Houses for Rent in Cherokee Park, Sarasota, FL

Property Status: Active OFF SEASON RENTAL ONLY! This west of Trail, west of Osprey home rests on the edge of Cherokee Park on a canopied street in one of the most sought-after locations in all of Sarasota—situated between the North Bridge to Siesta Key and downtown. Fully turnkey furnished and well-appointed, this is a charming two bed/two bath home perfect for experiencing the laid back Florida lifestyle. Walk to Morton's Market in Southside Village, Southside Elementary, Selby Gardens, or Bayfront Park. Be perfectly close to the bay, while not in a flood zone. Rays of su

Property Status: Active Welcome to tropical paradise! This stunning home away from home offers the perfect blend of relaxation and fun for all. Take a dip in the brand-new saltwater pool and spa, wind down by the cozy firepit. With spacious bedrooms, a fully equipped kitchen, and cozy living areas, you'll have everything you need! Distance from Siesta Key Beach: 4.5 miles Distance from downtown Sarasota: 2.7 miles Distance from St. Armand Circle and Lido Key: 5.4 miles This beautiful 4-bedroom, 3-bathroom turnkey furnished property offers a spacious and open concept layo

UNFURNISHED ANNUAL RENTAL, 1/1 with an enclosed lanai that can be used as a den. Great room floor plan, no carpets, tub/shower in bathroom, walk in closet. A cat would be permitted with a pet fee. Elevator and covered parking, ONE CAR ONLY.

Property Id: 2609014 Updated classic Florida bungalow-style home with a brand new kitchen, Mexican tiles, beautiful archways, full of natural lighting, a full-length mirrored wall and washer/dryer included -- now available for rent in the coveted Southgate community, with several million dollar properties on the block. Just a couple minutes from the North Siesta Key Bridge, enjoy modern city living with the benefit of a spacious back yard and a covered front patio and carport. Lawn maintenance included as well as access to Southgate community pool. The home is located jus

Welcome to this charming 2-bedroom, 2-bathroom home located in the highly desirable Southgate neighborhood in Sarasota! Conveniently located just minutes from Siesta Key Beach, Southgate Plaza, shopping, dining, and downtown Sarasota. This bright and spacious home features: ✔ Open floor plan with plenty of natural light ✔ Terrazzo flooring throughout ✔ Large bedrooms (both can fit king-size beds) ✔ Bonus Florida room – perfect for extra living space or a home office ✔ 1-car garage ✔ Private fenced backyard – great for relaxing or entertaining ✔ Washer/Dryer hookups Rent:

Property Status: Active Welcome to Siesta by the Bay! This turnkey luxury home features 4 ensuite bedrooms, water views of the bay, pool bath and half bath, outdoor shower, outdoor kitchen, heated pool, putting green, and 3 car garage. Enjoy a private backyard with an expansive outdoor dining area and bar with multiple areas to exercise and lounge. Located near the Siesta Key North bridge, you’re minutes from world famous beaches, downtown Sarasota, Hillview Shopping Plaza, Sarasota Memorial Hospital, fine dining, and many more popular activities that Sarasota has to offer

Property Status: Active Available June 1st, this newer (2013) “West of Trail” pool home offers an ideal opportunity to get settled ahead of the upcoming school year in the highly regarded Southside Elementary district, just a short bike ride away. Offered at $6,500/month with an annual lease preferred (6-month considered), the home provides flexibility with furnishings — available furnished or unfurnished. Elevated 22 feet above sea level in an X flood zone, it delivers both peace of mind and easy coastal living with a thoughtful layout featuring 4 bedrooms along with a ve

Property Status: Active Totally redone, 2 bedroom, 1 bath and a den house available. New kitchen, new paint, appliance, blinds etc. Back and side yard are fully fenced. Near Southside Elementary School, Southside Village shops and restaurants. A quick walking path to Westfield Siesta Key mall and Shops at Siesta Row. Near Sarasota Memorial Hospital and about 2-3 miles from downtown Sarasota. Office Phone: (941) 374-7700 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should

Property Status: Active WEST OF THE TRAIL, BUILT IN 1926! Historic home near the north bridge going to Siesta Key. Cozy and quaint historical home minutes from the Siesta Key and Hillview. Step back in time in this cozy and relaxing home. Wonderful library. Enclosed garden/courtyard. Garage not available. Non smoking. No long term rentals available. Office Phone: (941) 922-4959 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Property Status: Active This one-bedroom, one-bath furnished rental guest house is recently renovated with private entrance, fenced patio/yard area, your own free- standing HOT TUB and access to the shared POOL in the back yard! There is a stackable PRIVATE LAUNDRY conveniently located in the walk-in closet to the bedroom. The kitchenette boasts a large granite countertop with induction cooktop, refrigerator, small convection oven, icemaker, and is open to the living room that has a sofa-bed. The fold-down table can be used as a desk or pulled out from the wall to seat 4.

Amazing 2 bedroom, 1 bathroom house in Sarasota. Amenities included: central air, central heat, dishwasher, hardwood floors, stainless steel appliance, washer dryer, and yard. No Utilities included. Is not pet friendly. Date Available: May 1st 2026. $2,500/month rent. $5,000 security deposit required. Please submit the form on this page or contact Maciek at 941-400-7084 to learn more. This property is managed by a responsible landlord using Avail landlord software.

ANNUAL RENTAL – DOWNTOWN SARASOTA Welcome home to this beautifully updated 3-bedroom, 2-bath single-family residence ideally located in the heart of downtown Sarasota, just minutes from US 41, Sarasota Memorial Hospital, and the world-famous Siesta Key Beach. Nestled near Sarasota's charming historic districts, this home offers unbeatable access to restaurants, shopping, fitness options, and cultural attractions, making it perfect for those who enjoy an active and convenient lifestyle. The interior features an open and versatile layout with additional space ideal for a

ANNUAL RENTAL – DOWNTOWN SARASOTA Welcome home to this beautifully updated 3-bedroom, 2-bath single-family residence ideally located in the heart of downtown Sarasota, just minutes from US 41, Sarasota Memorial Hospital, and the world-famous Siesta Key Beach. Nestled near Sarasota's charming historic districts, this home offers unbeatable access to restaurants, shopping, fitness options, and cultural attractions, making it perfect for those who enjoy an active and convenient lifestyle. The interior features an open and versatile layout with additional space ideal for a hom

Property Status: Active Make yourself at home in this stunning brand-new getaway, where everyday living feels like a vacation. With over 3,600 square feet of beautifully designed space, this home offers all the room you need to relax, work, entertain, and truly settle into the Sarasota lifestyle. Step through the charming courtyard entrance and into bright, open living areas filled with natural light and tall ceilings, to find a comfortable layout and tasteful details that create a space that is as welcoming as it is impressive. The kitchen will quickly become your favorit

Property Status: Active This MAGNIFICENT home is nestled away in the Historic Granada private neighborhood with easy access to all amenities. 4 Bedrooms 3.5 Baths and over 3500+ square feet of elegantly finished living areas. Authentic travertine tile and maple hardwood floors, volume ceilings, solid-wood cabinetry, two-sided fireplace, chef’s kitchen, three-car garage (owner uses one bay) and cypress wood exterior ceilings. Designed for entertaining, this splendid home can easily host large gatherings with a creative layout that enhances the flow between the kitchen, dini

FOR RENT - 2256 Hyde Park St., annual lease, two bedroom, one bath, plus bonus room, living room, kitchen, detached laundry room. Carport. Fenced-in yard, southern exposure, Riverview school district. Hospital area, best location, quick to downtown, shopping, and beaches. No smokers. First, last & security deposit to move in. 941-356-5849.

This gorgeous modern townhouse boasts 4 spacious bedrooms and 3.5 bathrooms, offering ample space and comfort for a family. The kitchen is a chef's dream with GRANITE COUNTERTOPS and STAINLESS STEEL APPLIANCES. The OPEN FLOOR PLAN includes dining space and cozy living room, both featuring HIGH/VAULTED ceilings, truly a warm and inviting atmosphere. The townhouse also includes LOFT space for a dedicated office/desk space, perfect for those who work from home or homework with the kids. Upstairs has HARDWOOD FLOORS. Outside, you'll find a fully FENCED PATIO, perfect for ou