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Houses for Rent in Cherokee Park, Sarasota, FL

Average rent

$4,800

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1773 Harmony Ln - Photo 1 of 1

5d+ ago

House for rent in Sarasota

Single Family Residence - SARASOTA, FL

1773 Harmony Ln, Sarasota, FL 34239

In-unit laundry | Outdoor space | Furnished

2 beds

2 baths

$5,000

House for rent

Description

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

1865 Orchid St - Photo 1 of 1

5d+ ago

South Poinsettia house for rent in Sarasota

Single Family Residence - SARASOTA, FL

1865 Orchid St, Sarasota, FL 34239

In-unit laundry | Garage parking | Swimming pool

4 beds

3 baths

$7,500

House for rent

Description

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

3700 S Osprey Ave #212 - Photo 1 of 1

5d+ ago

Townhouse for rent in Sarasota

3700 S Osprey Avenue #212 - 212

3700 S Osprey Ave #212, Sarasota, FL 34239

Air conditioning | Central heat | Hardwood floor

1 bed

1 bath

$1,395

House for rent

Available Aug 1

Description

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.

2164 Bougainvillea St - Photo 1 of 1

1d ago

House for rent in Sarasota

Updated classic Florida bungalow-style home - 5 min from water

2164 Bougainvillea St, Sarasota, FL 34239

In-unit laundry | Outdoor space | Storage

2 beds

1 bath

$2,600

$2,500

Price drop

House for rent

Available Jun 21

Description

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

1701 Siesta Dr #1 - Photo 1 of 1

5d+ ago

House for rent in Sarasota

1701 Siesta Drive - FURNISHED - 1

1701 Siesta Dr #1, Sarasota, FL 34239

2 beds

2 baths

$2,800

House for rent

Available Jan 1

3512 S School Ave - Photo 1 of 1

5d+ ago

South Gate house for rent in Southgate

2 beds

2 baths

$2,200

House for rent

Description

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:

Nearby rental good for eco-living

Nearby rental good for pet owners

1537 Siesta Dr - Photo 1 of 1

5d+ ago

House for rent in Sarasota

Single Family Residence - SARASOTA, FL

1537 Siesta Dr, Sarasota, FL 34239

In-unit laundry | Outdoor space | Garage parking

4 beds

5 baths

$20,000

$18,500

Price drop

House for rent

Description

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

1738 Siesta Dr - Photo 1 of 1

5d+ ago

Granada house for rent in Sarasota

Single Family Residence - SARASOTA, FL

1738 Siesta Dr, Sarasota, FL 34239

In-unit laundry | Outdoor space | Garage parking

4 beds

2.5 baths

$6,500

House for rent

Description

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

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2216 Webber St #C - Photo 1 of 1

5d+ ago

House for rent in Sarasota

Single Family Residence - SARASOTA, FL

2216 Webber St #C, Sarasota, FL 34239

In-unit laundry | Outdoor space | Dishwasher

2 beds

1 bath

$1,550

House for rent

Description

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

1701 Siesta Dr - Photo 1 of 1

5d+ ago

House for rent in Sarasota

Single Family Residence - SARASOTA, FL

1701 Siesta Dr, Sarasota, FL 34239

In-unit laundry | Outdoor space | Garage parking

2 beds

1 bath

$2,800

House for rent

Description

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.

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2084 Grove St #B - Photo 1 of 1

5d+ ago

Arlington Park house for rent in Sarasota

Single Family Residence - SARASOTA, FL

2084 Grove St #B, Sarasota, FL 34239

In-unit laundry | Outdoor space | Swimming pool

1 bed

1 bath

$2,000

House for rent

Description

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.

1712 Siesta Dr #NA - Photo 1 of 1

5d+ ago

Granada house for rent in Sarasota

$2,500 - 2 Bedroom 1 Bathroom House In Sarasota With Great Amenities

1712 Siesta Dr #NA, Sarasota, FL 34239

In-unit laundry | Outdoor space | Assigned parking

2 beds

1 bath

$2,500

House for rent

Available May 1

Description

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.

2302 Hyde Park St - Photo 1 of 1

5d+ ago

Arlington Park house for rent in Sarasota

2302HydePark - 234-JAA

2302 Hyde Park St, Sarasota, FL 34239

In-unit laundry | Storage | Garage parking

3 beds

2 baths

$3,400

House for rent

Available May 11

Description

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

2302 Hyde Park St #NA - Photo 1 of 1

5d+ ago

Arlington Park house for rent in Sarasota

3 Bedroom 2 Bathroom House In Downtown Sarasota

2302 Hyde Park St #NA, Sarasota, FL 34239

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$3,400

House for rent

Available Mar 2

Description

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

2065 Goldenrod St - Photo 1 of 1
New construction

5d+ ago

House for rent in Sarasota

Single Family Residence - SARASOTA, FL

2065 Goldenrod St, Sarasota, FL 34239

In-unit laundry | Outdoor space | Garage parking

6 beds

7 baths

$20,000

House for rent

Description

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

1725 Bonita Ct - Photo 1 of 1

5d+ ago

House for rent in Sarasota

Single Family Residence - SARASOTA, FL

1725 Bonita Ct, Sarasota, FL 34239

In-unit laundry | Outdoor space | Garage parking

4 beds

3.5 baths

$15,000

House for rent

Description

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

2256 Hyde Park St #NA - Photo 1 of 1

5d+ ago

Arlington Park house for rent in Sarasota

$2,500 - 2 Bedroom 1 Bathroom House in desired Hospital area

2256 Hyde Park St #NA, Sarasota, FL 34239

In-unit laundry | Outdoor space | Assigned parking

2 beds

1 bath

$2,500

House for rent

Available Jan 5

Description

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.

2066 Roselawn St - Photo 1 of 1

5d+ ago

Townhouse for rent in Sarasota

2066 Roselawn St, Sarasota, FL 34231

In-unit laundry | Outdoor space | Garage parking

4 beds

3.5 baths

$2,995

House for rent

Description

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

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Listings within 5 miles
3919 Roberts Point Rd - Photo 1 of 1

5d+ ago

Siesta house for rent in Siesta Key

3919 Roberts Point Rd, Siesta Key, FL 34242

In-unit laundry | Outdoor space | Garage parking

4 beds

2.5 baths

$9,275

House for rent

Description

Located on Siesta Key, this 2-story home is available NOW & FURNISHED for an ANNUAL LEASE. The kitchen flows seamlessly with an OPEN LAYOUT into the expansive living and dining areas filled with NATURAL LIGHT from the large sliding glass doors opening to the SCREENED-IN LANAI. The POOL & HOT TUB/SPA, also screened-in, are framed by lush TROPICAL LANDSCAPING including lemon, avocado, banana and mango trees! The COVERED PATIO space is ideal for sunset dinners, quiet mornings, or year-round relaxation in the coastal breeze. A SUN SHADE SCREEN is installed as well for maxim

2314 Loma Linda St - Photo 1 of 1

5d+ ago

Arlington Park house for rent in Sarasota

3 Bedroom Pet-Friendly Home in Sarasota, FL with Main Street Renewal

2314 Loma Linda St, Sarasota, FL 34239

Swimming pool

3 beds

2 baths

$2,485

House for rent

Description

Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply. We do not advertise on or ask for payments via check, cash, wire transfer, or cash apps. Contact us to schedule a showing.

250 Robin Dr - Photo 1 of 1

5d+ ago

Bird Key house for rent in Sarasota

Luxury Furnished Bird Key Residence 250 Robin Drive, Sarasota, FL

250 Robin Dr, Sarasota, FL 34236

In-unit laundry | Outdoor space | Garage parking

3 beds

3 baths

$8,500

House for rent

Available Aug 3

Description

Property Id: 2598368 Experience the Bird Key lifestyle from this beautifully furnished residence in one of Sarasota's most prestigious island communities. Ideally located within walking distance of Bird Key Park, St. Armands Circle, the iconic Ringling Bridge, and downtown Sarasota, this exceptional home places dining, shopping, beaches, boating, and cultural attractions just moments away. Sarasota Memorial Hospital and Sarasota-Bradenton International Airport are only a short drive away. Nestled on a lushly landscaped lot, this approximately 2,500-square-foot home offers

376 W Royal Flamingo Dr - Photo 1 of 1

5d+ ago

Bird Key house for rent in Sarasota

Single Family Residence - SARASOTA, FL

376 W Royal Flamingo Dr, Sarasota, FL 34236

In-unit laundry | Garage parking | Swimming pool

3 beds

3.5 baths

$10,000

$9,000

Price drop

House for rent

Description

Property Status: Active Lovely Bird Key home is available for a short term rental. This turnkey furnished, one story home at the end of a cul-de sac has stunning open intracoastal views of Lido Key, Big Pass and Otter Key. The 3 bedroom, 3.5 bathroom home has a large living room, separate dining, kitchen with island, breakfast nook and lots of counter and cabinet space for cooking and entertaining. All bedrooms are spacious and allow you to really settle in. The house is full of light from windows all open to the water views. Sliding glass doors in the living room lead to

115 Edmondson Ave - Photo 1 of 1

5d+ ago

Siesta house for rent in Siesta Key

Single Family Residence - SARASOTA, FL

115 Edmondson Ave, Siesta Key, FL 34242

In-unit laundry | Swimming pool | High ceilings

5 beds

5 baths

$17,000

House for rent

Description

Property Status: Active Experience luxury coastal living just moments from world-famous Siesta Key Beach. This exceptional 5-bedroom, 5-bath residence offers approximately 3,248 SF of beautifully designed living space with an open and inviting floor plan perfect for entertaining and everyday comfort. The home features spacious bedrooms, abundant natural light, multiple gathering areas, two full kitchens, two laundry rooms, imported Italian tile throughout, USB-equipped outlets throughout the home, and designer dimmable lighting that enhances the modern coastal ambiance. Re

4205 Augustine Ave - Photo 1 of 1

5d+ ago

House for rent in Sarasota

Single Family Residence - SARASOTA, FL

4205 Augustine Ave, Sarasota, FL 34231

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$2,950

House for rent

Description

Property Status: Active Beautifully remodeled 3-bedroom, 2-bath home offering approximately 1,650 sq ft of open-concept living in a prime Sarasota location! This updated home features a modern kitchen with granite countertops, newer appliances, and stylishly renovated bathrooms. Additional upgrades include a tankless water heater, updated landscaping, and a spacious fenced backyard perfect for enjoying the Florida lifestyle. A storage shed provides extra space for tools, bikes, or beach gear, and lawn maintenance is included for easy living. This home is being offered unf

2587 Temple St - Photo 1 of 1
New construction

5d+ ago

Arlington Park house for rent in Sarasota

Single Family Residence - SARASOTA, FL

2587 Temple St, Sarasota, FL 34239

In-unit laundry | Outdoor space | Garage parking

4 beds

2.5 baths

$7,500

$7,000

Price drop

House for rent

Description

Property Status: Active Discover modern living at its finest in the heart of Arlington Park, one of Sarasota’s most desirable and centrally located neighborhoods. As a great BONUS,a beautiful POOL with a SPA is currently under construction and is expected to be completed in JULY. Tucked away on a private, dead-end street and situated directly across from Arlington Park, this home offers rare tranquility with immediate access to the park’s walking trails, fitness facilities, playground, pool, and tennis courts. Just minutes from downtown Sarasota, Sarasota Memorial Hospital

Showing 1 - 25 of 25 results
Home > House Rentals in Sarasota > Cherokee Park Houses For Rent
Updated: June 22, 2026

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Discover houses for rent in Cherokee Park, Sarasota, FL

🌇Available house rentals25 houses
💰Best rent deal3700 S Osprey Ave #212
🍃With outdoor space
Popular amenities, ,
🍽With dishwasher
🚗With garage parking
🏠With photos