Downtown, Sarasota vacation rentals

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Top-rated vacation rentals in Downtown, Sarasota

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Guest favorite

Home in Bradenton

5 out of 5 average rating, 27 reviews

Sunshine Family Paradise With Heated Pool & King B

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

Superhost

Home in Sarasota

4.78 out of 5 average rating, 54 reviews

Siesta Key Cottages Crescent 1D Beach/Pool/Hot Tub

4 separate BRAND NEW inside (renovated 12/24) 2 bedroom/2 bath (+Queen Sofa Bed+ Chair/Bed) pool homes (Each sleeps 7) with only a 4 minute walk (no major streets to cross) to the #1 Beach in the USA: Siesta Key. First Class! 2 Heated Pools, 2 hot tubs,2 gyms, Smart TV’s in all rooms, fine linens, towels, bikes, beach equipment, private porch, grill, fire pit, outdoor shower, private parking: Great restaurants / nightlife in walking distance. Running/Walking: You have miles of beach to take in!

Guest favorite

Home in Sarasota

4.88 out of 5 average rating, 52 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!

Guest favorite

Home in Sarasota

4.88 out of 5 average rating, 146 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.

Guest favorite

Condo in Sarasota

4.97 out of 5 average rating, 37 reviews

Post storm re-opening January 17, Siesta Key

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.

Guest favorite

Home in Sarasota

5 out of 5 average rating, 13 reviews

Beautiful Home/King Beds

This cheerful home offers two king beds and a set of twin beds with plush bedding. There is a laundry room in the garage for our guest's convenience. Yoder's Fresh Market, Earth Origins, as well as Publix and Walmart Marketplace are nearby to grab groceries and Downtown Sarasota has an amazing assortment of restaurants. Check out our guidebook to view our favorite local spots and activities. This property is approximately - 7.5 miles to Siesta Key Beach - 7 miles to Lido Key Beach

Guest favorite

Home in Sarasota

4.92 out of 5 average rating, 285 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.

Guest favorite

Home in Sarasota

4.86 out of 5 average rating, 7 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.

Superhost

Home in Sarasota

4.75 out of 5 average rating, 4 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.

Guest favorite

Home in Bradenton Beach

4.82 out of 5 average rating, 133 reviews

50 Steps to Beach Villa Hot Tub 1bd modern cottage

Luxury Beach Cottage w/ HOT TUB, Fire Pit & BBQ. 1 bed/2bath sleeps 4 This is your chance to enjoy a unique getaway on the nicest beach! Stay in our newly remodeled beach cottage. White sandy beach & turquoise water is literally 50 ft from the door. Everything you need for a delightful & relaxing day at the beach is included. Chairs, beach towels, umbrella, snorkels, masks & a cooler. Enjoy the convenience of this premium location across Gulf blvd to Beach.

Guest favorite

Home in Sarasota

4.99 out of 5 average rating, 365 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!

Guest favorite

Home in Siesta Key

4.96 out of 5 average rating, 102 reviews

Beachfront home with private access, walk to town!

Welcome to your own private getaway directly on Siesta Beach! Meticulous, updated unit with amazing location to the village and access to tow You will literally, walk out your door, down the steps, and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedroom 3 bathroom beachfront home with Gulf views that sleeps 8.