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  • Sunset View
    From $215 per night (USD)

    VRBO

    Sunset View

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Relax and enjoy a 5 star luxury home, built in 2011, which is not overlooked by any other homes. Manasota Beach, with fr ...

    From $215 per night (USD)

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    Details
  • The Sandcastle Villa
    From 79 € per night (EUR)

    VRBO

    The Sandcastle Villa

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The Sandcastle Villa is a luxurious house in a prime location. It has upscale features with a covered (mosquito protecte ...

    From 79 € per night (EUR)

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    Details
  • Casa Daniela
    From 320 € per night (EUR)

    VRBO

    Casa Daniela

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Our lovingly renovated and modern pool house is located in a quiet residential area in Venice Gardens. It is equipped w ...

    From 320 € per night (EUR)

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    Details
  • Siesta Key Getaway
    From $89 per night (USD)

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    Siesta Key Getaway

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The condo is on the third floor balcony facing south overlooking the mediterainian garden. At almost 1400 square feet, t ...

    From $89 per night (USD)

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    Details
  • Pool Villa II + Privat-Strand
    From $175 per night (USD)

    VRBO

    Pool Villa II + Privat-Strand

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    COVID-19 Information: We follow the new CDC cleaning and sanitation guidelines for Vacation rentals! My Pool Villa's ar ...

    From $175 per night (USD)

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    Details
  • Villa-Happy-Holiday
    From $100 per night (USD)

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    Villa-Happy-Holiday

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Description of Holiday House Happy Holiday in North Port Location of the holiday home The house is conveniently located ...

    From $100 per night (USD)

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    Details
  • Villa Gecko
    From 260 € per night (EUR)

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    Villa Gecko

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Den snyggt inredda, avskilt Villa Gecko är i ett lugnt läge. De cirka 140 kvm boyta med 3 sovrum och 2 badrum kan bekväm ...

    From 260 € per night (EUR)

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    Details
  • Florida Pool Villa Happy Gator
    From $160 per night (USD)

    VRBO

    Florida Pool Villa Happy Gator

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    COVID-19 Information: We follow the new CDC cleaning and sanitation guidelines for Vacation rentals! Our Villa Happy G ...

    From $160 per night (USD)

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    Details
  • VeniceIsland Golden Beach home
    From $200 per night (USD)

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    VeniceIsland Golden Beach home

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Our home is located in one of the nicest and sought after Island of Venice neighborhoods: Golden Beach The house is in ...

    From $200 per night (USD)

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    Details
  • Villa Lemon Tree
    From $150 per night (USD)

    VRBO

    Villa Lemon Tree

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    During the corona Crisis we offer our guests to refund 100% if the house cannot be used because of rental or travel bans ...

    From $150 per night (USD)

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    Details
  • Villa the place
    From $160 per night (USD)

    VRBO

    Villa the place

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Our house was completed in August 2018 and we are pleased to introduce our new building. The house is 184 m², has 3 bedr ...

    From $160 per night (USD)

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    Details
  • Villa Buttonwood Longboat Key
    From $190 per night (USD)

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    Villa Buttonwood Longboat Key

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Huset har cirka 220 kvadratmeter bostadsyta, som är fördelat på 2 våningar. Från den ljusa, stora vardags- / matplatsen, ...

    From $190 per night (USD)

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    Details
  • Pool Villa I + Privat-Strand
    From $175 per night (USD)

    VRBO

    Pool Villa I + Privat-Strand

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    COVID-19 Information: We follow the new CDC cleaning and sanitation guidelines for Vacation rentals! My Pool Villa's ar ...

    From $175 per night (USD)

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    Details
  • Villa Nectar
    From $140 per night (USD)

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    Villa Nectar

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    We are pleased to welcome you in our completely renovated modern villa with solar heated private pool, outdoor kitchen, ...

    From $140 per night (USD)

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    Details
  • Newly Remodeled!  Directly Across from Beach ~ Condo
    From $113 per night (USD)

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    Newly Remodeled! Directly Across from Beach ~ Condo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The location of the condo is fantastic as you will have access to the luxurious Longboat Key Beach nearly to yourself. T ...

    From $113 per night (USD)

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    Details
  • 2/2 (041) Tower Gulf Front View SW
    From $300 per night (USD)

    VRBO

    2/2 (041) Tower Gulf Front View SW

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 41- 2 Bedroom and 2 Bathroom Gulf Front Condominium. | A two bedroom two bathroom Gulf front view condo located on ...

    From $300 per night (USD)

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    Details
  • Harbor Towers & Yacht and Racquet Club
    From $100 per night (USD)

    VRBO

    Harbor Towers & Yacht and Racquet Club

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Harbor Towers Yacht and Racquet Club is located on the inter-coastal waterway on Siesta Key in Sarasota, Florida. From t ...

    From $100 per night (USD)

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    Details
  • BEAUTIFUL CONDO NEAR SIESTA
    From $100 per night (USD)

    VRBO

    BEAUTIFUL CONDO NEAR SIESTA

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    ASK ABOUT OUR MONTHLY RATES. Our goal is to make your stay as pleasant and comfortable as you would stay at your own ho ...

    From $100 per night (USD)

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    Details
  • Cozy Cottage
    From $50 per night (USD)

    VRBO

    Cozy Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This is a 2 bedroomed, one bath house, centrally located near downtown Sarasota, pet friendly within walking distance to ...

    From $50 per night (USD)

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    Details
  •  Siesta Key Waterfront Condo
    From $219 per night (USD)

    VRBO

    Siesta Key Waterfront Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This spacious first floor waterfront condo has over 1879 sq. of indoor/outdoor living space. Boasting two gigantic eleva ...

    From $219 per night (USD)

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    Details
  • CA202S
    From $193 per night (USD)

    VRBO

    CA202S

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our second floor, gulf-front apartment offers a spectacular, uninterrupted view down beautiful Crescent Beach. Located o ...

    From $193 per night (USD)

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    Details
  • Siesta Leona House in Village
    From $175 per night (USD)

    VRBO

    Siesta Leona House in Village

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Introducing, a deluxe vacation property in the Village of Siesta on the intercoastal waterway. Key features include, hea ...

    From $175 per night (USD)

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    Details
  • Palm Bay Club Unit 24
    From $150 per night (USD)

    VRBO

    Palm Bay Club Unit 24

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unit G-24 is a beach style condo on the second floor Grand Tower with a private beach access. Take an elevator or stairs ...

    From $150 per night (USD)

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    Details
  • Peaceful Venice Pool Home with Private Beach Access
    From $50 per night (USD)

    VRBO

    Peaceful Venice Pool Home with Private Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    "Sister house" to listing 284113, this home is just two doors down and owned by the same meticulous homeowners. Just li ...

    From $50 per night (USD)

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    Details
  • 1/1 (068) Tower Partial South Gulf View S
    From $190 per night (USD)

    VRBO

    1/1 (068) Tower Partial South Gulf View S

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unit 68- 1 Bedroom and 1 Bathroom Condominium with Partial South Views. | There are spectacular views from this beauti ...

    From $190 per night (USD)

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    Details
  • Home is where the Beach is
    From $650 per night (USD)

    VRBO

    Home is where the Beach is

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    6

    The address of this property is: 1345 Fundy Road, Venice, FL, 34293. Newly remodeled, 3 bedroom, 2,5 bath house with an ...

    From $650 per night (USD)

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    Details
  • Gulf Gate Garden Homes Villa
    From $110 per night (USD)

    VRBO

    Gulf Gate Garden Homes Villa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This is our newly redecorated, 1340 square -foot, 'Old Florida' villa, with all new kitchen appliances. Across the fro ...

    From $110 per night (USD)

    VRBO

    Details
  • 226 N Blvd of  Presidents
    From $500 per night (USD)

    VRBO

    226 N Blvd of Presidents

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    11

    Please see COVID / STANDARD CANCELLATION POLICY BELOW - it is different from VRBO policy options as are payment options ...

    From $500 per night (USD)

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    Details
  • 2/2 (322) Bayside B Model
    From $200 per night (USD)

    VRBO

    2/2 (322) Bayside B Model

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Palm Bay Club Unit #322 Lg Bay Front Unit. Completely Updated Unit | Large Two Bedroom/ Two Bath Unit Overlooking The Ba ...

    From $200 per night (USD)

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    Details
  • Siesta Key Peppertree Bay Beach front Cono
    From $250 per night (USD)

    VRBO

    Siesta Key Peppertree Bay Beach front Cono

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    4

    30 day minimum stay . 3 month minimum off season May to December ESCAPE TO GORGEOUS SIESTA KEY and stay RIGHT ON THE ...

    From $250 per night (USD)

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    Details
  • CS Villa 15 2BR 2BA Sleeps 5
    From $243 per night (USD)

    VRBO

    CS Villa 15 2BR 2BA Sleeps 5

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    This 2 bedroom 2 bath villa provides Gracious living with touches of luxury in this completely equipped apartment with p ...

    From $243 per night (USD)

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    Details
  • 1/1 (048) Tower Partial South Gulf View S
    From $190 per night (USD)

    VRBO

    1/1 (048) Tower Partial South Gulf View S

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unit 48- 1 Bedroom and 1 Bathroom Condominium with Partial South Gulf Views. | This 1 bedroom 1 bathroom condominium l ...

    From $190 per night (USD)

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    Details
  • Poolside Paradise Condo
    From $47 per night (USD)

    VRBO

    Poolside Paradise Condo

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    This bright and relaxing condo includes 2 bedroom (1 King) (1 Full/Twin bunk bed) Full kitchen including dishwasher, cof ...

    From $47 per night (USD)

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    Details
  • 440 Bird Key Drive
    From $700 per night (USD)

    VRBO

    440 Bird Key Drive

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    6

    The 2329 sq ft Mediterranean style ranch house is located on Bird Key in the middle of Sarasota Bay. Bird Key is a sec ...

    From $700 per night (USD)

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    Details
  • Crescent Arms
    From $75 per night (USD)

    VRBO

    Crescent Arms

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    New Sliding glass doors installed May 2020. All trim work newly painted and caulking throughout. New AC May 2021, new ...

    From $75 per night (USD)

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    Details
  • 2850 Gulf of Mexico Dr #3
    From $125 per night (USD)

    VRBO

    2850 Gulf of Mexico Dr #3

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The condo directly across the street from the public beach access. This is a very private part of Longboat and often y ...

    From $125 per night (USD)

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    Details
  • 2/2 (164) Club Corner
    From $220 per night (USD)

    VRBO

    2/2 (164) Club Corner

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 164- Fully Equipped. Bright, Private Beach, Pool, 2/2, 2,200 sq ft Balcony | This condo really does have everything ...

    From $220 per night (USD)

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    Details
  • Casa El SueƱo
    From $35 per night (USD)

    VRBO

    Casa El Sueño

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Located just across from Siesta Key, on the mainland of Sarasota, you have access to all the city offers and are only a ...

    From $35 per night (USD)

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    Details
  • 2/2 (033) Tower Gulf Front View NW
    From $300 per night (USD)

    VRBO

    2/2 (033) Tower Gulf Front View NW

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 33- 2 Bedroom and 2 Bathroom Gulf Front Condominium | | Unit 33 is a two bedroom two bathroom sleeps six people ma ...

    From $300 per night (USD)

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    Details
  • Salty Dog
    From $475 per night (USD)

    VRBO

    Salty Dog

    Bedrooms:
    6.5
    Bathrooms:
    6
    Sleeps:
    17

    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
  • Sea Sun Fun!
    From $279 per night (USD)

    VRBO

    Sea Sun Fun!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    A perfect relaxation destination for two! This location has everything. Five minutes walk to the beautiful Lido Beach an ...

    From $279 per night (USD)

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    Details
  • Casa Mar Resort
    From $150 per night (USD)

    VRBO

    Casa Mar Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    If you love to walk or run along the beach in the morning, sun tan on soft, white sand in the afternon, and watch specta ...

    From $150 per night (USD)

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    Details
  • Sabel Trace
    From $50 per night (USD)

    VRBO

    Sabel Trace

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Clean and spacious furnished property over looking wild life area. Beautiful pool and patio area. Close to shopping an ...

    From $50 per night (USD)

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    Details
  • Chateau Village 104
    From $75 per night (USD)

    VRBO

    Chateau Village 104

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Be sure to check out our other properties 512091- Living the Dream on Lido I 2086500 - Sunshine on Lido (New Listing) + ...

    From $75 per night (USD)

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    Details
  • Ibis Paradise-2br/2ba LOVELY
    From $150 per night (USD)

    VRBO

    Ibis Paradise-2br/2ba LOVELY

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We've enjoyed visiting Venice for many years and decided to purchase a beautiful golf course condo. The area offers worl ...

    From $150 per night (USD)

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    Details
  • 9. 3252 MAYFLOWER ST
    From $309 per night (USD)

    VRBO

    9. 3252 MAYFLOWER ST

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your Sarasota Vacation Home in Gulf Gate close to Siesta Beach! Newly remodeled 3 bedrooms and 2 baths. 2 be ...

    From $309 per night (USD)

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    Details
  • Sarasota Sandpiper
    From $400 per night (USD)

    VRBO

    Sarasota Sandpiper

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    This wonderful pool home is located in the heart of Sarasota and just minutes away from the world-famous Siesta Key Beac ...

    From $400 per night (USD)

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    Details
  • Beach Cottage - 1 Bedroom
    From $134 per night (USD)

    VRBO

    Beach Cottage - 1 Bedroom

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    ***CANCELLATION POLICY WAIVED FOR CORONAVIRUS. ***CANCELLATION POLICY WAIVED FOR RED TIDE. ***MAXIMUM CAPACITY OF 2 IS ...

    From $134 per night (USD)

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    Details
  • Casa Playa SK
    From $244 per night (USD)

    VRBO

    Casa Playa SK

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    - Location, location, location! We are steps away from the beach and village. - Walk or bike EVERYWHERE and leave your ...

    From $244 per night (USD)

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    Details
  • The Shore House
    From $500 per night (USD)

    VRBO

    The Shore House

    Bedrooms:
    5.5
    Bathrooms:
    7
    Sleeps:
    19

    The Best Homes, Location and Vacation Experience on Lido Key! *Due to Lido Key rental code, this property must be rente ...

    From $500 per night (USD)

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    Details
  • LJ St. Armands
    From $150 per night (USD)

    VRBO

    LJ St. Armands

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Beautiful 3 bedroom 3 bath home. Ideally located steps from St Armand's Circle shops and restaurants and minutes from do ...

    From $150 per night (USD)

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    Details
  • Siesta Key Pool House
    From $1420 per night (USD)

    VRBO

    Siesta Key Pool House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    The house is located within 10 minutes drive from both downtown and Siesta Keys beach, and about 20 minutes drive from L ...

    From $1420 per night (USD)

    VRBO

    Details
  • Englewood Cottage
    From $250 per night (USD)

    VRBO

    Englewood Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Adorable completely renovated and remodeled cottage in downtown historic Englewood area. Experience "Old Florida" at it' ...

    From $250 per night (USD)

    VRBO

    Details
  • Tiny House - Flamingo
    From $70 per night (USD)

    VRBO

    Tiny House - Flamingo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Your next vacation can have the relaxation of the beach with the cozy environment of Tiny House Flamingo. Flamingo once ...

    From $70 per night (USD)

    VRBO

    Details
  • 2/2 (359) Bayside T Model
    From $180 per night (USD)

    VRBO

    2/2 (359) Bayside T Model

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This third floor 2-bedroom 2-bathroom condominium is located on the Bay side of our property. The Bay side has a pool, ...

    From $180 per night (USD)

    VRBO

    Details
  • Inn on the Beach 2207
    From $85 per night (USD)

    VRBO

    Inn on the Beach 2207

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This perfect island getaway is located on the southern tip of Longboat Key with a beautiful beach and pool area. ...

    From $85 per night (USD)

    VRBO

    Details
  • 1/1 (104) Tower Partial North Gulf View N
    From $170 per night (USD)

    VRBO

    1/1 (104) Tower Partial North Gulf View N

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Completely renovated 1 Bedroom 1 Bathroom Condo- Amazing view of the #1 Beach from the Open Patio!! (Unit 104) | Relax ...

    From $170 per night (USD)

    VRBO

    Details
  • Pin Oak (Cottage 7A)
    From $80 per night (USD)

    VRBO

    Pin Oak (Cottage 7A)

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Slip into Old Florida Living at Pin Oaks Cottage at Sea Club 2, enjoying the ultimate R&R to accompany your exciting and ...

    From $80 per night (USD)

    VRBO

    Details
  • Bougainvillea Getaway
    From $250 per night (USD)

    VRBO

    Bougainvillea Getaway

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Súper lindo estilo de casa de playa en el barrio de Southgate, cerca de todo! Plano de planta dividido - 3 dormitorios ...

    From $250 per night (USD)

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    Details
  • s!Great VALUE!Heated Pool!SPRING SEASON SPECIAL, CLOSE TO SIESTA KEY, Free WiFi!
    From $325 per night (USD)

    VRBO

    s!Great VALUE!Heated Pool!SPRING SEASON SPECIAL, CLOSE TO SIESTA KEY, Free WiFi!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Don't Miss this Unique Opportunity to Rent Just Minutes from the White Sandy Beaches of Sparkling Siesta Key! My fully ...

    From $325 per night (USD)

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    Details
  • Sea You Soon in Venice
    From $100 per night (USD)

    VRBO

    Sea You Soon in Venice

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $100 per night (USD)

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    Details
  • 9412SIESTADUNE201SDWCO - Siesta Dunes Beach 201
    From $93 per night (USD)

    VRBO

    9412SIESTADUNE201SDWCO - Siesta Dunes Beach 201

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This unit has been newly renovated. Stunning seaside decor, new kitchen, baths, paint, and luxury vinyl plank flooring t ...

    From $93 per night (USD)

    VRBO

    Details
  • Peaceful Garden Oasis 2 Miles From #1  Beach In The USA
    From $125 per night (USD)

    VRBO

    Peaceful Garden Oasis 2 Miles From #1 Beach In The USA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Charming home with beautiful furnishings and artwork throughout. Large Master bedroom with king size bed, master bathroo ...

    From $125 per night (USD)

    VRBO

    Details
  • Breezy Villa
    From $349 per night (USD)

    VRBO

    Breezy Villa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Breezy Villa features two bedrooms and two baths with a tile floor throughout. There is a split floor plan with each be ...

    From $349 per night (USD)

    VRBO

    Details
  • Siesta Dunes
    From $143 per night (USD)

    VRBO

    Siesta Dunes

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We welcome you to relax and enjoy this bright, quiet, first floor, end unit offering park like views. The pool, sundeck ...

    From $143 per night (USD)

    VRBO

    Details
  • Jennings Drive Gem
    From $120 per night (USD)

    VRBO

    Jennings Drive Gem

    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 $120 per night (USD)

    VRBO

    Details
  • 2/2 (355) Bayside T Model
    From $180 per night (USD)

    VRBO

    2/2 (355) Bayside T Model

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This second floor 2-bedroom 2-bathroom condominium is located on the Bay side of our property. The Bay side has a pool, ...

    From $180 per night (USD)

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  • Hillview On The Park
    From $409 per night (USD)

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    Hillview On The Park

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    A live-oak canopy gives a tree house feel throughout this charming and centrally located 2 story home on the beautiful C ...

    From $409 per night (USD)

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  • Calypso
    From $250 per night (USD)

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    Calypso

    Bedrooms:
    4.5
    Bathrooms:
    4
    Sleeps:
    8

    This exclusive beach house is located on the waters edge, directly on the Gulf of Mexico on prestigious Longboat Key. Wh ...

    From $250 per night (USD)

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  • Shelly's Beach House
    From $250 per night (USD)

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    Shelly's Beach House

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Ocean paradise awaits you in this large, 5 bedroom/3 bath, open floor planned beach house with screened-in heated pool a ...

    From $250 per night (USD)

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  • Sea Turtle Bungalow
    From $85 per night (USD)

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    Sea Turtle Bungalow

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    You'll love the stunning brand new interior and excellent location of this house. Excellent location near Ringling Mus ...

    From $85 per night (USD)

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  • 1. 2880 Bahia Vista St
    From $259 per night (USD)

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    1. 2880 Bahia Vista St

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Conveni ...

    From $259 per night (USD)

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  • 2/2 (364) Bayside B Model
    From $200 per night (USD)

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    2/2 (364) Bayside B Model

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Palm Bay Club Bayside 364 is a 2 Bedroom 2 Bathroom Large Condominium with washer/dryer. This spacious corner suite con ...

    From $200 per night (USD)

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  • Venice Island Beach Home
    From $245 per night (USD)

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    Venice Island Beach Home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This home is located less than a mile from the beaches and downtown main street. Each room has been decorated in a diff ...

    From $245 per night (USD)

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    Details
  • Sunset Royale
    From $135 per night (USD)

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    Sunset Royale

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This newly renovated 1 bedroom condo accommodates 4 guests comfortably. Great for families due to the proximity of the b ...

    From $135 per night (USD)

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  • Completely newly remodelled
    From $120 per night (USD)

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    Completely newly remodelled

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to our completely remodelled 2bdrm/2 bath villa.Brand new kitchen with granite counters and stainless steel Sams ...

    From $120 per night (USD)

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  • 1/1.5 (147) Club Gulfside
    From $150 per night (USD)

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    1/1.5 (147) Club Gulfside

    Bedrooms:
    2.5
    Bathrooms:
    1
    Sleeps:
    4

    ***New Photos Coming Soon!*** This third floor 1 bedroom 1 1/2 bathroom condominium is located on the Gulf side of our p ...

    From $150 per night (USD)

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  • Siesta Key-Palm Island House
    From $400 per night (USD)

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    Siesta Key-Palm Island House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This adorable 3BR/2BA home is located in the quiet neighborhood of Palm Island, just a short walk away from the world fa ...

    From $400 per night (USD)

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  • Palm Bay Club
    From $219 per night (USD)

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    Palm Bay Club

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    WELCOME Siesta Key Beach is the perfect spot for sunning, shelling, or taking a siesta. The Palm Bay Club is known for ...

    From $219 per night (USD)

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  • UNIT #209, Sea Shell Condos
    From $145 per night (USD)

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    UNIT #209, Sea Shell Condos

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    DIRECTLY ON CRESCENT BEACH! FREE TROLLEY UP AND DOWN THE KEY! BRAND NEW RECLINERS IN LIVING AREA. Condominium complex lo ...

    From $145 per night (USD)

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  • Only 150 yards to beautiful Crescent Beach and heated Pool!
    From $90 per night (USD)

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    Only 150 yards to beautiful Crescent Beach and heated Pool!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Newly updated Siesta Key villa just been upgraded with new kitchen, new vanities, newly painted and with the tiles steam ...

    From $90 per night (USD)

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  • Jamaica Royale #92
    From $100 per night (USD)

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    Jamaica Royale #92

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our garden view condo has two bedrooms with two baths and is located just steps from the white sand beaches of Siesta ...

    From $100 per night (USD)

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  • Tiny House - Green Lifeguard Stand
    From $85 per night (USD)

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    Tiny House - Green Lifeguard Stand

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Located just over the bridge from Siesta Key and minutes away from Sarasota's thriving dining and arts districts, our su ...

    From $85 per night (USD)

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  • 39 S. Polk Drive
    From $500 per night (USD)

    VRBO

    39 S. Polk Drive

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    PLEASE SEE CANCELLATION POLICIES BELOW - . Arrivals prior to 90 days are to be paid in full. Please note that the min ...

    From $500 per night (USD)

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    Details
  • 2/2 (342) Bayside T Model
    From $180 per night (USD)

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    2/2 (342) Bayside T Model

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This first floor 2-bedroom 2-bathroom condominium is located on the Bay side of our property. The Bay side has a pool, ...

    From $180 per night (USD)

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    Details
  • Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMERSPECIAL RATES!
    From $325 per night (USD)

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    Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMERSPECIAL RATES!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 BR, 2 BA, sleeps large family, heated pool-jacuzzi, free WIFI, across lake POOL AREA & LAKE-VIEW, KING BED, WOOD-FLOOR ...

    From $325 per night (USD)

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  • Amazing Villa
    From $145 per night (USD)

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    Amazing Villa

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    PLEASE NOTE: OUTDOOR SPA CANNOT BE HEATED AND OPERATES AT 84F! If you are looking for a luxurious and serene holiday in ...

    From $145 per night (USD)

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  • 2/2 (055) Tower Partial North View Ne
    From $260 per night (USD)

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    2/2 (055) Tower Partial North View Ne

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 55- 2 Bedrooms 2 Bathrooms Condominium With Partial Gulf Views Sleeps 6 | 2 bedroom, 2 bathroom partial North view ...

    From $260 per night (USD)

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  • The Little Sandy
    From $184 per night (USD)

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    The Little Sandy

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    You need a vacation and we've got just the place! Nestled amongst two ancient banyan trees, The Little Sandy rests on a ...

    From $184 per night (USD)

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  • 2 Bedroom Steps from Beach
    From $95 per night (USD)

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    2 Bedroom Steps from Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Amazing 1400 sq. ft unit in the quiet, well-maintained and desirable Village West in Siesta Key. Relax and enjoy the fin ...

    From $95 per night (USD)

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  • Bahia Vista Gulf
    From $93 per night (USD)

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    Bahia Vista Gulf

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Large Beachside Heated Pool - Situated ocean side our two bedroom, two bath condominiums are turnkey furnished and in ...

    From $93 per night (USD)

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  • Bay Oaks Condominium
    From $110 per night (USD)

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    Bay Oaks Condominium

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Perfect little condo on siesta key, home of the #1 rated beach in the USA. Just minutes from the beaches and great rest ...

    From $110 per night (USD)

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  • Ingram House
    From $150 per night (USD)

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    Ingram House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This 3 bedroom, 2 bathroom home is fully renovated, boasting a kitchen with a large island, large family room complete w ...

    From $150 per night (USD)

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  • Bay Tree Club; Gulf & Bay
    From $250 per night (USD)

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    Bay Tree Club; Gulf & Bay

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy all the beach & bay have to offer at this premium gulf front condominium on Siesta Key. The Bay Tree Club Condomin ...

    From $250 per night (USD)

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    Details
  • Excelsior Beach
    From $150 per night (USD)

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    Excelsior Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This lovely 2 bedroom, 2 bath condominium unit underwent a major top to bottom renovation. This is considered an A+ uni ...

    From $150 per night (USD)

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  • Home Away From Home in Tropical Paradise.
    From $100 per night (USD)

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    Home Away From Home in Tropical Paradise.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Recently updated and renovated 2 bedroom, 2 bath, first floor single story garden unit. Located in the beautiful Baypo ...

    From $100 per night (USD)

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    Details
  • The Pool House
    From $525 per night (USD)

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    The Pool House

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    16

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

    From $525 per night (USD)

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    Details
  • 1/1 (038) Tower Partial South Gulf View S
    From $190 per night (USD)

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    1/1 (038) Tower Partial South Gulf View S

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Beautifully Remodeled and Updated 1 Bedroom/1 Bathroom- Amazing View of the #1 Beach (Unit 38) | This one bedroom one ba ...

    From $190 per night (USD)

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    Details
  • Fisherman's Cove B109
    From $85 per night (USD)

    VRBO

    Fisherman's Cove B109

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy your home away from home in beautiful Siesta Key! This great 2-bedroom, 2-bath has everything you need for a wonde ...

    From $85 per night (USD)

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    Details
  • Only 150 yards to beautiful Siesta Key Beach and heated pool!
    From $90 per night (USD)

    VRBO

    Only 150 yards to beautiful Siesta Key Beach and heated pool!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Newly updated Siesta Key villa just been upgraded with new kitchen, new vanities, newly painted and with the tiles steam ...

    From $90 per night (USD)

    VRBO

    Details