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  • 210 CS Tower 2BR 2BA Sleeps 6
    From $257 per night (USD)

    VRBO

    210 CS Tower 2BR 2BA Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...

    From $257 per night (USD)

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    Details
  • 2/2 (035) Tower Partial North View NE
    From $260 per night (USD)

    VRBO

    2/2 (035) Tower Partial North View NE

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 35- 2 Bedroom and 2 Bathroom Condominium in the Tower | View of the neighboring sea grapes | Voted America's #1 B ...

    From $260 per night (USD)

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    Details
  • Garden Terrace
    From $1400 per night (USD)

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    Garden Terrace

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    SHORT WALK TO FAMOUS SIESTA WHITE SAND BEACH & QUAINT ISLAND VILLAGE. Situated in the quiet and welcoming neighborhood ...

    From $1400 per night (USD)

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  • Beautiful Spacious Pool Home -access to several beaches
    From $125 per night (USD)

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    Beautiful Spacious Pool Home -access to several beaches

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This open and spacious three bedroom pool home has been remodeled and awaits your arrival. From the moment you enter the ...

    From $125 per night (USD)

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    Details
  • Heritage Oaks Golf Condo
    From $150 per night (USD)

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    Heritage Oaks Golf Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Lovely 2 bedroom, 2 bath condominium in gated Heritage Oaks Golf & Country Club located just 15 minutes from the beautif ...

    From $150 per night (USD)

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    Details
  • Beach Harbor Club
    From $150 per night (USD)

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    Beach Harbor Club

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Penthouse unit with view of Gulf from all rooms.2 Rooftop patios with furnishings. Private beach across the Drive and p ...

    From $150 per night (USD)

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    Details
  • Lido Key - Great price + breakfast!
    From $75 per night (USD)

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    Lido Key - Great price + breakfast!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This ideally positioned 1 bedrm. island condo is occasionally available while the owner/resident is away during "season" ...

    From $75 per night (USD)

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    Details
  • Vista Hermosa Cabana
    From $125 per night (USD)

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    Vista Hermosa Cabana

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Park the car, you will not get back in it til you leave, if you do leave at all. Welcome to the south end of Siesta Key ...

    From $125 per night (USD)

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  • Seagate House
    From $79 per night (USD)

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    Seagate House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The newly renovated open floor-plan in this 2,500 sq. foot home offers new amenities throughout, designer colors, design ...

    From $79 per night (USD)

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  • 2/2 (065) Tower Partial North View Ne
    From $260 per night (USD)

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    2/2 (065) Tower Partial North View Ne

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 65- 2 Bedroom and 2 Bathroom Condominium with Partial North Views. | This two bedroom, two-bath condo is located o ...

    From $260 per night (USD)

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    Details
  • Condo @ Our House At the Beach
    From $134 per night (USD)

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    Condo @ Our House At the Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    “Pristine sand, blue skies - 'Number 1 Beach'” The Best Thing to look forward to after a Day on the Beach Is... ...Ano ...

    From $134 per night (USD)

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    Details
  • 1/1 (106) Tower East View
    From $150 per night (USD)

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    1/1 (106) Tower East View

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unit 106 - 1 Bedroom 1 Bathroom Condominium East View | | Nestled between the Gulf of Mexico and Sarasota Bay, this pri ...

    From $150 per night (USD)

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    Details
  • Chateau Village 103
    From $75 per night (USD)

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    Chateau Village 103

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $75 per night (USD)

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  • Relaxing Siesta Key Condo
    From $100 per night (USD)

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    Relaxing Siesta Key Condo

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    4

    Come and enjoy the island lifestyle on Siesta Key in this lovely furnished 3rd floor condo. Enjoy your morning coffee or ...

    From $100 per night (USD)

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    Details
  • Florida Sarasota Siesta Beach
    From $184 per night (USD)

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    Florida Sarasota Siesta Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Rarely rentable Gulf Gate home with 2 bedrooms and 2 bathrooms. Completely redone inside. Incredible kitchen with design ...

    From $184 per night (USD)

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    Details
  • SARASOTA SURF AND RACQUET Y101
    From $145 per night (USD)

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    SARASOTA SURF AND RACQUET Y101

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This exceptional GROUND FLOOR condo Y101, is one of the most desirable condos in this complex and on Crescent Beach. The ...

    From $145 per night (USD)

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    Details
  • BS 1269
    From $150 per night (USD)

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    BS 1269

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Deeded Walking Access Directly to the Beach! New on the rental program - Beautifully updated 2-bedroom near the pool, t ...

    From $150 per night (USD)

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    Details
  • Island House
    From $475 per night (USD)

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    Island House

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    23

    Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! The health and sa ...

    From $475 per night (USD)

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    Details
  • Weybridge 44
    From $88 per night (USD)

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    Weybridge 44

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    2 Bedroom 2 Bathroom Condo with Lovely Lanai overlooking the golfcourse This property is in the Meadows golf and tennis ...

    From $88 per night (USD)

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  • Crescent Royale Siesta Key
    From $140 per night (USD)

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    Crescent Royale Siesta Key

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Beautiful condo at Crescent Royale for the very best price available! RECENTLY UPDATED - New Kitchen, granite, new bat ...

    From $140 per night (USD)

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    Details
  • Lemoness
    From $400 per night (USD)

    VRBO

    Lemoness

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Lemoness is a lovely, quiet place to experience the fullness of a Florida vacation. It's not the typical Florida vacat ...

    From $400 per night (USD)

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    Details
  • Single Family Home
    From $189 per night (USD)

    VRBO

    Single Family Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Welcome to our newly remodeled coastline home. Located in a desirable community of South Venice. Several beautiful beach ...

    From $189 per night (USD)

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    Details
  • 1/1 (072) Tower Gulf Front View W
    From $210 per night (USD)

    VRBO

    1/1 (072) Tower Gulf Front View W

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unit 72- 1 Bedroom 1 Bathroom Gulf Front Condominium. | This newly renovated, one bedroom one bathroom gulf front cond ...

    From $210 per night (USD)

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    Details
  • CA605N
    From $157 per night (USD)

    VRBO

    CA605N

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come spend a relaxing vacation in a true tropical paradise setting. You will soon see why Dr. Stephen P. Leatherman ("Dr ...

    From $157 per night (USD)

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    Details
  • Excelsior Beach to Bay Condos
    From $100 per night (USD)

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    Excelsior Beach to Bay Condos

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Deluxe Condo in a Tropical Courtyard Setting steps from the Beach. Our home features two bedrooms, pull-our couch with a ...

    From $100 per night (USD)

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    Details
  • Siesta Beach Condo
    From $85 per night (USD)

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    Siesta Beach Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Usted merece el tipo de conveniencia que ofrece nuestro condominio; no pierda el tiempo lidiando con problemas de estaci ...

    From $85 per night (USD)

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    Details
  • 1/1 (108) Tower Partial South Gulf View S
    From $190 per night (USD)

    VRBO

    1/1 (108) Tower Partial South Gulf View S

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unit 108- 1 Bedroom 1 Bathroom Condominium with Partial South Gulf Views. | This 1 bedroom 1 bathroom condominium is l ...

    From $190 per night (USD)

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    Details
  • Oak and Orchid
    From $120 per night (USD)

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    Oak and Orchid

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Completely remodeled in 2016, this house is full of everything new and always updating as we go. All new flooring (porce ...

    From $120 per night (USD)

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    Details
  •  Less than 2 Blocks to the Beach Heated Pool
    From $389 per night (USD)

    VRBO

    Less than 2 Blocks to the Beach Heated Pool

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    10

    Our housekeepers are taking proactive steps to sanitize entry points and heavily used areas to help stop the spread of C ...

    From $389 per night (USD)

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    Details
  • 2/2 (139) Club Corner
    From $220 per night (USD)

    VRBO

    2/2 (139) Club Corner

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 139- Remodeled Kitchen, easy care wood flooring and updated furnishings July 2018 | Entire living area and bedrooms ...

    From $220 per night (USD)

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    Details
  • 125 S Blvd. of Presidents
    From $550 per night (USD)

    VRBO

    125 S Blvd. of Presidents

    Bedrooms:
    6.5
    Bathrooms:
    5
    Sleeps:
    10

    Please see COVID and Standard Cancellation Policy below - it is different from VRBO policy options, as are payment opti ...

    From $550 per night (USD)

    VRBO

    Details
  • Walk to the Beach! Newly Remodeled w/ Patio, 4 Blocks from Venice Beaches
    From $59 per night (USD)

    VRBO

    Walk to the Beach! Newly Remodeled w/ Patio, 4 Blocks from Venice Beaches

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    We value the health and safety of all of our guests. All frequently touched surfaces, knobs, faucets, and appliances are ...

    From $59 per night (USD)

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    Details
  • Siesta Dunes
    From $231 per night (USD)

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    Siesta Dunes

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy breath taking sunsets with white sandy beaches at this completely renovated and newly updated condo with great Gul ...

    From $231 per night (USD)

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    Details
  • 9412GULFBAY102BGBCMCO - Gulf and Bay Club 102B
    From $99 per night (USD)

    VRBO

    9412GULFBAY102BGBCMCO - Gulf and Bay Club 102B

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ready to spend twenty-eight days or more in paradise? If so, Gulf & Bay Club 102B is waiting for you. This ground-floor ...

    From $99 per night (USD)

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    Details
  • Sea Shell Condo 106 2BRs 1Bath
    From $179 per night (USD)

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    Sea Shell Condo 106 2BRs 1Bath

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Come and sink your toes into the cool powdery white sand right outside your door, see the incredible sunsets and enjoy a ...

    From $179 per night (USD)

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    Details
  • 1/1 (102) Tower Gulf Front View W
    From $210 per night (USD)

    VRBO

    1/1 (102) Tower Gulf Front View W

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unit 102- 1 Bedroom 1 Bathroom Gulf Front Condominium. | Our Gulf front condo 1 bedroom 1 bathroom was fully renovated i ...

    From $210 per night (USD)

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    Details
  • Peppertree Bay
    From $55 per night (USD)

    VRBO

    Peppertree Bay

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy the Gulf of Mexico views from our recently renovated penthouse apartment on Siesta Key. You will have access to th ...

    From $55 per night (USD)

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    Details
  • 605 CS Tower 2BR 2BA Sleeps 6
    From $229 per night (USD)

    VRBO

    605 CS Tower 2BR 2BA Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Treat yourself to a completely remodeled and updated 6th floor 2 bedroom 2 bath ocean front condo. Enjoy the beautiful ...

    From $229 per night (USD)

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    Details
  • Siesta Villa Palma
    From $120 per night (USD)

    VRBO

    Siesta Villa Palma

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    5

    Covid-19 Altez Vacations is committed to the safety and well-being of its guests.  As such we have adopted additional c ...

    From $120 per night (USD)

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    Details
  • 2/2 (316) Bayside T Model
    From $180 per night (USD)

    VRBO

    2/2 (316) Bayside T Model

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This second floor 2-bedroom 2-bathroom condominium is located on the Bay side of our property. This unit requires a fiv ...

    From $180 per night (USD)

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    Details
  • 1/1 (114) Tower Partial North Gulf View N
    From $170 per night (USD)

    VRBO

    1/1 (114) Tower Partial North Gulf View N

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unit 114- 1 Bedroom 1 Bathroom Condominium with Partial North Gulf views. | This 1 bedroom 1 bathroom condominium is l ...

    From $170 per night (USD)

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    Details
  • SK private beach access
    From $329 per night (USD)

    VRBO

    SK private beach access

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Beachside, spacious 3 bedroom, 2500 square feet, beach townhouse located among the resort community of Sara Sea Circle w ...

    From $329 per night (USD)

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    Details
  • Mid-century Waterfront Home with heated pool
    From $500 per night (USD)

    VRBO

    Mid-century Waterfront Home with heated pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Mid-century home located midway between Sarasota and Venice FL. Peaceful views of South creek flowing into the Sarasota ...

    From $500 per night (USD)

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    Details
  • Luxury Beach Location
    From $475 per night (USD)

    VRBO

    Luxury Beach Location

    Bedrooms:
    5.5
    Bathrooms:
    3
    Sleeps:
    8

    One of the nicest private homes on Siesta Key Beach. We have the highest 5 star rating on Siesta Key. See Vrbo 80254 ...

    From $475 per night (USD)

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    Details
  • 2/2 (349) Bayside T Model
    From $180 per night (USD)

    VRBO

    2/2 (349) Bayside T Model

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This second floor newly renovated 2-bedroom 2-bathroom condominium is located on the Bayside of our property. The Baysi ...

    From $180 per night (USD)

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    Details
  • 2/2 (141) Club Interior
    From $200 per night (USD)

    VRBO

    2/2 (141) Club Interior

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 141- Totally Remodelled! Unit 141. Gulfside. 2 Min Walk To Beach/Short Dr To Village | Located in desirable, famil ...

    From $200 per night (USD)

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    Details
  • Contento Circle Vacation Home
    From $300 per night (USD)

    VRBO

    Contento Circle Vacation Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This is a beautiful tropically landscaped, completely updated & renovated Siesta Key Home. It features spacious vaulted ...

    From $300 per night (USD)

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    Details
  • Top Rated Gulf Side, Steps from Beach, Great Amenities 2 pools, tennis, hot tub
    From $100 per night (USD)

    VRBO

    Top Rated Gulf Side, Steps from Beach, Great Amenities 2 pools, tennis, hot tub

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    NOT YOUR GRANDMA'S CONDO! Our 2BR/2BA condo is on the gulf side of Palm Bay Club, one of the most sought-after properti ...

    From $100 per night (USD)

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    Details
  • 307 CS Tower 2BR 2BA Sleeps 6
    From $229 per night (USD)

    VRBO

    307 CS Tower 2BR 2BA Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    A luxurious two-bedroom, two bath unit beautifully redecorated! Sit and relax on the lanai and enjoy the spectacular vi ...

    From $229 per night (USD)

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    Details
  • Condo 107 Experience Paradise
    From $199 per night (USD)

    VRBO

    Condo 107 Experience Paradise

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come and sink your toes into the cool powdery white sand right outside your door, see the incredible sunsets and enjoy a ...

    From $199 per night (USD)

    VRBO

    Details
  • 710 CS Tower 2BR 2 BA Sleeps 6
    From $214 per night (USD)

    VRBO

    710 CS Tower 2BR 2 BA Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...

    From $214 per night (USD)

    VRBO

    Details
  • Starling's Nest, The Landings
    From $150 per night (USD)

    VRBO

    Starling's Nest, The Landings

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Looking for the perfect Florida vacation retreat in Sarasota’s most desired gat3 communities? Perfect, newly renovated t ...

    From $150 per night (USD)

    VRBO

    Details
  • The Palms on Shamrock Drive
    From $40 per night (USD)

    VRBO

    The Palms on Shamrock Drive

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    As you step through the front door, you're welcomed by the soothing coastal charm of a newly decorated and fully updated ...

    From $40 per night (USD)

    VRBO

    Details
  • SAFE / CLEAN comfortable home.
    From $150 per night (USD)

    VRBO

    SAFE / CLEAN comfortable home.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    NEW! Take a break from the everyday life in wonderful Sarasota and treat yourself to stay at this vacation rental! Be am ...

    From $150 per night (USD)

    VRBO

    Details
  • Bella Villino
    From $60 per night (USD)

    VRBO

    Bella Villino

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ubicado en el atractivo Palmer Ranch, Sarasota, este condominio muy limpio y meticulosamente cuidado de 2 habitaciones, ...

    From $60 per night (USD)

    VRBO

    Details
  • Gulf Gate: Designer 3/2 split plan, 4 min to Siesta Lg yard for dogs to run/play
    From $100 per night (USD)

    VRBO

    Gulf Gate: Designer 3/2 split plan, 4 min to Siesta Lg yard for dogs to run/play

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    (NOTE: Photos will be replaced with professional ones soon!) Sleeps 6. Light and Bright 1740 sq. ft. Just renovated Mid ...

    From $100 per night (USD)

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    Details
  • 2/2 (113) Tower Gulf Front View NW
    From $300 per night (USD)

    VRBO

    2/2 (113) Tower Gulf Front View NW

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 113- 2 Bedroom 2 Bathroom Gulf Front Condominium. | This two bedroom two bathroom Gulf Front view condominium is ...

    From $300 per night (USD)

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    Details
  • 2/2 (043) Tower Gulf Front View NW
    From $300 per night (USD)

    VRBO

    2/2 (043) Tower Gulf Front View NW

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 43- 2 Bedroom and 2 Bathroom Gulf Front Condominium | This beautiful two bedroom two bathroom Gulf front view cond ...

    From $300 per night (USD)

    VRBO

    Details
  • Sandhill Preserve, Sarasota
    From $299 per night (USD)

    VRBO

    Sandhill Preserve, Sarasota

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Live in paradise! Beautiful, brand new home in a prestigious and picturesque, 24-hr gated community located in desirabl ...

    From $299 per night (USD)

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    Details
  • 5855 Mignight Pass
    From $120 per night (USD)

    VRBO

    5855 Mignight Pass

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    We speak English,Czech,Slovak and Polish! Enter the ultimate paradise! Siesta Key in Sarasota is known by its beautiful ...

    From $120 per night (USD)

    VRBO

    Details
  • 2/2 (175) Club Corner
    From $220 per night (USD)

    VRBO

    2/2 (175) Club Corner

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Palm Bay Club 175, a spacious 2 bedroom 2 bath condo | *Newly remodeled unit with new designer tile installed throughout ...

    From $220 per night (USD)

    VRBO

    Details
  • Sunset Royale, Condo 304
    From $175 per night (USD)

    VRBO

    Sunset Royale, Condo 304

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    HERE'S 23 TOP REASONS why This Condo Unit is the Perfect Place to Stay for Your Siesta Key Vacation. Also, read below ...

    From $175 per night (USD)

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    Details
  • Siesta Harbor
    From $210 per night (USD)

    VRBO

    Siesta Harbor

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Water views and peace and quiet are what you will enjoy in this charming one-bedroom, two-bath ground floor condo in a 5 ...

    From $210 per night (USD)

    VRBO

    Details
  • 2/2 (174) Club Corner
    From $220 per night (USD)

    VRBO

    2/2 (174) Club Corner

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautifully Remodeled Unit! | A 2 bedroom 2 bathroom Club Corner Suite located on the 2nd floor on the Gulf of Mexico si ...

    From $220 per night (USD)

    VRBO

    Details
  • The Beach Loft
    From $100 per night (USD)

    VRBO

    The Beach Loft

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    6

    Book now and enjoy this newly renovated Light & Bright condo with premium features. Everything in this condo "came out o ...

    From $100 per night (USD)

    VRBO

    Details
  • Gisèle's House - Calle Florida
    From $450 per night (USD)

    VRBO

    Gisèle's House - Calle Florida

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    **Stay more then 28 days in September and October 2021, get 25% the daily rate ** ** 3 month stay (Sept, Oct & Nov 2021 ...

    From $450 per night (USD)

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  • Jamaica Royale (Unit #100)
    From $99 per night (USD)

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    Jamaica Royale (Unit #100)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Due to the COVID-19 virus, I am adding one additional step to the cleaning process in this condo. Until further notice ...

    From $99 per night (USD)

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  • Aloft on Canal
    From $500 per night (USD)

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    Aloft on Canal

    Bedrooms:
    7.5
    Bathrooms:
    8
    Sleeps:
    22

    Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! The health and sa ...

    From $500 per night (USD)

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  • Gisèle's House - Cape Leyte
    From $450 per night (USD)

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    Gisèle's House - Cape Leyte

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Come enjoy this private house with your own secluded heated swimming pool, in beautiful Siesta Key. Rent for a stay of ...

    From $450 per night (USD)

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  • Casa Tropical
    From $179 per night (USD)

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    Casa Tropical

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Just 2 miles to Siesta Key, this 4 bed/3 bath home is the perfect place to escape with a large group! This charming hom ...

    From $179 per night (USD)

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  • 1/1 (028) Tower Partial South Gulf View S
    From $190 per night (USD)

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    1/1 (028) Tower Partial South Gulf View S

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unit 28- 1 Bedroom, 1 Bathroom Condo With Beautiful Beach And Gulf View | Voted America's #1 Beach, experience your own ...

    From $190 per night (USD)

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  • Tiki on the Bay
    From $65 per night (USD)

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    Tiki on the Bay

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy the Tropical Setting in This Restored Fishing Cottage with Direct Bay front Views! All the Comforts You Want and ...

    From $65 per night (USD)

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  • Crescent Royale Condominiums
    From $170 per night (USD)

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    Crescent Royale Condominiums

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Premier 2 Bed/Bath with large Pool. Directly across the street from Siesta Beach! This fifth floor unit offers a spe ...

    From $170 per night (USD)

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  • Sea Club 2
    From $125 per night (USD)

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    Sea Club 2

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wonderful stand alone cottage ready for your perfect retreat! Master bedroom has a king size bed, full private bathroom ...

    From $125 per night (USD)

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  • The Good Life
    From $150 per night (USD)

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    The Good Life

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Check out our reviews. You will not be disappointed!! Welcome to the "Good Life" - your Siesta Key private home just a ...

    From $150 per night (USD)

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  • LIDO BEACH 1BR/1.5BA CONDO
    From $75 per night (USD)

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    LIDO BEACH 1BR/1.5BA CONDO

    Bedrooms:
    2.5
    Bathrooms:
    1
    Sleeps:
    4

    1 Bedroom, 1 full bath and one half bath, 4th floor condominium with screened in balcony and partial water views. Recen ...

    From $75 per night (USD)

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  • Siesta Sun Villas Seahorse
    From $25 per night (USD)

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    Siesta Sun Villas Seahorse

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    We are a small resort on Siesta Key offering daily rentals Sea horse villa is perfect for a couple or single traveler. ...

    From $25 per night (USD)

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  • Sea Shell Condo 310 Spacious f
    From $228 per night (USD)

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    Sea Shell Condo 310 Spacious f

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come and sink your toes into the cool powdery white sand right outside your door, see the incredible sunsets and enjoy a ...

    From $228 per night (USD)

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  • The Charles Ringling Room
    From $107 per night (USD)

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    The Charles Ringling Room

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Just minutes from beautiful Sarasota Bay and lovely beaches! This guest room, a king, 1 BR with private bath and kitche ...

    From $107 per night (USD)

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  • Huge Home with Screened Pool | Walk to Lido Beach
    From $314 per night (USD)

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    Huge Home with Screened Pool | Walk to Lido Beach

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Make a splash in the private screened-in pool of this 4BR/4BA home. Lounge with a book in the cozy sunroom. Kids and adu ...

    From $314 per night (USD)

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  • Island Suite
    From $95 per night (USD)

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    Island Suite

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Next to the Siesta Key Public Beach, 60 steps only! The charming and recently refurbished & updated 2 bedroom apartment ...

    From $95 per night (USD)

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  • Feeling at Home on Siesta Key
    From $100 per night (USD)

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    Feeling at Home on Siesta Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This charming home has everything you need to make your stay comfortable and relaxing. It only takes a few minutes to b ...

    From $100 per night (USD)

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  • FLAMINGO
    From $234 per night (USD)

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    FLAMINGO

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Bask in the sunshine on South Venice's private beach, (reachable only by a private 20 passenger ferry) or splash in the ...

    From $234 per night (USD)

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  • Sea Winds 205
    From $159 per night (USD)

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    Sea Winds 205

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Siesta Key located on the Gulf of Mexico. Tropical beauty with white powder sand, gorgeous sunsets, pristine waters and ...

    From $159 per night (USD)

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  • 2/2 (025) Tower NE
    From $260 per night (USD)

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    2/2 (025) Tower NE

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 25 Grand Tower on the Beach- View of the neighboring sea grapes | Voted America's #1 Beach!! Turn up the volume a ...

    From $260 per night (USD)

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  • 2/2 (332) Bayfront C Model
    From $220 per night (USD)

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    2/2 (332) Bayfront C Model

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 332- 2 Bedroom 2 Bathroom Bay Front View Large Condominium. | This newly renovated third floor Bay Front 2-bedroo ...

    From $220 per night (USD)

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  • Playalido Unit #1
    From $60 per night (USD)

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    Playalido Unit #1

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Playa Lido Unit 1 is a 1bedroom with queen size bed, living room with queen size sleep-sofa, full kitchen, WiFi and flat ...

    From $60 per night (USD)

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  • Manasota Key Dream Beach House
    From $140 per night (USD)

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    Manasota Key Dream Beach House

    Bedrooms:
    4.5
    Bathrooms:
    5
    Sleeps:
    12

    Stay by the beach! Tucked under a canopy of old-growth shade oaks, this is true Key-West-style, beach area home with a ...

    From $140 per night (USD)

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  • Best Views from Harbor Towers on Siesta Key
    From $90 per night (USD)

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    Best Views from Harbor Towers on Siesta Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Please note the Condo Association requires a two week minimum rental period. Rather than require a security deposit, the ...

    From $90 per night (USD)

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    Details
  • Siesta Key Red Door House
    From $220 per night (USD)

    VRBO

    Siesta Key Red Door House

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This is a cozy four bedroom house. The smaller 4th bedroom can be used as an office. We offer free WiFi, free guest park ...

    From $220 per night (USD)

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  • Garden Cottage
    From $200 per night (USD)

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    Garden Cottage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    have your own tropical garden hide away in the heart of Sarasota. quiet and newly-remodeled. Everything is new and well ...

    From $200 per night (USD)

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  • The Shells Villa
    From $391 per night (USD)

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    The Shells Villa

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    10

    As you enter the Shells Villa for the first time you know you are not in a typical vacation home. From the Spanish tile ...

    From $391 per night (USD)

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  • The Mable Ringling Loft
    From $107 per night (USD)

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    The Mable Ringling Loft

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Just minutes from beautiful Sarasota Bay and lovely beaches! This upstairs guest room, a 1 BR king with private bath is ...

    From $107 per night (USD)

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  • A Shore Thing
    From $200 per night (USD)

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    A Shore Thing

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    8

    Gorgeous 3,000+ square foot, three bedroom plus bonus room, 2 1/2 bath updated beach house on wooded one acre grounds di ...

    From $200 per night (USD)

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  • 805 CS Tower 2BR 2 BA Sleeps 4
    From $214 per night (USD)

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    805 CS Tower 2BR 2 BA Sleeps 4

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...

    From $214 per night (USD)

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  • 2/2 (135) Club Corner
    From $220 per night (USD)

    VRBO

    2/2 (135) Club Corner

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This first floor 2 bedroom 2 bathroom, condominium is located on the Gulf side of our property. Because of its central l ...

    From $220 per night (USD)

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  • Siesta Key Heritage House
    From $300 per night (USD)

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    Siesta Key Heritage House

    Bedrooms:
    4.5
    Bathrooms:
    4
    Sleeps:
    8

    Now currently accepting reservations for 2022. Fully booked for 2021. Located in the exclusive Palm Island enclave 2. ...

    From $300 per night (USD)

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  • 404S
    From $100 per night (USD)

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    404S

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy the tranquil sound of ocean waves lapping the shore while a gentle summer breeze flows throughout this beachfront ...

    From $100 per night (USD)

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  • Sunny Sarasota Vacation Home
    From $225 per night (USD)

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    Sunny Sarasota Vacation Home

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    This beautiful home includes 4 bedrooms, 2 bathrooms and sleeps up to 10 people. Near #1 Rated SIESTA KEY BEACH & LIDO ...

    From $225 per night (USD)

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  • Sarasota Palmhouse
    From $275 per night (USD)

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    Sarasota Palmhouse

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Renovated, designer-owned, 3 bedroom property featuring modern architecture, mid-century inspired furnishings and origin ...

    From $275 per night (USD)

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    Details