Holiday rentals in Downtown, Sarasota

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Top-rated holiday rentals in Downtown, Sarasota

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Rental unit

4.97 out of 5 average rating, 215 reviews

Modern Private Apartment 1 Block from Sarasota Bay

One block from Sarasota Bay - completely remodeled and fully furnished guest apartment with a Miami deco feel. The unit is a little over 300 sf with full kitchen, one bathroom w/ shower, comfy queen bed, several stools/ chairs, flat screen tv, wifi, off-street parking, six USB ports for easy charging and sitting area outdoors on front porch. Five minutes to downtown or SRQ airport, 15 minutes to Lido Beach, and 25 minutes to Siesta Beach with easy access to University Parkway or Fruitville Rd.

Guest favourite

Rental unit

4.99 out of 5 average rating, 111 reviews

*Recently Updated* Cozy Oasis, centrally located

This cozy yet spacious apartment is very centrally located... Just 5 min from downtown, 10-15 min from Siesta and Lido bch and St Armands Crl, and within walking distance of the historic Amish district. The newly completed Legacy Trail (perfect for walking, biking...) is less than a 5-minute walk away. The space is very private and clean and Ive taken extra measures to ensure your absolute peace and comfort. It includes all the amenities you'll need to make your getaway a memorable one.

Guest favourite

Home

4.98 out of 5 average rating, 120 reviews

The Sweet Spot! Walk to DT and Bayfront Sunsets!

Looking for the Sweet Spot in Sarasota? Look no further! This artistically updated cottage, nestled in the quiet, historic downtown neighborhood of Laurel Park is within a safe walking distance to some of the best downtown dining, shopping and arts venues. The beaches, Ringling Museum and many other SRQ attractions are just a short drive away. It's the perfect place for a couple's getaway, a "family of four" vacation, a weekend away with friends, or a long term stay. So book now and welcome!

Guest favourite

Home

4.85 out of 5 average rating, 181 reviews

Authentic Florida Bungalow near Downtown and Beach

Revisit the charm of old Florida in this 1943 cottage that has been lovingly restored. Relax on the indoor screened porch with a book or a game of cards. New air conditioning, beautiful quartz countertop in kitchen with newer appliances.Super comfy king size bed and full beds will sleep up to 4 in 2 bedrooms. Fabulous location with only 16 blocks to downtown, 10 minutes to St. Armands Circle, beautiful Lido Key . Directly on bus line for public transportation and 10 minutes to SRQ airport.

Guest favourite

Guest suite

4.99 out of 5 average rating, 148 reviews

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

Guest favourite

Guest house

4.8 out of 5 average rating, 260 reviews

Sarasota Getaway Guest House

Fully private & not shared with others Seasonal rates commence Nov 1 2023 - April 30, 2024 Longer Term Lower Rate Rentals commence May 1, 2024 - Nov 24 (Long Term rental rates available - please contact) Enjoy the luxuries of staying in the Gillispie Park area Dog Park, Tennis, Pickleball...... Walking distance to downtown where guests can find wonderful dining, entertainment, Saturday morning Farmers Market and much more Close to beaches and Arts and Entertainment and St. Armands Circle

Guest favourite

Rental unit

4.88 out of 5 average rating, 135 reviews

Downtown Apartment w/ Pool, Gym, & Coworking 329

This 2/2 apartment features an oversized kitchen with island, slider with views of Downtown. Primary has a king bed and en-suite bathroom. 2nd bedroom has a twin bed with twin trundle. Shared amenities include: gym; sunset deck; massive roof deck with heated pool; gazebo with big-screen TV, fireplace, wet bar, dog run and access to the adjacent Cowork office space building. Also on-site is Motoneko Cafe, a full-service coffee/ramen shop that also serves tea, espresso drinks, and snacks.

Guest favourite

Guest suite

4.92 out of 5 average rating, 392 reviews

SUPER CLEAN 100% Private Downtown Location

A very private, quiet and secure space with a new comfortable Queen size bed, best of linens, 100% private attached bathroom and shower. Walk to downtown, waterfront and Payne Park. Complimentary bicycles, beach cooler, beach towels and umbrella! 100 Meg WiFi, large desk, LED TV. Delightful husband/wife "Superhosts" tend to your every need including complimentary bottled water, Starbucks coffee and Bigelow tea. We utilize the Airbnb and State of Florida anti-bacterial cleaning protocols.

Guest favourite

Home

4.92 out of 5 average rating, 284 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.

Superhost

Rental unit

4.81 out of 5 average rating, 312 reviews

Fun Hip Walkable Area by Opera/Water - Studio Apt.

Perfect for those on-the-go or planning to rest in bed & read; this small studio, has cuteness, w/amenities, full-size bed, coffee maker/small refrigerator/small microwave, closet with hangers and small bureau, tiled bathroom, books, hardwood floors, fan and ductless air/heat. Petite and best for one person but two if they love to snuggle. Historic area with shopping/dining/dancing, theaters, comedy club, markets, opera, free local transportation, Bayfront marina, tiki bar+more!

Guest favourite

Guest house

4.9 out of 5 average rating, 131 reviews

Perfect Florida location: Craftsman Carriage House

Beautiful, recently built accessory dwelling in downtown Sarasota designed to match and complement our historic 1920s bungalow main house, which can be booked separately on AirBnB. The 1BR/1BA carriage house apartment has all modern amenities, with a dedicated garage parking spot and a lovely outdoor porch. The carriage house features Craftsman-style details and is available for short- or long-term stays. Locally-based property management team on-call to ensure a pleasant stay.

Guest favourite

Guest house

4.99 out of 5 average rating, 132 reviews

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!