Villa rentals near Anna Maria Island

4.92 out of 5 average rating, 160 reviews

The exterior of the villa features a light-colored facade with inviting landscaping. Tropical plants and palm trees are positioned around the entrance, which is framed by large windows and a welcoming pathway made of stone pavers leading to the front door.

Villa in Nokomis

NOV SALE! 1 min to beach, New!, PETS OK!, 2Br/2BTH

EXCLUSVE CASEY KEY beach just .5 mi. away!! Sarasota 10 mins away! Miles of uncrowded beach! Two KING bedrooms, two bath villa! The Villa is a short 1 minute drive from Casey Key Beach! Two new 55" 4K T.V's. New appliances and furnishings throughout! Kayaking, biking, boating... all right here! Lush tropical backyard and fire pit. There are many wonderful restaurants and shops within a five minute drive. Restoring this Villa has been a labor of love for us, read our reviews!! Come stay...:)

A light-filled living area features soft, neutral-toned sofas arranged around a glass coffee table atop a textured area rug. Decorative elements, such as a floral arrangement and softly glowing lamps, complement the inviting atmosphere. A doorway leads to the kitchen, enhancing the open layout.

4.86 out of 5 average rating, 123 reviews

Updated Downtown Sarasota Villa, 2b/2b

Enjoy a stylish experience at this centrally-located 2 bedroom, 2 bathroom attached villa in historic Laurel Park, downtown Sarasota. New 75” smart TV! Sleeps 6. Bedroom 1: King bed w/ en suite bathroom. Bedroom 2: 2 queen beds. Granite kitchen. 2 bathrooms. Fenced outdoor paver patio w/washer & dryer. Updated 2022. Free parking outside villa. Walking distance to downtown Sarasota, Selby Gardens, Marina Jack, Main St & more. Pottery Barn furnishing, beachy vibe & free WiFi! Free parking too!

4.94 out of 5 average rating, 127 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!!

4.97 out of 5 average rating, 36 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

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, 218 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, 146 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, 294 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

5 out of 5 average rating, 5 reviews

Villa in Holmes Beach

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.

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, 116 reviews

Tropical Luxury Villa: 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 and blackout shades 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!

4.9 out of 5 average rating, 117 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

4.83 out of 5 average rating, 132 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

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.

A modern kitchen area features sleek white cabinetry, gray countertops, and stainless steel appliances. An island with two black stools offers additional seating. Well-lit by overhead fixtures, the space includes a door leading to an entrance and a doorway to a small adjacent room.

4.88 out of 5 average rating, 172 reviews

Boho -Minimalist villa

Welcome to our Boho Minimalist Villa 4311 unit B with a 2 bedroom and 1 bathroom. Conveniently located in the heart of Tampa, Florida. “Points of interest” to visit and enjoy while you are here: Raymond’s James Stadium, New York Yankees Training Camp, Hillsborough Community College, International Tampa Airport, Downtown Tampa, Midtown within less than 10-minutes’ drive enjoy a great afternoon eating at many local restaurants.

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, 39 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, 83 reviews

Paradise Villa- Sarasota

4.88 out of 5 average rating, 26 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

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.

4.93 out of 5 average rating, 15 reviews

Remodeled Mid-century POOL house

4.76 out of 5 average rating, 109 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

My Little House - 2/2 on a lake

5 out of 5 average rating, 40 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

4.93 out of 5 average rating, 73 reviews

Villa in Siesta Key

Siesta Key*PRIVATE BEACH*Gulf Side*Heated Pool

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, 249 reviews

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

Luxury villa rentals

4.98 out of 5 average rating, 47 reviews

Luxury 4-Bedroom Pool Retreat Near Siesta Key

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, 79 reviews

Luxury home in the heart of South Tampa & POOL!

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.

4.92 out of 5 average rating, 138 reviews

1 House to beach! Peaceful beachside getaway

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, Grill, WiFi

A tranquil pool area is highlighted by a sparkling blue water surface, surrounded by lush greenery. Comfortable lounge chairs are arranged nearby, adorned with striped pillows. A gentle waterfall feature adds a serene touch, while a privacy fence encloses the space.

5 out of 5 average rating, 29 reviews

(BAYC) Heated Pool Villa. Boat rental available

4.98 out of 5 average rating, 41 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

4 min Walk to Beach, Pool, Roof Deck

4.95 out of 5 average rating, 66 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

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.

4.94 out of 5 average rating, 47 reviews

Coastal Villa w/ Amazing Courtyard - Splash Pad!

Villa rentals with a pool

The image portrays the exterior of a villa nestled among lush greenery. A palm tree and flowering plants are visible in the foreground, while a driveway leads to a garage with a side entrance. A warm, terracotta roof complements the beige walls of the home.

4.8 out of 5 average rating, 35 reviews

Private Tropical Paradise

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.

4.89 out of 5 average rating, 201 reviews

Villa Perdomo Family

A villa with a light-colored exterior features a spacious driveway made of pavers. Lush tropical landscaping adds color, while a large parking garage is visible on the right side. In the background, a multi-story building is partly shown under a partly cloudy sky.

5 out of 5 average rating, 9 reviews

Newly Remodeled Luxury Beach Villa on Siesta Key!

4.67 out of 5 average rating, 9 reviews

Villa Siesta II -Downtown Secret Community & Pool!

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, 125 reviews

Busch Gardens Deluxe Edition w/heatedpool

A modern kitchen features sleek cabinetry, stainless steel appliances, and a central island with seating. Light-colored countertops and wood grain flooring create a bright and inviting space. Natural light is provided by a window, while an open layout connects the kitchen to the living area.

4.84 out of 5 average rating, 55 reviews

Your own tropical paradise in Sarasota

A spacious lawn surrounds the villa, featuring tropical landscaping and a patio area with seating. A pool is visible alongside the well-maintained pathway, leading to the water. The structure showcases large windows that invite natural light, presenting a warm outdoor setting.

4.89 out of 5 average rating, 85 reviews

The Palm Island Villa Luxury 4 BDR Waterfront Home

A welcoming entrance is framed by lush greenery, featuring a gravel driveway leading to a modern one-story house. Large wooden doors provide access, while well-maintained landscaping adds to the inviting atmosphere.

4.95 out of 5 average rating, 61 reviews

Beautiful House w/ Pool, 10 Min to Siesta Beach

Villa rentals with a hot tub

5 out of 5 average rating, 32 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

4.8 out of 5 average rating, 49 reviews

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.

Villa in Clearwater

La Villa, 1 of 3 rentals on-site, pool, near beach

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

The exterior of a single-story villa is shown, featuring a terracotta roof and landscaped grounds. Lush green grass surrounds the home, which is complemented by colorful shrubs and trees, offering a peaceful and inviting appearance.

4.95 out of 5 average rating, 19 reviews

7845 Timberwood Cir, Sarasota, FL 34238

5 out of 5 average rating, 11 reviews

A clear swimming pool rests within a screened enclosure, surrounded by tropical greenery. Comfortable lounge chairs are positioned by the water's edge, inviting relaxation. The pool features a connected hot tub, offering options for leisure and enjoyment.

Villa in Wimauma

Coastal Farmhouse & Pool

4.96 out of 5 average rating, 48 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.

4.84 out of 5 average rating, 50 reviews

Relaxation awaits in this bohemian inspired villa