a round coffee table on a jute rug. A warm brick fireplace complements the space, which opens up to the pool area through large windows framed by sheer curtains.

4.74 out of 5 average rating, 262 reviews

Perfect Location w/ pool -close to beach or DT!

Villa rentals with a hot tub

4.83 out of 5 average rating, 139 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

Tampa heat pool /hot tub lake view near airport

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.

5 out of 5 average rating, 39 reviews

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

4.71 out of 5 average rating, 7 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

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

4.91 out of 5 average rating, 32 reviews

A private patio area features a hot tub surrounded by wooden decking. Soft lighting from string lights enhances the ambiance. A cozy fire pit sits beside comfortable seating, ideal for relaxation. Nearby, a hammock is available for lounging, adding to the outdoor comfort.

Villa in St. Petersburg

King 1 Br/1Ba, Hot Tub - Close to Beach & Downtown

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.

4.94 out of 5 average rating, 49 reviews

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.

4.85 out of 5 average rating, 52 reviews

Relaxation awaits in this bohemian inspired villa

A wide view of the intercoastal waterway reveals vibrant turquoise waters and a private dock. Lush greenery and a spacious pool area are visible, featuring a unique shape and several lounge chairs. The serene setting offers an inviting outdoor space for relaxation.