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Results: 42 Rentals

  • Gillespie Park Modern
    From $60 per night (USD)

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    Gillespie Park Modern

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This new construction 1,350 SF apartment is part of an architect's own modern property at the heart of Gillespie Park. ...

    From $60 per night (USD)

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  • Sapphire Cottage, Sarasota FL
    From $685 per night (USD)

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    Sapphire Cottage, Sarasota FL

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    You are encouraged to verify property ownership. SarasotaCottageRentals Nestled away among the palms, bamboo and jaca ...

    From $685 per night (USD)

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  • The Beautiful Sarasota Nest
    From $50 per night (USD)

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    The Beautiful Sarasota "Nest"

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Sarasota named one of ‘10 best U.S. beach towns to live in’ by Travel + Leisure magazine A Paradise hideaway "THE SARA ...

    From $50 per night (USD)

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  • Historic Herald Square
    From $135 per night (USD)

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    Historic Herald Square

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This is a small room with cuteness and amenities, poster bed with space to store underneath, coffee maker/small refriger ...

    From $135 per night (USD)

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  • Sweet Rosemary Townhome
    From $50 per night (USD)

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    Sweet Rosemary Townhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our Sweet Rosemary Townhome -- a 2 bedroom, 2 bath split level condo in the historic and trending Rosemary District of D ...

    From $50 per night (USD)

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  • Historic Herald Square #2
    From $184 per night (USD)

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    Historic Herald Square #2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publi ...

    From $184 per night (USD)

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  • Historic Herald Square #11
    From $60 per night (USD)

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    Historic Herald Square #11

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Super cute, secure and private in downtown Sarasota. Queen sized bed and sofa with private bathroom/shower. Located abov ...

    From $60 per night (USD)

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  • Historic Herald Square #5
    From $184 per night (USD)

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    Historic Herald Square #5

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publi ...

    From $184 per night (USD)

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  • Carriage House
    From $84 per night (USD)

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    Carriage House

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Laurel Park is the coolest neighborhood in downtown Sarasota. The Carriage House is a quiet oasis ideally situated in t ...

    From $84 per night (USD)

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  • Turquoise Cottage, Sarasota FL
    From $435 per night (USD)

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    Turquoise Cottage, Sarasota FL

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    PLEASE VISIT THE SARASOTA TAX ASSESSOR'S WEB PAGE TO CONFIRM THE LEGITIMATE OWNER OF A PROPERTY YOU'RE INTERESTED IN. MA ...

    From $435 per night (USD)

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  • Golden Cottage, Sarasota FL
    From $430 per night (USD)

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    Golden Cottage, Sarasota FL

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Historic Sarasota Cottages Meets Key West Cool ~ Meets Shabby Chic. Sarasota Cottage Rentals are reserved by calendar mo ...

    From $430 per night (USD)

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  • Historic Herald Square #1
    From $218 per night (USD)

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    Historic Herald Square #1

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publi ...

    From $218 per night (USD)

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  • Burns Court
    From $259 per night (USD)

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    Burns Court

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Adorable 2 Bedroom, 1 Bath house in historic downtown Sarasota on famous Burns Court. The house is full of light with f ...

    From $259 per night (USD)

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  • Mermaid Apartment
    From $310 per night (USD)

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    Mermaid Apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    In an Mediterranean Revival home, light and airy, one bedroom above separate garage with bath and full kitchen. Wooden ...

    From $310 per night (USD)

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  • Villa Rosa
    From $100 per night (USD)

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    Villa Rosa

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Please Read the entire descriptions and additional information about our propriety. A spacious space to relax for two. ...

    From $100 per night (USD)

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  • Quiet Oasis In The City
    From $94 per night (USD)

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    Quiet Oasis In The City

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Nestled in the heart of downtown Sarasota, this artist colony consists of only a handful of homes linked together by wal ...

    From $94 per night (USD)

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  • Downtown Sarasota Luxury
    From $217 per night (USD)

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    Downtown Sarasota Luxury

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This beautiful condominium has been renovated 100% from top to bottom. Located next door to the Ritz Carlton with gorg ...

    From $217 per night (USD)

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  • 
The Cottage Next Door Sarasota Downtown location
    From $70 per night (USD)

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    The Cottage Next Door Sarasota Downtown location

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Recently restored 1925 cottage nestled in the heart of Sarasota's newest and most desirable downtown neighborhood and ju ...

    From $70 per night (USD)

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  • The Loft
    From $50 per night (USD)

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    The Loft

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    COVID CLEANING PROTOCOLS!! To put your mind at ease, we have a professional cleaning company that thoroughly cleans and ...

    From $50 per night (USD)

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  • Historic Herald Square #3
    From $75 per night (USD)

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    Historic Herald Square #3

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publi ...

    From $75 per night (USD)

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  • Beautifully decorated 1bdrm carriage house - 8 min walk to downtown Sarasota
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    Beautifully decorated 1bdrm carriage house - 8 min walk to downtown Sarasota

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Three-year-old private carriage house above garage with brand new furnishings, new paint and own deck sitting area. Loca ...

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  • Peacock on the Point  (#4/POP)
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    Peacock on the Point (#4/POP)

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    •*´¨`*•.¸¸.•*´¨This listing is for one cottage only - "Pearl Peacock/#4" ¸.•´¨`*•.¸¸.•*¨`*•.¸¸.• ^◕‿◕^ Hot Tub Ideal fo ...

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  • Central Park II Condominiums
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    Central Park II Condominiums

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Ground floor unit (No Stairs), sleeps 3 comfortably (2 on the queen bed in the bedroom and 1 on the queen sleep sofa i ...

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  • Old timer 1259er
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    Old timer 1259er

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Built in 1911, Downtown Sarasota historic Victorian-Style single family home sleeps six. Walk to downtown, theater, Shop ...

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  • 1350 Main St. Sarasota, Florida
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    1350 Main St. Sarasota, Florida

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Luxury 10th floor Condo in Sarasota’s best downtown building in best downtown location- 1 bedroom, 1.5 baths, fully furn ...

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  • 1670 Laurel Street - Unit 202
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    1670 Laurel Street - Unit 202

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Spacious 2 Bedroom, 1 Bath located in the charming Historic Laurel Park area of downtown Sarasota. Laurel Park is conve ...

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  • Harbor View Condominiums
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    Harbor View Condominiums

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    This spacious 1,900+ square foot unit has floor to ceiling windows so you won’t miss the beautiful wildlife all around y ...

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  • Sarasota Condo - 2BR, 2.5BA
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    Sarasota Condo - 2BR, 2.5BA

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    A short walk to Selby Gardens and historic downtown Sarasota full of shopping, restaurants, and Southside Village is les ...

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  • Villa Jasmine 3-9 month rental
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    Villa Jasmine 3-9 month rental

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Fabulous remodeled Villa Jasmine offers French doors to 2 private balconies for grilling, relaxing. Beautiful views of l ...

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  • Downtown Sarasota Townhouse
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    Downtown Sarasota Townhouse

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    This is a 1000 square foot newly renovated 2 bedroom, 1 bath, 1 car garage town-home located in Sarasota downtown, walki ...

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  • Vintage Main Street Loft Apartment
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    Vintage Main Street Loft Apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stay in our totally refurbished, circa 1920 loft apartment. Our vintage loft apartment is perfectly situated in the hear ...

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  • DT home 10 m. drive from beach
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    DT home 10 m. drive from beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    In the heart of the Rosemary District, this bright and spacious private home is a 10 minute drive to Lido Beaches and wi ...

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  • Vintage Gillespie Park Bungalow
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    Vintage Gillespie Park Bungalow

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Pinkie Flamingo Welcomes You To Gillespie Park Vintage Bungalow! King/Queen/DaybedPlusTrundle Old Florida charm plus d ...

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  • Hazel's Hideaway
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    Hazel's Hideaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Pinkie Flamingo Welcomes You To Hazel's Hideaway! Three month (90 Day) Min For 2020 Season. Just nine blocks from Saras ...

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  • Sarasota Apartment in Downtown
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    Sarasota Apartment in Downtown

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses, and of course the #1 Beach in the ...

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  • Sarasota Downtown Apartment
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    Sarasota Downtown Apartment

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Located in the heart of Sarasota City, just minutes to shopping, dining, golf courses, and of course the #1 Beach in the ...

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  • Sarasota Downtown Apartment
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    Sarasota Downtown Apartment

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    This is a 1000 square foot newly renovated 2 bedroom, 1 bath, 1 car garage town-home located in Sarasota downtown, walki ...

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  • Peacock on the Point (POP/#2)
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    Peacock on the Point (POP/#2)

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    •*´¨`*•.¸¸.•*´This listing is for one cottage only - "Opal Peacock/#2" `*•.¸¸.•*´¨`*•.¸¸.• ^◕‿◕^Hot Tub Ideal for Star ...

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  • 1670 Laurel Street - Unit 205
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    1670 Laurel Street - Unit 205

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Spacious 2 Bedroom, 1 Bath located in the charming Historic Laurel Park area of downtown Sarasota. Laurel Park is conve ...

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  • Zen-Inspired House in Downtown Sarasota
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    Zen-Inspired House in Downtown Sarasota

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Our vacation rental is located in downtown Sarasota with 2 Bedrooms and 2 Bathrooms with a large living area with 20' ce ...

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  • 1670 Laurel Street - Unit 204
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    1670 Laurel Street - Unit 204

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Spacious 2 Bedroom, 1 Bath located in the charming Historic Laurel Park area of downtown Sarasota. Laurel Park is conve ...

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  • 1670 Laurel Street - Unit 201
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    1670 Laurel Street - Unit 201

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Spacious 2 Bedroom, 1 Bath located in the charming Historic Laurel Park area of downtown Sarasota. Laurel Park is conve ...

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