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  • Newly Renovated Classic Bungalow
    Click For Pricing

    VRBO

    Newly Renovated Classic Bungalow

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy this recently renovated bungalow in a quiet neighborhood conveniently located near beaches, museums, theaters, dow ...

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    VRBO

    Details
  • Heart of Downtown - minutes from beach
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    Expedia

    Heart of Downtown - minutes from beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Located in the heart of downtown Sarasota. 1350 Main Residential Condo is walking distance from Marina Jacks, Bayfront P ...

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    Expedia

    Details
  • Guest Suite for Beach & Dog Lovers-Best Location!
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    VRBO

    Guest Suite for Beach & Dog Lovers-Best Location!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    About this space Quiet & clean in-law suite w/ private entrance devoted to dog lovers, beach goers, or anyone looking fo ...

    Click For Pricing

    VRBO

    Details
  • The Blessing House - Htd Pool & Spa, Close to Beaches
    From $684 per night (USD)

    Expedia

    The Blessing House - Htd Pool & Spa, Close to Beaches

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to The Blessing House! This home has been beautifully renovated, designed & curated for you to be rejuvenated, ...

    From $684 per night (USD)

    Expedia

    Details
  • Centrally Located Home - 7 Miles to Siesta Key!
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    VRBO

    Centrally Located Home - 7 Miles to Siesta Key!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    11

    2,000 Sq Ft | Fire Pit | Washer & Dryer | ~7 Mi to The Ringling Museum of Art Trade your snow boots for flip flops when ...

    Click For Pricing

    VRBO

    Details
  • Luxurious home with amazing rooftop deck views
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    Expedia

    Luxurious home with amazing rooftop deck views

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    12

    Knot A Basic Beach House by Lido Key Vacations Home in Sarasota FL 34236 Vacation Rental License #: VR23-00003 Minimum s ...

    Click For Pricing

    Expedia

    Details
  • The Hideaway: 4\/2 w heated pool & Outdoor Spaces
    From $327 per night (USD)

    VRBO

    The Hideaway: 4\/2 w heated pool & Outdoor Spaces

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to the Jungle House! This family friendly and spacious home is here to serve the entire family on your visit to ...

    From $327 per night (USD)

    VRBO

    Details
  • Beach Bum Bungalow-Sarasota-2 bdrm1 bath close to Siesta Key
    From $156 per night (USD)

    Expedia

    Beach Bum Bungalow-Sarasota-2 bdrm1 bath close to Siesta Key

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our charming 'Beach Bum' vacation rental home in beautiful Sarasota, Florida only 10 minutes to Siesta Key. O ...

    From $156 per night (USD)

    Expedia

    Details
  • Sunseeker Bungalow-Great location to all things Sarasota
    From $183 per night (USD)

    VRBO

    Sunseeker Bungalow-Great location to all things Sarasota

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our charming 'Sun Seeker' vacation rental home in beautiful Sarasota, Florida only 10 minutes from Siesta Key ...

    From $183 per night (USD)

    VRBO

    Details
  • Gorgeous Remodeled 2 Bedroom Longboat Key Condo with Stunning Bay Views!
    From $290 per night (USD)

    Expedia

    Gorgeous Remodeled 2 Bedroom Longboat Key Condo with Stunning Bay Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautiful 2 bedroom/2 bath recently updated condo on Longboat Key looking over stunning Sarasota Bay. Top 3rd floor -wi ...

    From $290 per night (USD)

    Expedia

    Details
  • Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!
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    VRBO

    Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to Palm Paradise, your ultimate vacation rental nestled in the picturesque Northern part of Siesta Key Island, S ...

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    VRBO

    Details
  • Contemporary Ranch, near Siesta Key & Donwtown SRQ
    From $415 per night (USD)

    Expedia

    Contemporary Ranch, near Siesta Key & Donwtown SRQ

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Nestled in the serene neighborhood of South Gate, Siesta Key, our contemporary 3-bedroom, 2-bath oasis is the perfect bl ...

    From $415 per night (USD)

    Expedia

    Details
  • Comfortable home in charming Southgate
    From $185 per night (USD)

    VRBO

    Comfortable home in charming Southgate

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    About this space 10 minutes from Siesta Key, Downtown, Waterfront restaurants, and more. Conveniently located between tr ...

    From $185 per night (USD)

    VRBO

    Details
  • Quiet family home located centrally to beaches and downtown Sarasota
    From $165 per night (USD)

    Expedia

    Quiet family home located centrally to beaches and downtown Sarasota

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Sit on the back porch enjoying a relaxing evening after a day at the beach or out shopping downtown. Located just minut ...

    From $165 per night (USD)

    Expedia

    Details
  • Siesta Key, 2.5 miles away! Close to everything.
    From $228 per night (USD)

    VRBO

    Siesta Key, 2.5 miles away! Close to everything.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    You’re just a short drive from Siesta Key Beach, downtown Sarasota and so much more in a quiet residential neighborhood. ...

    From $228 per night (USD)

    VRBO

    Details
  • 4 Bedroom Pool House in Heart of Sarasota
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    Expedia

    4 Bedroom Pool House in Heart of Sarasota

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    When you stay at this centrally-located place, your family will be close to everything. 4 bedrooms 2 bathrooms. Beautifu ...

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    Expedia

    Details
  • 3 bedroom pool home by FVC
    From $715 per night (USD)

    VRBO

    3 bedroom pool home by FVC

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to your picturesque getaway on St. Armands Circle, where tranquility meets coastal luxury in this stunning vacat ...

    From $715 per night (USD)

    VRBO

    Details
  • Historic Bayshore Cottage walk to Bay & Ringling
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    Expedia

    Historic Bayshore Cottage walk to Bay & Ringling

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Charming and beautifully restored craftsman cottage on prestigious Bay Shore Rd, just minutes from Ringling, New College ...

    Click For Pricing

    Expedia

    Details
  • Luxe Oasis | Private Pool, In St Armands Circle, Near Lido Key Beach!
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    VRBO

    Luxe Oasis | Private Pool, In St Armands Circle, Near Lido Key Beach!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Luxe Oasis, your exclusive tropical escape on the beautiful Lido Key. Nestled just moments from the renowned ...

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    VRBO

    Details
  • This nice house is located close in a nice and safe neighborhoods and 15
    From $243 per night (USD)

    Expedia

    This nice house is located close in a nice and safe neighborhoods and 15

    Bedrooms:
    3
    Bathrooms:
    1
    Sleeps:
    6

    Cozy and spacious family house located in a nice, safe area in Sarasota, near Downtown, 5 miles away from Siesta key one ...

    From $243 per night (USD)

    Expedia

    Details
  • Sunshine Bliss Bungalow
    From $167 per night (USD)

    VRBO

    Sunshine Bliss Bungalow

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Kick back and relax in this calm, stylish space. Cozy living space, fully equipped kitchen, and comfy bedrooms await. En ...

    From $167 per night (USD)

    VRBO

    Details
  • Five Palms Indulge in a Stunning Lido Key Retreat with Private Pool, Firepit, and Steps to the Beach
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    Expedia

    Five Palms Indulge in a Stunning Lido Key Retreat with Private Pool, Firepit, and Steps to the Beach

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to Five Palms – Your Ultimate Tropical Paradise on Lido Key Welcome to Five Palms, where luxury, comfort, and t ...

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    Expedia

    Details
  • Twin Palms | Two Houses + Private Pool!
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    VRBO

    Twin Palms | Two Houses + Private Pool!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    BNB Breeze Presents: Twin Palms! This stunning 2 house oasis resides in the heart of Sarasota Florida and is located jus ...

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    VRBO

    Details
  • Waterfront Luxury - Direct Gulf Views - Resort Pool/Spa - Siesta Key Village
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    Expedia

    Waterfront Luxury - Direct Gulf Views - Resort Pool/Spa - Siesta Key Village

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    12

    Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation ex ...

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    Expedia

    Details
  • Charming 3-bedroom house in delightful Sarasota with WiFi, AC
    From $328 per night (USD)

    VRBO

    Charming 3-bedroom house in delightful Sarasota with WiFi, AC

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    A house with a private lanai and a saltwater pool offers a perfect blend of indoor and outdoor living. The lanai provide ...

    From $328 per night (USD)

    VRBO

    Details
  • Quiet peaceful home on the canal with a dock; 2 minute walk to St Armands Circle
    From $853 per night (USD)

    Expedia

    Quiet peaceful home on the canal with a dock; 2 minute walk to St Armands Circle

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    NEW RENOVATIONS/CONSTRUCTION: The home was recently purchased and renovated with all new furnishings and appliances. T ...

    From $853 per night (USD)

    Expedia

    Details
  • Penthouse #1 Oceanfront on Lido Beach! Sunrise & Sunset Views - 2 Bed 2 Bath
    From $456 per night (USD)

    VRBO

    Penthouse #1 Oceanfront on Lido Beach! Sunrise & Sunset Views - 2 Bed 2 Bath

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    This special 2 bedroom/2 bathroom Penthouse has been recently renovated with luxury in mind! Located in The Lido Beach C ...

    From $456 per night (USD)

    VRBO

    Details
  • New-Luxurious St. Armands Vacation Home, Walk to Beach, Gulf Views, Resort Pool
    From $1364 per night (USD)

    Expedia

    New-Luxurious St. Armands Vacation Home, Walk to Beach, Gulf Views, Resort Pool

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    16

    Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation ex ...

    From $1364 per night (USD)

    Expedia

    Details
  • Sunset Paradise Condo on Beach
    From $504 per night (USD)

    VRBO

    Sunset Paradise Condo on Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This unique first-floor beach front condo is located adjacent to the luxurious Ritz Carlton and Tiki Bar. Step out of yo ...

    From $504 per night (USD)

    VRBO

    Details
  • Surfside Villa | Private POOL + Sunroom!
    From $419 per night (USD)

    Expedia

    Surfside Villa | Private POOL + Sunroom!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    BNB Breeze Presents: Surfside Villa! Experience this stunning, newly-renovated home in the heart of Sarasota, located ju ...

    From $419 per night (USD)

    Expedia

    Details
  • New-Luxurious St. Armands Vacation Home, Walk to Beach, Gulf Views, Resort Pool
    From $1364 per night (USD)

    VRBO

    New-Luxurious St. Armands Vacation Home, Walk to Beach, Gulf Views, Resort Pool

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    16

    Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation ex ...

    From $1364 per night (USD)

    VRBO

    Details
  • Sunshine 2-bedroom apartment 5 mile from Siesta Beach
    From $146 per night (USD)

    Expedia

    Sunshine 2-bedroom apartment 5 mile from Siesta Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    We are located in Sarasota 5 miles from the beach and downtown, 5 miles from I-75. Close to Supermark, mover theater, an ...

    From $146 per night (USD)

    Expedia

    Details
  • Beautiful 1-bedroom condo in The Meadows, minutes from the beach, golf, shopping
    From $76 per night (USD)

    VRBO

    Beautiful 1-bedroom condo in The Meadows, minutes from the beach, golf, shopping

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in Sarasota, enjoy what this 1-bedroom condo has to offer. This welcoming property is a 2nd floor condo unit in ...

    From $76 per night (USD)

    VRBO

    Details
  • Robinhood Beach Villa
    From $204 per night (USD)

    Expedia

    Robinhood Beach Villa

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    You will feel right at home in this cozy beach villa which gives you a natural beach feeling AND adds a modern feel with ...

    From $204 per night (USD)

    Expedia

    Details
  • 2 Bedroom Lido Key Condo by FVC
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    VRBO

    2 Bedroom Lido Key Condo by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Professionally managed and offered by FL Vacation Connection. This is a spacious two bedroom condo perfectly situated t ...

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    VRBO

    Details
  • Inn on the Beach 7304 by FVC
    From $377 per night (USD)

    Expedia

    Inn on the Beach 7304 by FVC

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Your Longboat Key Retreat with Sleepy Lagoon Views by FVC Experience the pinnacle of coastal living in this beautifully ...

    From $377 per night (USD)

    Expedia

    Details
  • Bayview Paradise by FVC
    From $308 per night (USD)

    VRBO

    Bayview Paradise by FVC

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Bayview Paradise managed by Florida Vacation Connection. This spacious 4 bedroom/ 3 full baths private pool ...

    From $308 per night (USD)

    VRBO

    Details
  • Lovely 4-bedroom house in Sarasota with pool and enjoyable backyard
    From $294 per night (USD)

    VRBO

    Lovely 4-bedroom house in Sarasota with pool and enjoyable backyard

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Your cozy getaway awaits in Sarasota at this awesome house. With 4 bedrooms including 1 king bed, 2 queen beds, and 2 tw ...

    From $294 per night (USD)

    VRBO

    Details
  • Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota
    From $433 per night (USD)

    VRBO

    Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Treat yourself to an unforgettable vacation at a luxury modern villa in the perfect location of Lido Beach. Walking dist ...

    From $433 per night (USD)

    VRBO

    Details
  • Siesta Key Pool Palace - Walk to Beach
    From $1103 per night (USD)

    Expedia

    Siesta Key Pool Palace - Walk to Beach

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    12

    Bring the entire family to this serene getaway on Siesta Key! A short walk to Shell beach, this charming retreat offers ...

    From $1103 per night (USD)

    Expedia

    Details
  • Beautiful Family-sized Home in Sunny Sarasota, Florida with large backyard!
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    VRBO

    Beautiful Family-sized Home in Sunny Sarasota, Florida with large backyard!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to the recently completely renovated Blue Heron Lodge! Enjoy a serene and stunning fenced backyard paradise. You ...

    Click For Pricing

    VRBO

    Details
  • Spend a few month at the beach! 2BR/2Ba, gated beachfront condo with heated pool
    From $119 per night (USD)

    Expedia

    Spend a few month at the beach! 2BR/2Ba, gated beachfront condo with heated pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    NEW LISTING! Available for: May-July, Sept-Dec 20, and Jan-April 6. Will consider monthly for January. Contact us! This ...

    From $119 per night (USD)

    Expedia

    Details
  • The Jungle Retreat w/ Pool & Bar
    From $361 per night (USD)

    VRBO

    The Jungle Retreat w/ Pool & Bar

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This is a beautiful 2/2 on a beautiful lot with a large pool, bar, and mini put-put green. The location is truly as good ...

    From $361 per night (USD)

    VRBO

    Details
  • Inviting Sarasota Cottage: 5 Mi to Beach Access!
    From $127 per night (USD)

    Expedia

    Inviting Sarasota Cottage: 5 Mi to Beach Access!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Experience charm and comfort at this cozy Sarasota vacation rental! Boasting a walkable location with easy access to din ...

    From $127 per night (USD)

    Expedia

    Details
  • Pool house 10 mins to Siesta Key #1 Bch
    From $398 per night (USD)

    VRBO

    Pool house 10 mins to Siesta Key #1 Bch

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This 2-bedroom, 2-bath home underwent a thoughtful and complete renovation in 2020 . An open concept layout and a true F ...

    From $398 per night (USD)

    VRBO

    Details
  • Kingston Cabana | Gorgeous Condo! Pool, Near Beach
    From $349 per night (USD)

    Expedia

    Kingston Cabana | Gorgeous Condo! Pool, Near Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Experience coastal bliss & all the luxuries beach life has to offer when you stay in our ground floor Kingston ...

    From $349 per night (USD)

    Expedia

    Details
  • Private Oasis
    Click For Pricing

    VRBO

    Private Oasis

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Take in everything the vibrant city of Sarasota has to offer, pristine beaches 20 minutes away, dive into the downtown n ...

    Click For Pricing

    VRBO

    Details
  • Fabulous Coastal Pool Home
    From $1173 per night (USD)

    Expedia

    Fabulous Coastal Pool Home

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This fabulous canal-front home located on famous Lido Key is a boater's dream. This home is well appointed with outdoor ...

    From $1173 per night (USD)

    Expedia

    Details
  • Island Vibes + Modern Comfort at Lido Beach!
    From $273 per night (USD)

    VRBO

    Island Vibes + Modern Comfort at Lido Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    **Island Vibes + Modern Comfort at Lido Beach! ** Looking for the perfect island escape? You’ve found it! Welcome to ou ...

    From $273 per night (USD)

    VRBO

    Details
  • NEW Sarasota beach home {Seas the Day}
    Click For Pricing

    Expedia

    NEW Sarasota beach home {Seas the Day}

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Nestled in the heart of Sarasota "Seas the Day" awaits you. Siesta Key's white sandy beaches are a short 12 min. drive f ...

    Click For Pricing

    Expedia

    Details
  • Luxury Family Home! Great Location! Heated Pool/Spa and Games! - The Big Top
    From $932 per night (USD)

    VRBO

    Luxury Family Home! Great Location! Heated Pool/Spa and Games! - The Big Top

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    16

    The Big Top by Lido Key Vacations Sarasota FL 34236 Vacation Rental License #VR22-00043 Minimum stay duration of 7 days/ ...

    From $932 per night (USD)

    VRBO

    Details
  • Siesta key Guest House 5 star on the water Private
    From $356 per night (USD)

    Expedia

    Siesta key Guest House 5 star on the water Private

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    OK so let me make this easy for you. This Amazing spot is not like other property your looking at! Imagine this! Going t ...

    From $356 per night (USD)

    Expedia

    Details
  • Spacious Siesta Key Family Home with Private Pool – Sleeps 10!
    From $391 per night (USD)

    VRBO

    Spacious Siesta Key Family Home with Private Pool – Sleeps 10!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    4 private rooms for sleeping - 3 large bedrooms plus a private bonus room. Beautiful 2 story home with a 2 car garage ...

    From $391 per night (USD)

    VRBO

    Details
  • Siesta Key 2B 2 bath with Heated Pool! Sleeps 6 ! Relaxation & Sunshine!
    From $209 per night (USD)

    Expedia

    Siesta Key 2B 2 bath with Heated Pool! Sleeps 6 ! Relaxation & Sunshine!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Sarasota rental perfect for family and friends getaways! 10 minutes from Siesta Key Beach! OUR rental features a comfy k ...

    From $209 per night (USD)

    Expedia

    Details
  • Sleeps 10 & pet friendly #3606 Villa Franca
    From $172 per night (USD)

    VRBO

    Sleeps 10 & pet friendly #3606 Villa Franca

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    Summary: Ready to rent after hurricane Milton. You will find yourself in a cozy living room with brand new couches. Larg ...

    From $172 per night (USD)

    VRBO

    Details
  • Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!
    From $174 per night (USD)

    Expedia

    Lovely ❤ Cottage - VERY close to Siesta Beach, Downtown, Shopping and More!!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    NOTE: BOOKING JANUARY OR FEBRUARY? Please book whole months only NOT mid-month to mid-month. This time frame is a monthl ...

    From $174 per night (USD)

    Expedia

    Details
  • Relaxing 3BR/2Ba Oasis with Heated Pool.
    From $249 per night (USD)

    VRBO

    Relaxing 3BR/2Ba Oasis with Heated Pool.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to our inviting three-bedroom house, nestled on a quiet dead-end street. With its charming and friendly atmosphe ...

    From $249 per night (USD)

    VRBO

    Details
  • Recently Updated Apartment close to Siesta Key
    From $339 per night (USD)

    Expedia

    Recently Updated Apartment close to Siesta Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    A 2 bedroom, 2 bath cottage conveniently located near Siesta Dr that takes you all the way to the famous Siesta Beach an ...

    From $339 per night (USD)

    Expedia

    Details
  • Pinecraft Paradise ~ Secluded Apt in central SRQ!
    From $160 per night (USD)

    VRBO

    Pinecraft Paradise ~ Secluded Apt in central SRQ!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Looking for a relaxing retreat in sunny Sarasota? Kick back and relax in this trendy, chic apartment with a bit of coast ...

    From $160 per night (USD)

    VRBO

    Details
  • Farmhouse Flair Getaway ~ In Pinecraft Village!
    From $86 per night (USD)

    Expedia

    Farmhouse Flair Getaway ~ In Pinecraft Village!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Looking for a relaxing retreat in sunny Sarasota? Kick back and relax in this fresh, new apartment with modern farmhouse ...

    From $86 per night (USD)

    Expedia

    Details
  • WE ARE OPEN FOR BUSINESS , walk to the beach and st Armand circle
    From $197 per night (USD)

    VRBO

    WE ARE OPEN FOR BUSINESS , walk to the beach and st Armand circle

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Be sure to check out our other propertie 2086500 - Sunshine on Lido (New Listing) ++++++++++++++++++++++++++++++++++++++ ...

    From $197 per night (USD)

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    Details
  • Putting green, Rooftop Deck AND Beach/Gulf Views with Private Heated Pool/Spa.
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    Expedia

    Putting green, Rooftop Deck AND Beach/Gulf Views with Private Heated Pool/Spa.

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    16

    All Decked Out by Lido Key Vacations Home in Lido Key, FL 34236 Vacation Rental License #VR22-00028 Minimum stay durati ...

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  • Casa Lime in Pinecraft
    From $401 per night (USD)

    VRBO

    Casa Lime in Pinecraft

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    A 1 bedroom, 1 bath cottage that comfortably sleeps 3 guests. Conveniently located in central Sarasota, in the quaint Am ...

    From $401 per night (USD)

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    Details
  • King Bed ❤ Walk to St. Armand's Circle and Lido Beach in Minutes!
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    Expedia

    King Bed ❤ Walk to St. Armand's Circle and Lido Beach in Minutes!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    WOW location!!! Minutes walk to Lido Beach or Famous St. Armand's Circle for amazing restaurants and Shopping. King-Size ...

    Click For Pricing

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  • Hidden gem close to everything!!!
    From $237 per night (USD)

    VRBO

    Hidden gem close to everything!!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Our house is seated on a quiet little street close to downtown and 10 minutes to the number 1 beach siesta key 5 minutes ...

    From $237 per night (USD)

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    Details
  • Gulfview Lido Key Gem - Walk to Beach & Shops
    From $274 per night (USD)

    Expedia

    Gulfview Lido Key Gem - Walk to Beach & Shops

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beachside relaxation and upscale coastal shopping await at this 2-bedroom, 2-bath vacation rental on Lido Key! This Sara ...

    From $274 per night (USD)

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    Details
  • The Coconut House, Sarasota
    From $576 per night (USD)

    VRBO

    The Coconut House, Sarasota

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    ‘Home sweet home, away from your home’ ...Our house is newly renovated with plenty of space for larger groups. Brand ne ...

    From $576 per night (USD)

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    Details
  • Casa Lemon
    From $259 per night (USD)

    Expedia

    Casa Lemon

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A 1 bedroom, pull out couch & air mattress, 1 bath cottage that comfortably sleeps 6 guests. Conveniently located in cen ...

    From $259 per night (USD)

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    Details
  • Casa Orange
    From $300 per night (USD)

    VRBO

    Casa Orange

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    A 1 bedroom 1 bath cottage that comfortably sleeps 6 guests . Conveniently located in central Sarasota, in the quaint Am ...

    From $300 per night (USD)

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    Details
  • Casa Grapefruit
    From $521 per night (USD)

    Expedia

    Casa Grapefruit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    2 bedroom, 1 bath cottage that comfortably sleeps 6 guests. Conveniently located in central Sarasota, in the quaint Amis ...

    From $521 per night (USD)

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    Details
  • House with HEATED POOL and Outdoor Space
    From $313 per night (USD)

    VRBO

    House with HEATED POOL and Outdoor Space

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Private home with 3 bedrooms, large 2 baths, fully equipped kitchen, large living room and dining room. Washer/dryer. ...

    From $313 per night (USD)

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    Details
  • 4 bed 3 bath Waterfront Home by Ralph Twitchell
    From $442 per night (USD)

    Expedia

    4 bed 3 bath Waterfront Home by Ralph Twitchell

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Originally designed by Ralph Twitchell, one of the founding members of the Sarasota School of Architecture, this midcent ...

    From $442 per night (USD)

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    Details
  • Beachside Private Vacation Home w/ Large Heated Pool
    From $410 per night (USD)

    VRBO

    Beachside Private Vacation Home w/ Large Heated Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Come and enjoy a stress free vacation at this island paradise three bedroom two bath private home with heated pool. The ...

    From $410 per night (USD)

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    Details
  • Luxury Home W/ Pool, Spa, and Walking Distance to Beach
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    Expedia

    Luxury Home W/ Pool, Spa, and Walking Distance to Beach

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Come enjoy the relaxed vibe of Siesta Key! The beautiful white sand beaches that make Siesta Key the #1 beach in the US ...

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  • Super Clean 3 bdrm Home in Siesta Key with Boat Dock & Pool - Small Dogs Considered
    From $400 per night (USD)

    VRBO

    Super Clean 3 bdrm Home in Siesta Key with Boat Dock & Pool - Small Dogs Considered

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    7

    Bring your Boat!! Large 3 bedroom home with boat dock. Power is provided by the dock and there is a full outside shower ...

    From $400 per night (USD)

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    Details
  • Quiet Sarasota Retreat - 6 Mi to Siesta Key Beach!
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    Quiet Sarasota Retreat - 6 Mi to Siesta Key Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ensure easy access to beautiful Gulf Coast beaches when you spend your next Florida getaway at this Sarasota vacation re ...

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    Details
  • Lido Shores Sanctuary: House on Lido Key by RVA
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    VRBO

    Lido Shores Sanctuary: House on Lido Key by RVA

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to the Lido Shores Sanctuary by RVA. Located in the private community of Lido Shores, with gated beach access an ...

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    Details
  • Pool, Putting Green, Steps to Shopping, & Tons of Living Space -The Shore House
    From $1062 per night (USD)

    Expedia

    Pool, Putting Green, Steps to Shopping, & Tons of Living Space -The Shore House

    Bedrooms:
    4
    Bathrooms:
    7
    Sleeps:
    16

    The Shore House by Lido Key Vacations Sarasota FL 34236 Vacation Rental License #VR22-00033 Minimum stay duration of 7 ...

    From $1062 per night (USD)

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    Details
  • Close to Siesta Beach # 1 in Usa
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    Close to Siesta Beach # 1 in Usa

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Cute and clean one bedroom, one bath just minutes to the white sand Siesta Key Beach number ONE in USA . Close to shoppi ...

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    Details
  • Bright, cozy studio in the middle of Sarasota
    From $91 per night (USD)

    Expedia

    Bright, cozy studio in the middle of Sarasota

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Bright studio in multi family house with nice & quiet tenants. TCentrally located, near everything that offering sunny S ...

    From $91 per night (USD)

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    Details
  • Family friendly with large pool
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    Family friendly with large pool

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    This newly remodeled beach house, is perfect for families as it comfortably sleeps 13 people and is located in a peacefu ...

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    Details
  • Lido Rondy Home on Lido Key by RVA
    From $324 per night (USD)

    Expedia

    Lido Rondy Home on Lido Key by RVA

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to comfortable, Mid-Century Modern in the heart of quiet Lido Key at the Lido Rondy Home by RVA. Located just ou ...

    From $324 per night (USD)

    Expedia

    Details
  • Large and bright studio in the middle of Sarasota
    From $97 per night (USD)

    VRBO

    Large and bright studio in the middle of Sarasota

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Bright studio in multi family house with nice & quiet tenants. Centrally located, near everything that offering sunny Sa ...

    From $97 per night (USD)

    VRBO

    Details
  • Centrally located Oasis
    From $233 per night (USD)

    Expedia

    Centrally located Oasis

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Newly renovated beautiful pool house with fenced in back yard. Completely private in a very quiet neighborhood. King siz ...

    From $233 per night (USD)

    Expedia

    Details
  • Cozy 1/1 Condo Overlooking the Groves Golf Course Community Pool
    From $84 per night (USD)

    VRBO

    Cozy 1/1 Condo Overlooking the Groves Golf Course Community Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This is a charming and luminous condo of 460 sq. ft. fully furnished and equipped with great taste. It will be perfect t ...

    From $84 per night (USD)

    VRBO

    Details
  • Cozy Cabana ....walk to the beach and St Armand's Circle!
    From $266 per night (USD)

    Expedia

    Cozy Cabana ....walk to the beach and St Armand's Circle!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    On the side of the cottage you will discover a stairway leading to this recently remodeled one bedroom apartment complet ...

    From $266 per night (USD)

    Expedia

    Details
  • 🏝Tropical Siesta Key Home with Incredible Pool, Hot Tub, and Patio!
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    VRBO

    🏝Tropical Siesta Key Home with Incredible Pool, Hot Tub, and Patio!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to “High Tide”… a cozy 5 bedroom 4 bath vacation home with an awesome outdoor lounge area! This ranch style home ...

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    Details
  • The Seagrape Villa - Luxury Accommodation in Paradise
    From $733 per night (USD)

    Expedia

    The Seagrape Villa - Luxury Accommodation in Paradise

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Siesta Key Home Minutes to the Beach! The Seagrape Villa provides a luxurious 10 person retreat with an abundance of am ...

    From $733 per night (USD)

    Expedia

    Details
  • Family Vacation Home with Pool and Spa, 2-min walk to Beach - Stone's Throw
    From $432 per night (USD)

    VRBO

    Family Vacation Home with Pool and Spa, 2-min walk to Beach - Stone's Throw

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Stone’s Throw by Lido Key Vacations Home in Lido Key, FL 34236 #VR22-00037 Minimum stay duration of 7 days/nights W ...

    From $432 per night (USD)

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  • Lido Lux Beach House
    From $552 per night (USD)

    Expedia

    Lido Lux Beach House

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Just steps from the beach walk to everything, restaurants, and shopping! Enjoy the rooftop sun deck with a peek-a -boo v ...

    From $552 per night (USD)

    Expedia

    Details
  • Bright Sarasota Bungalow - 5 Mi to Siesta Beach!
    From $168 per night (USD)

    VRBO

    Bright Sarasota Bungalow - 5 Mi to Siesta Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Looking for a tropical escape? This cozy cottage is perfect for you! A short drive or bike ride will be all that separat ...

    From $168 per night (USD)

    VRBO

    Details
  • GULF OF MEXICO & SARASOTA BAY VIEWS!  SUNRISE TO SUNSET at L'ELEGANCE LIDO KEY!
    From $416 per night (USD)

    Expedia

    GULF OF MEXICO & SARASOTA BAY VIEWS! SUNRISE TO SUNSET at L'ELEGANCE LIDO KEY!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    A tropical beach paradise fourth floor condominium right on Lido Beach. The unique "through & through" floor plan of th ...

    From $416 per night (USD)

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    Details
  • Newly remodeled close to downtown and beaches 3/2 heated pool and screened lanai
    From $403 per night (USD)

    VRBO

    Newly remodeled close to downtown and beaches 3/2 heated pool and screened lanai

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Great location! In the desirable Southgate neighborhood on a quiet street close to everything Sarasota has to offer! Com ...

    From $403 per night (USD)

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    Details
  • Cozy house near Siesta Key Beach
    From $193 per night (USD)

    Expedia

    Cozy house near Siesta Key Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our newly furnished home. When you walk up to it, it looks like a cozy cottage too. The inside is fresh new a ...

    From $193 per night (USD)

    Expedia

    Details
  • Private Heated Pool, walk to St Armand's! Perfect for families!
    From $742 per night (USD)

    VRBO

    Private Heated Pool, walk to St Armand's! Perfect for families!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    301 Jackson Dr Sarasota FL 34236 Vacation Rental License #VR22-00132 Minimum stay duration of 7 days/nights Welcome to ...

    From $742 per night (USD)

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  • Siesta Key Waterfront Estate heated Pool Privacy!
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    Siesta Key Waterfront Estate heated Pool Privacy!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    14

    This wooded property is unreal and our 5 star ratings agree! 1 acre on the water for your entire family or group to rela ...

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    Details
  • 4 bedroom 4 bathroom waterfront home on luxurious Bird Key, Sarasota
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    4 bedroom 4 bathroom waterfront home on luxurious Bird Key, Sarasota

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    6

    This beautiful home has 4 bedrooms with en suite bathrooms perfectly set up for a family. Large living room dining room ...

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    Details
  • 🏝Perfectly Located Between St. Armands Circle & Lido Beach + Heated Pool/Spa
    From $712 per night (USD)

    Expedia

    🏝Perfectly Located Between St. Armands Circle & Lido Beach + Heated Pool/Spa

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to “Lido Sands”… a cozy 4 bedroom 3 bath vacation home with a great private heated pool and spa and awesome loun ...

    From $712 per night (USD)

    Expedia

    Details
  • 'The Melrose Sarasota' w/ Large Private Lanai
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    'The Melrose Sarasota' w/ Large Private Lanai

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Your perfect Florida vacation is waiting for you at this well-appointed 4-bedroom, 3-bathroom home in Sarasota. Start yo ...

    Click For Pricing

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    Details
  • Brand New Beautiful Rental Close to Beaches!!!!
    From $258 per night (USD)

    Expedia

    Brand New Beautiful Rental Close to Beaches!!!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Family friendly vacation rental located only 15 minutes from beautiful Siesta Key beach and downtown Sarasota. It is lo ...

    From $258 per night (USD)

    Expedia

    Details