Holiday rentals in Downtown, Sarasota

4.98 out of 5 average rating, 130 reviews

The Sweet Spot! Walk to DT & Free Trolley to Beach

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 a just a short walking distance to some of the best downtown dining, shopping, arts venues and the renowned Selby Gardens. Take the free Breeze Trolley to Siesta Key and Lido beach. Relax in the private outdoor courtyard. It's is the perfect place for a couple's getaway, a family vacation, or a long term stay. So book now and welcome!

4.95 out of 5 average rating, 367 reviews

Townhouse in Sarasota

Peacock🦚1/2 m Walk to Downtown #TheTropicalNut ☀️🥳👙

You are safe with me!Enhanced cleaning protocol in place- as per Airbnb guidelines. Welcome! Be yourself! A five star stay, guaranteed. You WILL be happy here! Special occasion? My favorite. I like doing special things for special people. Courtyard w/ lounge chairs, tiki bar, pond & cafe seating! Queen bed and a pullout couch with new mattress! A 1/2 m walk to downtown. 1 of 2 upstairs apartments at The Tropical Nut! We aim to please! No-regret-booking! Will consider-if asked-pets of all kinds!

4.83 out of 5 average rating, 316 reviews

Guest house in Sarasota

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 suite in Downtown Sarasota

4.92 out of 5 average rating, 423 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 house in Downtown Sarasota

4.97 out of 5 average rating, 461 reviews

Quick and Easy Walk Downtown - Tons of Amenities

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

Flat in Downtown Sarasota

4.81 out of 5 average rating, 322 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!

4.93 out of 5 average rating, 215 reviews

Guest suite in Sarasota

MG Tropical Stay. With private entrance and patio.

Welcome to our one year old Guest Room.(Adults only). The attached Modern open concept studio style room is all yours with your own: kitchennete, bedroom, bathroom, and secluded patio! no shared spaces at all. With private entrance and two cars parking space. Quiet location -Spotless upon arrival We are welcoming you to our place! Location is 3.8 miles from downtown 7.9 miles from Lido Key Beach and less than 5 miles from Main Mall, UTC Shopping, and Restaurants areas.

Flat in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 142 reviews

Free Early Chk-in, Super Clean, Free Parking,Bikes

Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb property on the main road 1 mile from downtown Sarasota. Discover over 60 enticing amenities, from a secure room safe to a luxurious, indulgent bed. Just a stone's throw away from downtown Sarasota, Lido Beach, and essential amenities like grocery stores and pharmacies, our corner apartment with a dazzling wrap-around patio is your perfect hideaway. Bicycles at your disposal. Book now

4.92 out of 5 average rating, 108 reviews

Rhodes Studio Retreat -close to Beaches & Downtown

Experience pure elegance in this newly renovated studio retreat. With a private entrance, it comfortably accommodates 3 guests (2 on the bed, 1 on the couch). Enjoy dedicated parking, a full bath, plush queen bed, cozy couch, and a well-equipped kitchenette. Nestled in a tranquil locale near downtown Sarasota, this oasis offers easy access to urban delights. Siesta Beach is just 8.7 miles away, while Lido Beach beckons at 5.8 miles. Your ultimate escape begins here!

Guest house in Downtown Sarasota

4.89 out of 5 average rating, 123 reviews

City Garden Cottage

City Garden Cottage is a cozy and comfortable cottage located in the quiet Laurel Park neighborhood in Sarasota, only a few blocks from downtown. The studio is surrounded by lush gardens and trees. Inside you will find a kitchenette, equipped with a coffee maker, toaster, refrigerator, and hot plate. The studio also has a flat-screen TV, a queen bed & private bathroom. There is also shared use a gas grill and fire pit included with the rental.

4.99 out of 5 average rating, 140 reviews

Guest house in Sarasota

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!

4.99 out of 5 average rating, 150 reviews

Studio Minutes to Siesta key, Lido Key, and SMH!

Enjoy sunny Sarasota, FL in our studio apartment. Located between Siesta Key and Lido Key. You can walk to Southside Village, Sarasota Memorial Hospital (SMH) and Arlington Park. Enjoy the beautiful neighborhood and easy access to Legacy Trail. Approximate driving times to popular local destinations: Siesta Key - 10 minutes Lido Key - 14 minutes SRQ airport - 15 minutes St Armands - 10 minutes Downtown - 7 minutes

Holiday rentals for every style

Get the amount of space that is right for you

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Convenient locations with everyday essentials

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Popular amenities for Downtown, Sarasota holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Downtown, Sarasota's top sights

Marie Selby Botanical Gardens276 locals recommend

Van Wezel Performing Arts Hall47 locals recommend

Sarasota Farmers Market76 locals recommend

Other great holiday rentals in Downtown, Sarasota

Home in Downtown Sarasota

4.74 out of 5 average rating, 148 reviews

Bright Bungalow near Downtown, Siesta & St Armands

DesireeRating, 5 stars2 weeks ago

Perfect stay! My husband and I are very big on communication, and cleanliness and this property surpasses our expectations. We had everything we needed, plus some! Plenty of room for our family of 4. Usually staying at a hotel room we are cramped and try to stay out of the room and find things to do so we aren't "held up" in the room. Staying here, we actually spent a whole day at the house and enjoyed it immensely! We were close to a beautiful walking trail so we were able to stay active while on vacation, I will say be careful walking late at night (our favorite time to walk) because electric scooters fly through the walking trail and might scare you (can not confirm or deny if this happened to me ha ha!) Within walking distance of a beautiful park, I believe it was called Payne Park! It was so whimsical, and calm! There is laundry facilities on site so we were able to do our laundry so we weren't traveling with soiled clothing. Back yard was perfect size for our kids, and relaxing!

Superhost

Home in Downtown Sarasota

4.82 out of 5 average rating, 22 reviews

Fully Equipped Beach Home Near Beaches/Downtown

LesiaRating, 5 stars3 weeks ago

I had a wonderful stay at Giovanny’s and Catherine’s place! The house was clean, comfortable, and had everything I needed. The location was convenient, and the check-in process was smooth. Communication with the hosts was clear and friendly. I really appreciated the cozy atmosphere and attention to detail. I would definitely stay here again and highly recommend it to others. Thank you for a great experience!

4.98 out of 5 average rating, 64 reviews

Modern coastal downtown home w/saltwater pool

KellyRating, 5 stars1 day ago

Matt’s place was perfect for our anniversary trip. He was proactive in his responses and checked in on us once we got settled. We didn’t have to use the whole place for just us two but had we brought our kids, there would have been plenty of room. The place is close to the beaches, dining spots, and shopping. Will definitely return in the future.

4.93 out of 5 average rating, 70 reviews

Guest house in Sarasota

Downtown Sarasota Guest House

MelissaRating, 5 stars1 month ago

We had such a great stay at Greg’s place! It was very clean and it was close to all that we wanted to do. It’s 10 minutes from St.Armond’s circle and Lido beach which is exactly what I wanted. I’m so glad I chose to stay at Greg’s Airbnb. A great find and lovely spot!

4.95 out of 5 average rating, 58 reviews

Downtown, Pets, 2-Car Garage, Beach & St. Armands

KristiRating, 5 stars2 weeks ago

We had a fantastic stay at Melissa’s beautiful home in Sarasota! I visited with a friend and our two teenage boys, and the house was perfect for us. It was absolutely immaculate and thoughtfully stocked with everything we needed — the kitchen had all the cooking essentials, and Melissa even left goody bags in each bathroom, plus laundry detergent, which was a great touch. The closets were huge — perfect for unpacking and settling in — and the master bedroom and bathroom felt truly 5-star. So spacious, comfortable, and luxurious! Melissa was incredibly responsive and helpful any time I reached out — always quick to reply and very kind. The home is in a safe, quiet neighborhood and within walking distance to a lovely park and dog park. I highly recommend staying here. Don’t hesitate to book — you won’t be disappointed!

4.76 out of 5 average rating, 164 reviews

Private apartment w/King bed|kitchen|near beaches

GabeRating, 5 stars2 weeks ago

This Airbnb was a great one! It had everything that was listed , it was clean , and a perfect distance to the beach. We would definitely stay here again!

4.96 out of 5 average rating, 27 reviews

Pied-a-Terre

MalgorzataRating, 5 stars3 weeks ago

Place is immaculate , and it feels like home not rental. I highly recommend it. It's also in phenomenal neighborhood, close walk/ ride to downtown.