Holiday houses 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

Townhouse in Sarasota

4.95 out of 5 average rating, 329 reviews

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!

7–14 May

$255 NZD per night

Guest favourite

Guest suite in Sarasota

4.89 out of 5 average rating, 109 reviews

Downtown privacy, beaches and nightlife all around

For the couple (or individual) who wants a fabulous private home and is in a centrally-located space in downtown Sarasota. Where the beaches meet the nightlife (Legacy Trail is 5 short blocks away, pickle ball 3 and Robarts Arena 2), this separate In-Law Suite has its own entrance, private patio and lots of space (1,000 sq. feet). 2 bikes and beach items for use are: chairs, umbrellas, noodles and coolers. The washer/dryer is attached, high-speed internet/cable; there is a gas grill, 2 tvs

16–23 May

$269 NZD per night

Guest favourite

Home in Laurel Park

4.97 out of 5 average rating, 108 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!

14–21 Jun

$375 NZD per night

Guest favourite

Guest suite in Downtown Sarasota

4.9 out of 5 average rating, 360 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 tub 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.

4–11 Oct

$158 NZD per night

Guest favourite

Guesthouse in Sarasota

4.78 out of 5 average rating, 229 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

17–24 Sep

$227 NZD per night

Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 111 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Newly renovated cozy home with all new furnishings and appliances. 2 bedrooms 1 bathroom with an eat in kitchen, sun room, and comfy living room. Stream shows or work virtually with our high speed WIFI. Grab the beach chairs and umbrella to enjoy Lido Key or Siesta Key Beaches both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the backyard. Several golf courses near-by or catch Orioles spring training at Ed Smith stadium within walking distance.

27 Jul – 3 Aug

$242 NZD per night

Guest favourite

Cottage in Sarasota

4.94 out of 5 average rating, 137 reviews

Sea-esta Cottage-cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Fresh Market & Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

4–11 Sep

$252 NZD per night

Guest favourite

Guesthouse in Rosemary District

4.91 out of 5 average rating, 113 reviews

Perfect Florida location: Craftsman Carriage House

Beautiful, new construction 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.

16–23 Nov

$269 NZD per night

Guest favourite

Guest suite in Indian Beach-Sapphire Shores

4.97 out of 5 average rating, 290 reviews

Mid-Century Suite w/ Private Entrance

Cute master suite w/ private bathroom and private entrance through backyard (no access to main house- think "mother in law suite"). Private and no access to rest of home. Self check in w/ coded lock. Lanai has washer dryer and seating area. Mini fridge (w/ small freezer), microwave and nespresso machine, water kettle. Filtered water provided. TV w/ Netflix. Wifi. Queen bed. Small desk. Private bathroom w/ bidet. Outdoor sink and shower (cold only).

12–19 Jul

$192 NZD per night

Guest favourite

Guesthouse in Sarasota

4.99 out of 5 average rating, 129 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!

13–20 Nov

$277 NZD per night

Guest favourite

Townhouse in Sarasota

4.96 out of 5 average rating, 139 reviews

Upgraded, spacious duplex in Sarasota!

Welcome to our home in Sarasota which is back on Airbnb after a 3 year hiatus! It's a beautiful, comfortable and well designed space, close to everything Sarasota has to offer. You are close to all the beaches, downtown Sarasota, SRQ Airport, Ringling museum and did I say beaches! I absolutely loved living here and I hope you find Sarasota to be a really enjoyable place.

13–20 Jun

$233 NZD per night

Guest favourite

Apartment in Sarasota

4.92 out of 5 average rating, 251 reviews

The Tangerine Apart (Near Downtown/ Spacious)

Escape to this delightful attached apartment with private entrance and parking. Enjoy a bright, spacious interior with a small kitchen and dishwasher. Explore downtown Sarasota, Siesta Key (7.2 mi), and Lido Beach (5.7 mi). Access Pinecraft and Amish dining. Accommodate guests with a queen mattress and comfy couch. Your Sarasota retreat awaits.

28 Aug – 4 Sep

$186 NZD per night