Vacation rentals in Siesta Beach

4.98 out of 5 average rating, 56 reviews

The outdoor space features a heated pool surrounded by colorful lounge chairs and inflatable pool toys. A shaded seating area is visible, along with a vibrant children's playset in the background. The sky displays a striking sunset, enhancing the relaxing atmosphere.

Home in Bradenton

Sunshine Family Paradise With Heated Pool, Hot Tub

Welcome to your perfect getaway! Located in the heart of the city, our family-friendly retreat offers a perfect blend of comfort and adventure. Dive into a world of nearby activities and attractions, all within easy reach. Enjoy quality time together in our spacious living area or whip up a feast in the fully equipped kitchen. With parks and entertainment just around the corner, every day is an opportunity for fun and laughter. Come and make unforgettable memories in your new home away from home

A clean, large pool is surrounded by comfortable lounge chairs. Illuminated in soft purple light, the pool features colorful inflatables, with a gazebo and grill visible in the background. Palm trees frame the serene lakeside view beyond the pool area.

4.89 out of 5 average rating, 56 reviews

Lakefront Getaway in Sunny FL

Welcome to your lakeside retreat in sunny Florida! Our house offers stunning lake views and spacious, immaculate rooms. Just a short drive to Siesta Beach (#1 in the USA). The main house has 3 beautifully furnished bedrooms. The 4th bedroom in the separate guest house is included for groups of 10 guests; for smaller groups, it can be available for an extra fee. Relax by the large, clean pool in our private, gated property. Well-equipped kitchen, gazebo, grill, and family-friendly features await!

Superhost

Apartment in Bradenton

5 out of 5 average rating, 3 reviews

Five Beach Retreat * Best Value @ Shorewalk Resort

Best Value in Shorewalk Resort * Near beaches of Anna Maria Island & IMG Academy Updated. Soothing sandy neutrals and crisp sea blues. Two bedrooms with full baths. Four beds. Two large sofas provide additional sleeping options. Fully stocked with beach gear. Access to the community's resort-style amenities, including 2 relaxing hot tubs, 2 heated pools, lighted tennis and pickleball courts, outdoor BBQ grills, basketball, shuffleboard & bocce ball courts, a billiard room, and a clubhouse.

Superhost

A bright studio apartment features a spacious bed dressed in light grey linens. Two bedside lamps provide soft illumination. A small kitchenette is visible, while a doorway leads to a bathroom with modern fixtures. Natural light enters through a door leading to the private patio.

Apartment in Siesta Key

4.77 out of 5 average rating, 104 reviews

Gertrude's Siesta | Patio & 1-min to Beach/Village

The Village Studio Top location on island! Apartment with full kitchen, private patio, gated courtyard, in world famous Siesta Village! Leave the car behind and walk to white-sand beaches, 20 bars and restaurants, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Experience a combination of fun ease and relaxation you can't get in other vacations! Book a special getaway now! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta

4.88 out of 5 average rating, 153 reviews

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

4.85 out of 5 average rating, 13 reviews

A spacious living area is illuminated by natural light, featuring a modern layout with an open kitchen and dining space. A large flat-screen TV is mounted on the wall, while seating positions at the island create an inviting atmosphere. Decorative plants add a touch of greenery.

Home in Venice

Sunset Breeze Retreat

Welcome to your serene getaway in South Venice, FL! This cozy and spacious home is your perfect retreat, just minutes from breathtaking beaches and charming local shops and restaurants. Inside, unwind in comfort and style, with plenty of room to relax and enjoy quality time with loved ones. Embrace fun-filled evenings with a foosball table or savor the outdoors with a grill and beach supplies at your fingertips. Your dream vacation awaits in this inviting haven of relaxation and adventure.

4.97 out of 5 average rating, 37 reviews

Condo in Sarasota

Siesta Key Village & Beach w pool & pet friendly

Location and value. No fighting traffic for hours to get to Siesta Key. Park the car and relax. The heart of Siesta Key village waits just outside the back door, and everything is within walking distance at this centrally located condo with a heated pool. The #1 voted beach in the USA and its powder soft sugar sand is an 7-minute walk. Paradise and serenity have been found. One of the few places that will allow your small dog to stay. Also one of the few you can rent for less than a week.

4.92 out of 5 average rating, 294 reviews

❤ Villa & Garden in Downtown ~ 5 Min to Beaches

Our bright and contemporary Heart Villa offers the quintessential Sarasota downtown and beach experience. It is nestled among tropical trees in a charming cul-de-sac in historic Laurel Park – right in the heart of downtown with loads of restaurants, boutiques, and sights on offer. Several fantastic beaches are just 5-mins ride away! And the villa's private garden is the perfect place to enjoy alfresco dining! We’ve poured our hearts & souls into this villa, it's our family business.

4.91 out of 5 average rating, 11 reviews

Slowtide Cottage on Siesta Key

A high-end luxury cottage retreat on Siesta Key. No parties here -- the space was designed and outfitted for those who want a quiet place to relax. 2 bed 2 bath Cottage situated on the Intracoastal water of Siesta Key adjacent to the community pool, tiki bar, fishing dock, fishing pier and deeded private beach access. Meticulously remodeled former ww2 USAAF Barracks from the old SRQ Air Force Base. All new electrical, plumbing, lighting (Buster & Punch), Arhaus furniture.

An outdoor space features a modern tabletop air hockey game and a classic skee-ball machine, inviting friendly competition. The area is surrounded by a lush green garden, with wooden fencing providing privacy, while natural light streams in through screened windows.

4.95 out of 5 average rating, 19 reviews

Warm, Luxury Oasis in Central Sarasota

Choose to stay at a home which has it all. Professionally designed and hosted by a 10-year SuperHost, this property offers incredible value. Superbly comfortable beds and linens, SUPER FAST internet, thoughtful furnishings, tons of activities & games, fully equipped for babies and toddler needs, extremely central location, large, high-end TVs, a jacuzzi, 2-person hammock, in-ground fire pit…. And fur babies welcome… you name it, this home has it. Welcome to Sarasota Paradise.

A spacious living area features a light gray sofa arranged around a dark coffee table, with a neutral area rug underneath. A flat-screen television is mounted on the wall, and large windows allow natural light to illuminate the space, creating a welcoming environment.

4.98 out of 5 average rating, 388 reviews

The Cottage at Central Park II

If you are looking for the perfect family home to cater to your every need, then look no further! With plenty of space to spread out, natural light that pours into every room, an expansive and private fenced in yard, screened-in porch and outfitted kitchen- this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!