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Results: 691 Rentals

  • The Forever Beach Cottage Studio Room!
    From $85 per night (USD)

    VRBO

    The Forever Beach Cottage Studio Room!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    We have designed this studio to make you feel at home, while giving you the coastal feel of Sarasota so you can feel lik ...

    From $85 per night (USD)

    VRBO

    Details
  • \Safe & Clean\ 3.5 miles to Siesta Key, Lovely 3 bedr Home for the Entire Family
    From $311 per night (USD)

    Expedia

    \"Safe & Clean\" 3.5 miles to Siesta Key, Lovely 3 bedr Home for the Entire Family

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    New listing: Dawson House is closely located within a few miles to Siesta Key and close to downtown Sarasota. This home ...

    From $311 per night (USD)

    Expedia

    Details
  • Starfish Bungalow Private Entrance and Kitchenette
    From $115 per night (USD)

    VRBO

    Starfish Bungalow Private Entrance and Kitchenette

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Remodeled, beach-themed, spacious bedroom/living room/bath with private entrance. Comfortable king bed, sofa sleeper and ...

    From $115 per night (USD)

    VRBO

    Details
  • Sarasota creekside pool home oasis, close to beaches and activities.
    From $350 per night (USD)

    Expedia

    Sarasota creekside pool home oasis, close to beaches and activities.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Sarasota Florida. A premier: vacation, adventure, retirement destination. Located on the best (West) coast of ...

    From $350 per night (USD)

    Expedia

    Details
  • Downtown Sarasota Home By Siesta Key and Golfing
    From $75 per night (USD)

    VRBO

    Downtown Sarasota Home By Siesta Key and Golfing

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Beautiful remodeled apartment in a quiet neighborhood. 10min to Dwtn, 15min to Siesta & Lido Beach. Unit has 1 bedroom w ...

    From $75 per night (USD)

    VRBO

    Details
  • Heated Pool ❤ Home- Close to Beaches, Restaurants
    From $247 per night (USD)

    Expedia

    Heated Pool ❤ Home- Close to Beaches, Restaurants

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $247 per night (USD)

    Expedia

    Details
  • Sparkling Rental Close to Beaches and Downtown
    From $285 per night (USD)

    VRBO

    Sparkling Rental Close to Beaches and Downtown

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This charming home has sparkling restored Terrazzo floors that lend a beautiful shine throughout this 3 bed/ 2 bath beac ...

    From $285 per night (USD)

    VRBO

    Details
  • Fairy-Tale Getaway Private Entry Near Siesta Key
    From $82 per night (USD)

    Expedia

    Fairy-Tale Getaway Private Entry Near Siesta Key

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    About this space: Newly remodeled, spacious bedroom/bath with a private entrance. Luxuriate in a comfortable queen bed, ...

    From $82 per night (USD)

    Expedia

    Details
  • Pool ❤ Home - Close to Beaches, Food, Downtown, Parks, St. Armand's, etc
    From $250 per night (USD)

    VRBO

    Pool ❤ Home - Close to Beaches, Food, Downtown, Parks, St. Armand's, etc

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

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

    From $250 per night (USD)

    VRBO

    Details
  • Get To the Beach!  Only 5 miles to Siesta Key Beach!
    From $115 per night (USD)

    Expedia

    Get To the Beach! Only 5 miles to Siesta Key Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Charming updated duplex villa where you can enjoy beaches, shopping, restaurants and downtown Sarasota nightlife! Recen ...

    From $115 per night (USD)

    Expedia

    Details
  • Sarasota House w\/ Private Pool - 4 Mi to Beach!
    From $188 per night (USD)

    VRBO

    Sarasota House w\/ Private Pool - 4 Mi to Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Whether you're looking to spend time by the pool or at the beach, 'Siesta Jewel’ is perfect for travelers on a memorable ...

    From $188 per night (USD)

    VRBO

    Details
  • Near Siesta Key - single story pet friendly
    From $131 per night (USD)

    Expedia

    Near Siesta Key - single story pet friendly

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Newly renovated home in Sarasota. All new ceramic floors with new kitchen including granite counter tops, dishwasher, mi ...

    From $131 per night (USD)

    Expedia

    Details
  • Beautiful, Spacious Family Friendly Vacation Home
    From $299 per night (USD)

    VRBO

    Beautiful, Spacious Family Friendly Vacation Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Book your next vacation at this lovely home, and you won't be disappointed! Brand new furniture throughout the entire ho ...

    From $299 per night (USD)

    VRBO

    Details
  • Family Retreat with Pool, Games, Dock, Fishing, Golf by RedAwning
    From $221 per night (USD)

    Expedia

    Family Retreat with Pool, Games, Dock, Fishing, Golf by RedAwning

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Tanglewood is a relaxing vacation spot for outdoors fun and adventure--offering fishing, kayaking, swimming, bird-watchi ...

    From $221 per night (USD)

    Expedia

    Details
  • Pinecraft Sunset Tiny Home
    From $146 per night (USD)

    VRBO

    Pinecraft Sunset Tiny Home

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: This unique comfortable tiny home in the heart of Sarasota. Close to Pinecraft, beaches, shops and restaurants. ...

    From $146 per night (USD)

    VRBO

    Details
  • The Cozy Beach Suite of Sunny Sarasota!
    From $83 per night (USD)

    Expedia

    The Cozy Beach Suite of Sunny Sarasota!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Beautifully designed studio inspired guest suite in the heart of Sarasota ready for your next stay! We designed this sui ...

    From $83 per night (USD)

    Expedia

    Details
  • Priced Right Near Arlington Park Outdoor Kitchen
    From $223 per night (USD)

    VRBO

    Priced Right Near Arlington Park Outdoor Kitchen

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Ready for a relaxing, worry-free Florida vacation!? Priced right is a fabulous saltwater, contemporary pool home locate ...

    From $223 per night (USD)

    VRBO

    Details
  • \Safe & Clean\  Ultra Convenient Location \/  3 Bed \/ 2 baths  updated pool home
    From $319 per night (USD)

    Expedia

    \"Safe & Clean\" Ultra Convenient Location \/ 3 Bed \/ 2 baths updated pool home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This beautiful and completely updated 3 bedroom / 2 baths single family pool home is located 1 mile to Siesta Key North ...

    From $319 per night (USD)

    Expedia

    Details
  • Bright, cozy studio in the middle of Sarasota
    From $97 per night (USD)

    VRBO

    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 $97 per night (USD)

    VRBO

    Details
  • Large and bright studio in the middle of Sarasota
    From $75 per night (USD)

    Expedia

    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 $75 per night (USD)

    Expedia

    Details
  • Newly remodeled close to downtown and beaches 3\/2 heated pool and screened lanai
    From $400 per night (USD)

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    NEW TO VRBO -Great location! Close to everything Sarasota has to offer! Completely remodeled, open concept 3 bed 2 bath ...

    From $400 per night (USD)

    VRBO

    Details
  • Casa Lemon
    From $115 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 $115 per night (USD)

    Expedia

    Details
  • Recently Updated Apartment close to Siesta Key
    From $95 per night (USD)

    VRBO

    Recently Updated Apartment close to Siesta Key

    Bedrooms:
    2
    Bathrooms:
    2
    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 $95 per night (USD)

    VRBO

    Details
  • Newly renovated - sleeps 10 & pet friendly
    From $121 per night (USD)

    Expedia

    Newly renovated - sleeps 10 & pet friendly

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Newly renovated house- 10 minutes to Siesta Key You cannot get a better location. This the perfect place to be your ho ...

    From $121 per night (USD)

    Expedia

    Details
  • 2 Bedroom Single_family 427467 by Houzlet
    Click For Pricing

    Expedia

    2 Bedroom Single_family 427467 by Houzlet

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Seasonal/ Short-Term/Monthly Rental. South Gate charmer ready for seasonal or short term guests! Fully Furnished Pool Ho ...

    Click For Pricing

    Expedia

    Details
  • 2 Bedroom Single_family 95132 by Houzlet
    Click For Pricing

    Expedia

    2 Bedroom Single_family 95132 by Houzlet

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    MOVE IN and Relax in this charming Home- two bedrooms + a den, two bath, FURNISHED. Centrally located minutes from DOWNT ...

    Click For Pricing

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    Details
  • Beach Bum Bungalow-Sarasota-10 min to Siesta Key
    From $147 per night (USD)

    VRBO

    Beach Bum Bungalow-Sarasota-10 min 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 $147 per night (USD)

    VRBO

    Details
  • Sunseeker Bungalow-Sarasota-10 min to Siesta Key
    From $148 per night (USD)

    Expedia

    Sunseeker Bungalow-Sarasota-10 min to Siesta Key

    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 $148 per night (USD)

    Expedia

    Details
  • Comfortable home in charming Southgate
    From $160 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 $160 per night (USD)

    VRBO

    Details
  • Quiet family home located centrally to beaches and downtown Sarasota
    From $114 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 $114 per night (USD)

    Expedia

    Details
  • 4 Bedroom Pool House in Heart of Sarasota
    From $212 per night (USD)

    VRBO

    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 ...

    From $212 per night (USD)

    VRBO

    Details
  • Sunrise Tiny Home - New&Cozy
    From $162 per night (USD)

    Expedia

    Sunrise Tiny Home - New&Cozy

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Located in the heart of Sarasota, the Sunrise tiny home offers large living and is anything but ordinary. One b ...

    From $162 per night (USD)

    Expedia

    Details
  • Sunshine Tiny Home, Pinecraft
    From $162 per night (USD)

    VRBO

    Sunshine Tiny Home, Pinecraft

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Located in the heart of Sarasota, the Sunshine tiny home offers large living and is anything but ordinary. One ...

    From $162 per night (USD)

    VRBO

    Details
  • Key Lime Tiny Home, New&Cozy
    From $162 per night (USD)

    Expedia

    Key Lime Tiny Home, New&Cozy

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Located in the heart of Sarasota, the Key Lime tiny home offers large living and is anything but ordinary. One ...

    From $162 per night (USD)

    Expedia

    Details
  • Pinecraft Cottage Tiny Home
    From $125 per night (USD)

    VRBO

    Pinecraft Cottage Tiny Home

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Comfortable cottage in the heart of Sarasota. Close to Pinecraft, beaches, shops and restaurants. Great for a ...

    From $125 per night (USD)

    VRBO

    Details
  • Hummingbird House, New & Cozy
    From $162 per night (USD)

    Expedia

    Hummingbird House, New & Cozy

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Located in the heart of Sarasota, the memorable Hummingbird tiny home is anything but ordinary. One bedroom wit ...

    From $162 per night (USD)

    Expedia

    Details
  • Pinecraft Tiny Home 2
    From $146 per night (USD)

    VRBO

    Pinecraft Tiny Home 2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Comfortable tiny home in the heart of Sarasota. Close to Pinecraft, beaches, shops and restaurants. Great for ...

    From $146 per night (USD)

    VRBO

    Details
  • Contemporary Ranch, near Siesta Key & Donwtown SRQ
    From $280 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 $280 per night (USD)

    Expedia

    Details
  • Sun Tans & Fairways: Heated Pool and Hot Tub
    From $399 per night (USD)

    VRBO

    Sun Tans & Fairways: Heated Pool and Hot Tub

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    The whole group will enjoy easy access to everything from this centrally located place. Sun Tans & Fairways is a home th ...

    From $399 per night (USD)

    VRBO

    Details
  • Siesta Side Stay
    From $175 per night (USD)

    VRBO

    Siesta Side Stay

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located approximately 5 miles from Siesta Key beach & Siesta Key Village and 2.5 miles from downtown Sarasota & the mari ...

    From $175 per night (USD)

    VRBO

    Details
  • Southgate: Lovely remodeled 3 bedroom pool villa 2.5 Miles from Siesta Key
    From $203 per night (USD)

    VRBO

    Southgate: Lovely remodeled 3 bedroom pool villa 2.5 Miles from Siesta Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to this one-of-a-kind 3-bedroom, 2-bathroom home with an extra-large pool in the heart of Sarasota. This house ...

    From $203 per night (USD)

    VRBO

    Details
  • Well appointed three bedroom two bath home with heated pool.
    From $175 per night (USD)

    VRBO

    Well appointed three bedroom two bath home with heated pool.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Three bedroom two bath home in a gulf community. Terrazzo floors throughout the entire home. Private master suite with ...

    From $175 per night (USD)

    VRBO

    Details
  • Beautiful Beach Cottage 2 Bed\/2 Bath 10 Minutes To Siesta Key Beach and Downtown
    From $197 per night (USD)

    VRBO

    Beautiful Beach Cottage 2 Bed\/2 Bath 10 Minutes To Siesta Key Beach and Downtown

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This totally renovated adorable beach cottage is located less than a 10 minute drive to Siesta Key. Siesta Key is a beac ...

    From $197 per night (USD)

    VRBO

    Details
  •  Immaculate, 3 bedroom, 2 bath Close to Siesta Beach, with HEATED POOL
    From $179 per night (USD)

    VRBO

    Immaculate, 3 bedroom, 2 bath Close to Siesta Beach, with HEATED POOL

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Lovely single story home built in 1962, remodeled completely 2014. As the photos show, the bedrooms are spacious with th ...

    From $179 per night (USD)

    VRBO

    Details
  • Close to Beach & Downtown w\/Pool, Family Friendly
    From $281 per night (USD)

    VRBO

    Close to Beach & Downtown w\/Pool, Family Friendly

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Relax & unwind in our newly updated single level 3 bedroom, 2 bath, 2 car garage with private pool. Located in Southgate ...

    From $281 per night (USD)

    VRBO

    Details
  • Mid-Century Bungalow By Arlington Park in South Gate, Central to Siesta and Lido
    From $197 per night (USD)

    VRBO

    Mid-Century Bungalow By Arlington Park in South Gate, Central to Siesta and Lido

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    A newly updated jewel in the heart of Sarasota's historic South Gate neighborhood, this newly renovated, bright home sta ...

    From $197 per night (USD)

    VRBO

    Details
  • Private single family home in great location. Close to downtown and beaches.
    From $190 per night (USD)

    VRBO

    Private single family home in great location. Close to downtown and beaches.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This is an updated 2 Bed/2 bath clean home in great neighborhood. It has everything you need including all kitchen items ...

    From $190 per night (USD)

    VRBO

    Details
  • Newly furnished and re-modeled house close to Gulf beaches and downtown Sarasota
    From $200 per night (USD)

    VRBO

    Newly furnished and re-modeled house close to Gulf beaches and downtown Sarasota

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    Spacious home with more than 1500 sq. ft. of living space for all your flexcation needs of relaxation, work remote and / ...

    From $200 per night (USD)

    VRBO

    Details
  • Family-Friendly Oasis - Salt Water Pool - Minutes From Beaches & Entertainment
    From $199 per night (USD)

    VRBO

    Family-Friendly Oasis - Salt Water Pool - Minutes From Beaches & Entertainment

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    As of January 2023 our pool has been converted to a salt water system instead of chlorine. Better for your skin, better ...

    From $199 per night (USD)

    VRBO

    Details
  • Sarasota Waterfront Paradise- Location, Location...!!\n
    From $270 per night (USD)

    Expedia

    Sarasota Waterfront Paradise- Location, Location...!!\n

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our exquisite waterfront retreat in the heart of Sarasota! This fully-stocked private home is a true gem, boa ...

    From $270 per night (USD)

    Expedia

    Details
  • Gorgeous renovation with pool, minutes from beach
    From $175 per night (USD)

    VRBO

    Gorgeous renovation with pool, minutes from beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Light, bright and newly renovated. Beautifully decorated 3 bedroom home minutes from Siesta Key and downtown. The spacio ...

    From $175 per night (USD)

    VRBO

    Details
  • Coastal Charm: 1\/1 Studio in City - 10 mins to Downtown! 15 mins to Lido Beach
    From $99 per night (USD)

    Expedia

    Coastal Charm: 1\/1 Studio in City - 10 mins to Downtown! 15 mins to Lido Beach

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    3

    Relaxing, peaceful space that's perfect for working business professionals, small families with children, and couples lo ...

    From $99 per night (USD)

    Expedia

    Details
  • Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
    From $170 per night (USD)

    VRBO

    Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Relaxing beach vibe, 2.6mi from Siesta Beach and 2.5mi from beautiful downtown Sarasota Com enjoy this private small r ...

    From $170 per night (USD)

    VRBO

    Details
  • 3817-3819 Villa Franca · 6 beds, 2 kitchens, laundry near the beach
    From $231 per night (USD)

    Expedia

    3817-3819 Villa Franca · 6 beds, 2 kitchens, laundry near the beach

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Welcome to our mid-century modern house, just minutes away from the stunning Siesta Key Beach! This beautifully designed ...

    From $231 per night (USD)

    Expedia

    Details
  • Casa de Siesta Home in Sarasota by RVA
    From $220 per night (USD)

    VRBO

    Casa de Siesta Home in Sarasota by RVA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This classic Southgate Sarasota 3BR/2BA Remodeled Home sleeps 6, features a refreshing pool, and is conveniently located ...

    From $220 per night (USD)

    VRBO

    Details
  • Fully Renovated Mid Century Ranch minutes from Siesta Key and Downtown Sarasota!
    From $228 per night (USD)

    Expedia

    Fully Renovated Mid Century Ranch minutes from Siesta Key and Downtown Sarasota!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Completely renovated. Huge open floorplan perfect for entertaining with a chefs kitchen. Privacy fenced back yard comple ...

    From $228 per night (USD)

    Expedia

    Details
  • Coastal Comfort Getaway in the Heart of SRQ
    From $300 per night (USD)

    VRBO

    Coastal Comfort Getaway in the Heart of SRQ

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Coastal Comfort Getaway! Discover the charm of this thoughtfully designed 3/2 heated pool home that embodies ...

    From $300 per night (USD)

    VRBO

    Details
  • Phillip Creek House with Kayaks
    From $275 per night (USD)

    Expedia

    Phillip Creek House with Kayaks

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This beauty is located on a gorgeous section of Philippi Creek with a shore filled with magnificent stands of mangrove, ...

    From $275 per night (USD)

    Expedia

    Details
  • New Rental Sleek Modern Private Home, WiFi, Lanai
    From $250 per night (USD)

    VRBO

    New Rental Sleek Modern Private Home, WiFi, Lanai

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Sarasota & famous Siesta Key, renowned for its stunning sunsets and powdery white sands. It's no wonder it's ...

    From $250 per night (USD)

    VRBO

    Details
  • Lovely New Pinecraft Suite
    From $95 per night (USD)

    Expedia

    Lovely New Pinecraft Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy a brand new apartment experience central to Sarasota's best attractions. Come appreciate the beautiful city of Sar ...

    From $95 per night (USD)

    Expedia

    Details
  • Lovely New Pinecraft Cottage
    From $146 per night (USD)

    VRBO

    Lovely New Pinecraft Cottage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy a brand new cottage experience central to Sarasota's best attractions. Come appreciate the beautiful city of Saras ...

    From $146 per night (USD)

    VRBO

    Details
  • Lovely New Pinecraft Home
    From $308 per night (USD)

    Expedia

    Lovely New Pinecraft Home

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Enjoy a brand new vacation home experience central to Sarasota's best attractions. Come appreciate the beautiful city of ...

    From $308 per night (USD)

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  • Comfy studio in Sarasota
    From $68 per night (USD)

    VRBO

    Comfy studio in Sarasota

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Studio located in multi family house with nice & quiet tenants in nice neighborhoods .The Centrally located, 5 minutes f ...

    From $68 per night (USD)

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  • Spacious studio with garage
    From $75 per night (USD)

    Expedia

    Spacious studio with garage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The studio is in a central and convenient location. Five minutes drive to Sarasota memorial hospital, 10 minutes to Sies ...

    From $75 per night (USD)

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  • Adorable Beach Bungalow with privacy yet 10 minutes to many events
    From $165 per night (USD)

    VRBO

    Adorable Beach Bungalow with privacy yet 10 minutes to many events

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This cute-as-a-button 2 bedroom bungalow located in the coveted and charming Southgate neighborhood, centrally located i ...

    From $165 per night (USD)

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    Details
  • Adorable house with private pool- 15min from the Beach!
    From $286 per night (USD)

    Expedia

    Adorable house with private pool- 15min from the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to this classic Southgate Sarasota 3BR/2BA Remodeled Home, which features a refreshing pool, and is conveniently ...

    From $286 per night (USD)

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    Details
  • Private Retreat on Siesta Dr with stunning pool
    From $406 per night (USD)

    VRBO

    Private Retreat on Siesta Dr with stunning pool

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to our luxurious 4 bedroom, 3.5 bath home with a private heated pool & outdoor bar area! Perfectly located just ...

    From $406 per night (USD)

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  • Fenced Backyard with Hot Tub!
    From $100 per night (USD)

    VRBO

    Fenced Backyard with Hot Tub!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Private home, 3 bedroom 2 full baths. Suitable for 8 guests comfortably. Two bedrooms with Kings beds, third bedroom wit ...

    From $100 per night (USD)

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    Details
  • Barefoot Bungalow -Private Heated Pool Home\/minutes from Siesta Key Beach
    From $296 per night (USD)

    VRBO

    Barefoot Bungalow -Private Heated Pool Home\/minutes from Siesta Key Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Three Bedroom- Two Full Bath- sleeps 8. Private pool home. Kick your shoes off, relax, and enjoy this peaceful centrall ...

    From $296 per night (USD)

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    Details
  • Bright and Open Designer Pool Home near Siesta Key
    From $282 per night (USD)

    Expedia

    Bright and Open Designer Pool Home near Siesta Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This fabulously updated pool home is just 3 miles from Siesta Key & features a bright open floor plan, 3 separate bedroo ...

    From $282 per night (USD)

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    Details
  • Inviting dog-friendly home with yard, firepit, central AC, & W\/D
    From $157 per night (USD)

    VRBO

    Inviting dog-friendly home with yard, firepit, central AC, & W\/D

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    The Tuttle House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...

    From $157 per night (USD)

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  • Slice of Paradise - Pool house close to Siesta Key
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    VRBO

    Slice of Paradise - Pool house close to Siesta Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautifully updated Southgate pool house close to Siesta Key and Downtown Get your beach house vacation and private Sanc ...

    Click For Pricing

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    Details
  • 1 Bedroom  631561 by Houzlet
    Click For Pricing

    Expedia

    1 Bedroom 631561 by Houzlet

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience the Essence Indulge in the essence of a Mid-Century Modern paradise, just minutes away from the renowned Sies ...

    Click For Pricing

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    Details
  • Pinecraft 1Br\/1B -  Watch the Park, Walk to Restaurants, 15 Min drive to beaches
    From $115 per night (USD)

    Expedia

    Pinecraft 1Br\/1B - Watch the Park, Walk to Restaurants, 15 Min drive to beaches

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Two nights, two weeks or two months - this is the perfect getaway in the middle of Sarasota. Elegant and cozy 1 bedroom ...

    From $115 per night (USD)

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    Details
  • Private Pool, Sunnyside
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    Private Pool, Sunnyside

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Sunnyside! This charming 3-bedroom, 2-bath, single-level private pool home is located in a lovely neighborhoo ...

    Click For Pricing

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    Details
  • BBQ, King bed, fenced yard near Siesta Key Beach
    From $79 per night (USD)

    Expedia

    BBQ, King bed, fenced yard near Siesta Key Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Cute beach themed house 3 miles from Siesta Key beach and minutes from Main Street down town Sarasota. The house is in ...

    From $79 per night (USD)

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    Details
  • Beautiful and Renovated Sarasota Home with Pool
    From $159 per night (USD)

    VRBO

    Beautiful and Renovated Sarasota Home with Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy a luxurious stay in this stunning 3-bedroom, 2-bathroom home nestled in the midst of natural beauty. With a gorgeo ...

    From $159 per night (USD)

    VRBO

    Details
  • 5 min from Sarasota downtown. Cozy 3\/2 with heated pool
    From $250 per night (USD)

    Expedia

    5 min from Sarasota downtown. Cozy 3\/2 with heated pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Just a few minutes from the downtown and Siesta Key Beach (number one in USA). 3 bedroom 2 bathrom home with heated pool ...

    From $250 per night (USD)

    Expedia

    Details
  • Slice of paradise II - Pool house close to SK
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    VRBO

    Slice of paradise II - Pool house close to SK

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to our Sarasota Beach house. We lived in the house for 4 years and converted it into a vacation rental a year ag ...

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    Details
  • Slice of Paradise - Pool house close to Siesta Key
    Click For Pricing

    Expedia

    Slice of Paradise - Pool house close to Siesta Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Beautifully updated Southgate pool house close to Siesta Key and Downtown Get your beach house vacation and private Sanc ...

    Click For Pricing

    Expedia

    Details
  • SunDaze Cottage - Heated Pool - King Bed
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    Expedia

    SunDaze Cottage - Heated Pool - King Bed

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Escape to tranquility in this peaceful haven. Embrace your home away from home, bask by the pool, sizzle steaks on the g ...

    Click For Pricing

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    Details
  • The Clematis - Entire house
    From $165 per night (USD)

    Expedia

    The Clematis - Entire house

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Clematis sits in the charming and historic Arlington Park neighborhood on a tree-lined street with majestic oak tree ...

    From $165 per night (USD)

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  • The Sweet Spot in Sarasota
    From $276 per night (USD)

    VRBO

    The Sweet Spot in Sarasota

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to the “Sweet Spot” in Sarasota! This spacious, charming retro designer home is the perfect reprieve in a quiet ...

    From $276 per night (USD)

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  • Centrally located <10 min to beach 2 bd 1 ba Home!
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    Expedia

    Centrally located <10 min to beach 2 bd 1 ba Home!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Remodeled Centrally located home! It has everything you will need to enjoy your time in Sarasota! * Less than 1 mile to ...

    Click For Pricing

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  • Coastal Sarasota Pool Home near Siesta Key Beach
    From $300 per night (USD)

    VRBO

    Coastal Sarasota Pool Home near Siesta Key Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    *NEW* This home is situated in central Sarasota in the highly desired neighborhood of South Gate. This spacious & though ...

    From $300 per night (USD)

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  • Beautiful home with hot tub 4 miles from Siesta Key Bridge!
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    Expedia

    Beautiful home with hot tub 4 miles from Siesta Key Bridge!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Beautiful three-bedroom home 4 miles from Siesta Key Bridge! Comfortably sleeps 8 guests. Relax in the hot tub in the pr ...

    Click For Pricing

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    Details
  • NEW LISTING!!!! Casa Verde Sarasota Retreat-Inside is gorgeous too!
    From $250 per night (USD)

    VRBO

    NEW LISTING!!!! Casa Verde Sarasota Retreat-Inside is gorgeous too!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    ❤Welcome to paradise! Safe, extra clean, brand new everything...wonderful neighborhood ! Your private heated pool and l ...

    From $250 per night (USD)

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    Details
  • 5 minutes from Lido Keys 7 min to Siesta Keys
    From $170 per night (USD)

    Expedia

    5 minutes from Lido Keys 7 min to Siesta Keys

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Only 7 minutes from Siesta Keys 7 minutes from the St Armands Circle 5 minutes from Lido Keys situated on a central loc ...

    From $170 per night (USD)

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    Details
  • Classic Florida escape with pool and beautiful yard to bask in, close to beach!
    From $209 per night (USD)

    VRBO

    Classic Florida escape with pool and beautiful yard to bask in, close to beach!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your next vacation home away from home. This beautiful 3 bedroom, 3 bath ranch has everything you need. Out ...

    From $209 per night (USD)

    VRBO

    Details
  • Near Siesta Key Beach, this Boho chic Sarasota pool home will feel like an oasis
    From $228 per night (USD)

    Expedia

    Near Siesta Key Beach, this Boho chic Sarasota pool home will feel like an oasis

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your Bohemian chic pet-friendly holiday home away from home. This 2-bed, plus 3rd bed sunroom/flex space {wit ...

    From $228 per night (USD)

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  • Get away from the noise of life.
    From $320 per night (USD)

    VRBO

    Get away from the noise of life.

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Do you want a break from life? Come stay at our Phillippi Creek Retreat! Newly furnished 2 bedroom, 3 bathroom pool hom ...

    From $320 per night (USD)

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    Details
  • Coconut Palm-Luxury Suite-5 miles to Siesta Key!
    From $78 per night (USD)

    Expedia

    Coconut Palm-Luxury Suite-5 miles to Siesta Key!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to your perfect getaway destination – The Coconut Palm! Meticulously remodeled and tastefully decorated with you ...

    From $78 per night (USD)

    Expedia

    Details
  • SARASOTA Heated Pool - Pet Friendly - Garage w\/ EV Charger - Close to Beaches!
    From $219 per night (USD)

    VRBO

    SARASOTA Heated Pool - Pet Friendly - Garage w\/ EV Charger - Close to Beaches!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to this recently renovated mid-century modern house in Sarasota which is in very close proximity to all the best ...

    From $219 per night (USD)

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  • Siesta Key Beach 10 minutes away!
    From $230 per night (USD)

    VRBO

    Siesta Key Beach 10 minutes away!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    This property is on a quiet street. Perfectly situated for evening strolls after your day at the near by siesta key beac ...

    From $230 per night (USD)

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    Details
  • Spacious 3\/3 Apt w\/Hot Tub\/75in TV\/Mac Computer
    From $134 per night (USD)

    VRBO

    Spacious 3\/3 Apt w\/Hot Tub\/75in TV\/Mac Computer

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to your dream retreat! This beautifully adorned 3-bedroom rental unit is the epitome of comfort and style. Need ...

    From $134 per night (USD)

    VRBO

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  • First Class near Beach Downtown and 2 Hospitals
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    Expedia

    First Class near Beach Downtown and 2 Hospitals

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Quiet neighborhood close to two golf courses (The Palms and Village Green), centrally located to beaches, downtown and e ...

    Click For Pricing

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  • Luxury home\/heated private pool mins drive to Siesta Key & Downtown Sarasota.
    From $468 per night (USD)

    VRBO

    Luxury home\/heated private pool mins drive to Siesta Key & Downtown Sarasota.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Luxury ranch home, private pool and veranda, only a short drive to Siesta Key Beach, the #1 beach in the United States. ...

    From $468 per night (USD)

    VRBO

    Details
  • The Pink Flamingo Private Pool Paradise - 7 min to Siesta Key
    From $358 per night (USD)

    Expedia

    The Pink Flamingo Private Pool Paradise - 7 min to Siesta Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Amazing New HEATED SALT WATER POOL! THE PINK FlAMINGO is our Newest addition Vacation Home! MidCentury Modern Dream N ...

    From $358 per night (USD)

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  • Elegant Siesta Getaway
    From $190 per night (USD)

    VRBO

    Elegant Siesta Getaway

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    A home with a unique style of its own. This charming 3 bedroom house will be able to satisfy all your needs while stayin ...

    From $190 per night (USD)

    VRBO

    Details
  • 3\/2 stunner w\/ heated pool & hot tub paradise, minutes to beaches, NO FEES!
    From $257 per night (USD)

    Expedia

    3\/2 stunner w\/ heated pool & hot tub paradise, minutes to beaches, NO FEES!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy our oasis from the world as we share this awesome updated 1950s pool home that's 4 miles from the beaches of Siest ...

    From $257 per night (USD)

    Expedia

    Details