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  • Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key
    From $321 per night (USD)

    VRBO

    Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta Key Located Next to Turtle Beach on ...

    From $321 per night (USD)

    VRBO

    Details
  • Nearly Beachfront, Gulf Views, Heated Pool & Pet-Friendly - Sugar Sand Cottage
    Click For Pricing

    Expedia

    Nearly Beachfront, Gulf Views, Heated Pool & Pet-Friendly - Sugar Sand Cottage

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    19

    Sugar Sand Cottage by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Siesta Key Luxury Rental Proper ...

    Click For Pricing

    Expedia

    Details
  • Downtown, Mins away from Lido Beach, Siesta Key, St Armands Cir
    From $141 per night (USD)

    VRBO

    Downtown, Mins away from Lido Beach, Siesta Key, St Armands Cir

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Rest and relax in this beautiful first-floor condo while being close to everything downtown Sarasota has to offer includ ...

    From $141 per night (USD)

    VRBO

    Details
  • Direct Siesta Key Beachfront condo!
    From $455 per night (USD)

    Expedia

    Direct Siesta Key Beachfront condo!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our beautiful fully remodeled condo is located directly across the street from world famous Siesta Key Beach! Whether yo ...

    From $455 per night (USD)

    Expedia

    Details
  • Clean Family Friendly 2 Bed, Private Beach Access, Renovated, GREAT LOCATION!
    From $356 per night (USD)

    VRBO

    Clean Family Friendly 2 Bed, Private Beach Access, Renovated, GREAT LOCATION!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to 9E at Sea Club II, our home away from home in the beach village of Siesta Key. Walk right in to our ground fl ...

    From $356 per night (USD)

    VRBO

    Details
  • Lake view spacious 2bdr CONDO 7 min by the BEACH
    From $148 per night (USD)

    Expedia

    Lake view spacious 2bdr CONDO 7 min by the BEACH

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This bright and cozy condo is very clean and feels like home, with amenities needed to stay a night, week or a month. T ...

    From $148 per night (USD)

    Expedia

    Details
  • One Bedroom - Ground Floor Condo - Heated Pool - Siesta Key Village
    From $214 per night (USD)

    VRBO

    One Bedroom - Ground Floor Condo - Heated Pool - Siesta Key Village

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated Pool Located right in the Heart of ...

    From $214 per night (USD)

    VRBO

    Details
  • Cozy Heated Pool Home, 3 bed 2 bath, 25 min beach
    From $184 per night (USD)

    Expedia

    Cozy Heated Pool Home, 3 bed 2 bath, 25 min beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This 3-bedroom villa offers screened solar heated recently resurfaced pool, fully fenced backyard, BBQ, Wi-Fi, 3 smart ...

    From $184 per night (USD)

    Expedia

    Details
  • Unit 401 Beautiful view of the Gulf of Mexico
    From $261 per night (USD)

    VRBO

    Unit 401 Beautiful view of the Gulf of Mexico

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Schedule your escape to Siesta Key Beach in the bright and clean Unit 401. This top floor, end unit has an open floor pl ...

    From $261 per night (USD)

    VRBO

    Details
  • Villa Fiesta  | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!
    From $342 per night (USD)

    Expedia

    Villa Fiesta | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Villa Fiesta, your ultimate island retreat nestled in the heart of Siesta Key Village. This stunning property ...

    From $342 per night (USD)

    Expedia

    Details
  • Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach!
    From $612 per night (USD)

    VRBO

    Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Welcome to Casa De Siesta, your ultimate island retreat nestled in the heart of Siesta Key Village. This stunning proper ...

    From $612 per night (USD)

    VRBO

    Details
  • Siesta Sunrise-Just steps to the beach and village
    From $555 per night (USD)

    Expedia

    Siesta Sunrise-Just steps to the beach and village

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Location, location, location! Siesta Sunrise is just steps to beautiful Siesta Key beach and a short walk to the village ...

    From $555 per night (USD)

    Expedia

    Details
  • Bright Coastal Condo: Walk to Lido Key Beach!
    From $283 per night (USD)

    VRBO

    Bright Coastal Condo: Walk to Lido Key Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    On Lido Key in Sarasota, this sunny beachside condo awaits. Boasting beautiful views of the ocean and a fully equipped k ...

    From $283 per night (USD)

    VRBO

    Details
  • Enjoy your stay
    From $203 per night (USD)

    Expedia

    Enjoy your stay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our house! It's located in a quiet neighbourhood in North Port FL - a fast growing community close to the sho ...

    From $203 per night (USD)

    Expedia

    Details
  • Myakka River
    From $250 per night (USD)

    VRBO

    Myakka River

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Bring your small boat or kayaks. Located in Venice near Wellen Park. This area is fisherman’s paradise. Tarpon, Redfish, ...

    From $250 per night (USD)

    VRBO

    Details
  • Beachfront Condo on Famous Siesta Key!
    From $540 per night (USD)

    Expedia

    Beachfront Condo on Famous Siesta Key!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Siesta Breakers, a beautiful beachfront 2 bedroom condo on Siesta Key 🏡 Property Highlights: ✨ Heated pool ...

    From $540 per night (USD)

    Expedia

    Details
  • The Alameda - Historic SRQ Getaways, Central SRQ
    From $224 per night (USD)

    VRBO

    The Alameda - Historic SRQ Getaways, Central SRQ

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The Space Welcome to the Indian Beach Sapphire Shores neighborhood of Sarasota, one of Sarasota's most desirable neighb ...

    From $224 per night (USD)

    VRBO

    Details
  • Gertrude's Siesta | 12-steps Beach Path, Free Bikes Paddleboards, 4-min to Village on Free Trolley!
    From $396 per night (USD)

    Expedia

    Gertrude's Siesta | 12-steps Beach Path, Free Bikes Paddleboards, 4-min to Village on Free Trolley!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The Oceanside 603 Large king apartment perfectly located. 12-steps to Siesta Key's best beach access! 3-min by trolley ...

    From $396 per night (USD)

    Expedia

    Details
  • Sun, Sand and Savings Sarasota Deals Up to 15% Off
    From $230 per night (USD)

    VRBO

    Sun, Sand and Savings Sarasota Deals Up to 15% Off

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Looking for a great deal? Discounts are automatically applied based on your length of stay! No need for promo codes or r ...

    From $230 per night (USD)

    VRBO

    Details
  • Crystal Sands Villa 12A
    From $411 per night (USD)

    Expedia

    Crystal Sands Villa 12A

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    One of a kind at Crystal Sands just steps from one of our two heated pools and only 100 yards from the white sand of Cre ...

    From $411 per night (USD)

    Expedia

    Details
  • Entire private house
    From $525 per night (USD)

    VRBO

    Entire private house

    Bedrooms:
    1
    Bathrooms:
    5
    Sleeps:
    10

    Enjoy Full master suite with Jacuzzi tub w/private access to pool with built in hot tub.There are 4 more bedrooms throug ...

    From $525 per night (USD)

    VRBO

    Details
  • Stand alone villa
    From $234 per night (USD)

    Expedia

    Stand alone villa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Stand alone villa with private patio and garden, just steps to the pool and beach. Putting green and shuffle board. Qui ...

    From $234 per night (USD)

    Expedia

    Details
  • Penthouse timeshare
    Click For Pricing

    VRBO

    Penthouse timeshare

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    A rare opportunity to escape to your four bedroom penthouse on the beach in Longboat Key or for a week in February (2/5/ ...

    Click For Pricing

    VRBO

    Details
  •   Walk to beach   Heated POOL   King bed  DAILY  WEEKLY    Villa 4    SPECIALS
    From $520 per night (USD)

    Expedia

    Walk to beach Heated POOL King bed DAILY WEEKLY Villa 4 SPECIALS

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    We are a small resort on Siesta Key offering daily rentals Enjoy Siesta Key in style! Brand new high end ground floor lu ...

    From $520 per night (USD)

    Expedia

    Details
  • Veranda Beach Club, beachfront Longboat Key, Florida
    Click For Pricing

    VRBO

    Veranda Beach Club, beachfront Longboat Key, Florida

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit #309, a beach front condo, is available Weeks #51 & #52 2019, and Week #1 2020. Unit #306, with a partial ocean vi ...

    Click For Pricing

    VRBO

    Details
  • Pool ❤ Home - Close to Beaches, Food, Downtown, Parks, St. Armand's, etc
    From $306 per night (USD)

    Expedia

    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 $306 per night (USD)

    Expedia

    Details
  • *NEW LISTING* Incredible Lake View!
    From $161 per night (USD)

    VRBO

    *NEW LISTING* Incredible Lake View!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Looking for the perfect get-away location? Welcome to Serenata, one of Sarasota’s most sought after resort communities i ...

    From $161 per night (USD)

    VRBO

    Details
  • The Sun Dial | Waterfront Home on Siesta Key w/ Private Pool & Large Backyard, Close to Beach!
    Click For Pricing

    Expedia

    The Sun Dial | Waterfront Home on Siesta Key w/ Private Pool & Large Backyard, Close to Beach!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Step inside this magnificent Siesta Key rental home and discover a world of luxury and tranquility. Nestled on the water ...

    Click For Pricing

    Expedia

    Details
  • Sarasota-Indian Beach Zen Home (private-pet friendly)
    From $192 per night (USD)

    VRBO

    Sarasota-Indian Beach Zen Home (private-pet friendly)

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    You’ll love this private home, centrally located to everything when you stay at this zen space 2 blocks to the local bay ...

    From $192 per night (USD)

    VRBO

    Details
  • 🌴Tropical Retreat in Sarasota
    From $323 per night (USD)

    Expedia

    🌴Tropical Retreat in Sarasota

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    This completely renovated home with full kitchen 3 bedrooms 2 bath split plan has a large Florida room with a attached s ...

    From $323 per night (USD)

    Expedia

    Details
  • Beautiful Coastal Home located within 2 miles to the beach!!
    From $367 per night (USD)

    VRBO

    Beautiful Coastal Home located within 2 miles to the beach!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Located ONLY 2 MILES FROM MANASOTA BEACH this fully furnished adorable beach themed place is available for you to come a ...

    From $367 per night (USD)

    VRBO

    Details
  • Pure Beachfront! Exceeds expectations! Private stairs to pool & beach. 2 decks!
    From $864 per night (USD)

    Expedia

    Pure Beachfront! Exceeds expectations! Private stairs to pool & beach. 2 decks!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    You want a perfect location. You want a clean, fresh vacation rental with quality furnishings. You want more - not less ...

    From $864 per night (USD)

    Expedia

    Details
  • Siesta Key beach house
    From $687 per night (USD)

    VRBO

    Siesta Key beach house

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Nice house as is renovated to January-2025 and there is new kitchen , bathroom, furniture and beds and private pool with ...

    From $687 per night (USD)

    VRBO

    Details
  • Beachside Retreat with Pool and Beach Access
    Click For Pricing

    Expedia

    Beachside Retreat with Pool and Beach Access

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Service Highlights: - Professionally laundered linens & towels with each reservation. - Exceptional clean rating. - No k ...

    Click For Pricing

    Expedia

    Details
  • Massive Mediterranean Beachside Bliss
    From $1764 per night (USD)

    VRBO

    Massive Mediterranean Beachside Bliss

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    18

    Across the street from the #1 Beach, two fabulous 3 bedroom, 3 bath townhomes with a shared pool and in unit elevator th ...

    From $1764 per night (USD)

    VRBO

    Details
  • The Beachside Retreat you have been looking for
    From $453 per night (USD)

    Expedia

    The Beachside Retreat you have been looking for

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Service Highlights: - Professionally laundered linens & towels with each reservation. - Exceptional clean rating. - No k ...

    From $453 per night (USD)

    Expedia

    Details
  • Margaritaville - Pool ❤ w/ Hot Tub, Close to Beaches, Restaurants, Shopping +++
    Click For Pricing

    VRBO

    Margaritaville - Pool ❤ w/ Hot Tub, Close to Beaches, Restaurants, Shopping +++

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    8

    Phenomenal, 4/2, 1894 sf home with all the amenities: Huge heated pool, Smart TVs in every room, Large kitchen with Isla ...

    Click For Pricing

    VRBO

    Details
  • AMAZING 3 bedroom -15 miles from Venice beach.
    From $168 per night (USD)

    Expedia

    AMAZING 3 bedroom -15 miles from Venice beach.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Amazing 3 bedroom, great for a couple looking to get away for a month or two to the Beautiful West Coast of Florida. Stu ...

    From $168 per night (USD)

    Expedia

    Details
  • Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
    From $234 per night (USD)

    VRBO

    Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come enjoy this adorable 2-Bedroom, 2-Bathroom centrally located Siesta Key Condo with large heated pool! The condo is a ...

    From $234 per night (USD)

    VRBO

    Details
  • Get To the Beach!  Only 5 miles to Siesta Key Beach!
    From $150 per night (USD)

    Expedia

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

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $150 per night (USD)

    Expedia

    Details
  • Beautiful Getaway ~ 4 Miles to Venice Beach!
    From $280 per night (USD)

    VRBO

    Beautiful Getaway ~ 4 Miles to Venice Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Florida is a beautiful state with amazing beaches and this 3-bedroom, 2.5-bath vacation rental gives you access to the b ...

    From $280 per night (USD)

    VRBO

    Details
  • Discounted rates for gorgeous one bdrm directly across from beach, near village!
    From $269 per night (USD)

    Expedia

    Discounted rates for gorgeous one bdrm directly across from beach, near village!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Gorgeous updated, just renovated, newly furnished one bedroom! Best location on Siesta beach and a short walk to charmi ...

    From $269 per night (USD)

    Expedia

    Details
  • Siesta Key Waterfront Condo on Turtle Beach Inlet. Fish, Swim & Boat just Steps from Your Door.  The
    From $133 per night (USD)

    VRBO

    Siesta Key Waterfront Condo on Turtle Beach Inlet. Fish, Swim & Boat just Steps from Your Door. The

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Perfect location to relax and enjoy your tropical vacation or get away from the cold northern winters. Comfortable 2 bed ...

    From $133 per night (USD)

    VRBO

    Details
  • Quiet, Cozy, Bungalow with a Pool. Near Venice Beach and Warm Mineral Springs
    Click For Pricing

    Expedia

    Quiet, Cozy, Bungalow with a Pool. Near Venice Beach and Warm Mineral Springs

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Open floor plan, 3 bedroom home with a breakfast bar and spacious living room that opens to a large screened in, in grou ...

    Click For Pricing

    Expedia

    Details
  • GEORGEOUS HOME ONLY 3MILES AWAY FROM NOKOMIS BEACH
    From $161 per night (USD)

    VRBO

    GEORGEOUS HOME ONLY 3MILES AWAY FROM NOKOMIS BEACH

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Gorgeous lake view, newer 3 bedroom, 2 bath, plus den home with community pool/gated. Thoughtfully appointed with all of ...

    From $161 per night (USD)

    VRBO

    Details
  • Crystal Sands Tower Unit 602 - Beachfront
    From $426 per night (USD)

    Expedia

    Crystal Sands Tower Unit 602 - Beachfront

    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 $426 per night (USD)

    Expedia

    Details
  • Relax at Private Sandy Beach Aqua Pool House with FREE Bikes & Kayaks for Two!
    From $397 per night (USD)

    VRBO

    Relax at Private Sandy Beach Aqua Pool House with FREE Bikes & Kayaks for Two!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to our family vacation home in Venice Florida. This is one of our homes away from home and we enjoy sharing it ...

    From $397 per night (USD)

    VRBO

    Details
  • Modern 2 Bedroom House Near Siesta Key
    Click For Pricing

    Expedia

    Modern 2 Bedroom House Near Siesta Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our home is fully renovated with nearly brand new furniture. With 2 bedrooms, 2 bathrooms, and 3 beds total, we can comf ...

    Click For Pricing

    Expedia

    Details
  • Tiny House Pelican - sleeps 2
    Click For Pricing

    VRBO

    Tiny House Pelican - sleeps 2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Amy was the first house to arrive at Tiny House Siesta. She is one of our smallest as she comfortably sleeps 3 ...

    Click For Pricing

    VRBO

    Details
  • Aqua Oasis- Tiny House sleeps 6 & Pet friendly
    From $188 per night (USD)

    Expedia

    Aqua Oasis- Tiny House sleeps 6 & Pet friendly

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Summary: This tiny home offers three bedrooms. From the living room, two stair cases lead you to opposite sides of the ...

    From $188 per night (USD)

    Expedia

    Details
  • Tiny House Yellow Lifeguard Stand- pet friendly
    From $194 per night (USD)

    VRBO

    Tiny House Yellow Lifeguard Stand- pet friendly

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Summary: Located just over the bridge from Siesta Key and minutes away from Sarasota’s thriving dining and arts district ...

    From $194 per night (USD)

    VRBO

    Details
  • Tiny House Sand Dollar near Siesta Key
    From $197 per night (USD)

    Expedia

    Tiny House Sand Dollar near Siesta Key

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Experience compact living in Tiny House Sand dollar. Roughly 350 sq feet and designed for simplicity and effici ...

    From $197 per night (USD)

    Expedia

    Details
  • Delightful Pool House 3 Miles to Siesta Key Beaches
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    VRBO

    Delightful Pool House 3 Miles to Siesta Key Beaches

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Our private pool home is fully set up with brand new furniture. With 3 bedrooms, 2 bathrooms, and 4 total beds, we can c ...

    Click For Pricing

    VRBO

    Details
  • Tiny House Piña Colada- pet friendly
    From $311 per night (USD)

    Expedia

    Tiny House Piña Colada- pet friendly

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Summary: This Tiny House was built by Tumbleweed. Once you walk thru the door, you know you are at the beach. Eleanor ha ...

    From $311 per night (USD)

    Expedia

    Details
  • Tiny Coral Oasis-  beachy tiny house for your getaway
    From $222 per night (USD)

    VRBO

    Tiny Coral Oasis- beachy tiny house for your getaway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: It will be love at first sight with our tiny Blue Oasis Cool off inside where the bleached white wood brightens ...

    From $222 per night (USD)

    VRBO

    Details
  • El Presidente Condos unit 507, Top Floor With Gulf Views directly on the beach!
    From $388 per night (USD)

    Expedia

    El Presidente Condos unit 507, Top Floor With Gulf Views directly on the beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Recently renovated to include open concept living with a brand new Gourmet Kitchen and island. Granite counter tops, ...

    From $388 per night (USD)

    Expedia

    Details
  • Red Lifeguard Stand - pet freindly
    From $193 per night (USD)

    VRBO

    Red Lifeguard Stand - pet freindly

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Located just over the bridge from Siesta Key and minutes away from Sarasota’s thriving dining and arts district ...

    From $193 per night (USD)

    VRBO

    Details
  • Perfect home away, modern amenities, ~ Heated Pool ~ Close to S. Venice Beach
    From $273 per night (USD)

    Expedia

    Perfect home away, modern amenities, ~ Heated Pool ~ Close to S. Venice Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come and enjoy our Lemon Tree House! Virtual Tour: https://www.youtube.com/embed/Y68OcyA9tv8?rel=0.  Escape to your ...

    From $273 per night (USD)

    Expedia

    Details
  • Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool
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    VRBO

    Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and roll-a-ways available on ...

    Click For Pricing

    VRBO

    Details
  • Beachfront Sarasota Resort Condo: Siesta Key View!
    From $217 per night (USD)

    Expedia

    Beachfront Sarasota Resort Condo: Siesta Key View!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sink your toes into Siesta Key's white sand beaches and swim in the crystal clear waters of the Gulf of Mexico during yo ...

    From $217 per night (USD)

    Expedia

    Details
  • Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key
    From $214 per night (USD)

    VRBO

    Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The Siesta Heron Suites & Villas enjoys a proximity that is close to the heart of everything that makes Siesta Key speci ...

    From $214 per night (USD)

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  • Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks
    From $241 per night (USD)

    Expedia

    Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The last of our Siesta Heron escapes offers something extra the others don't and that is an extra bedroom. Key Lime, the ...

    From $241 per night (USD)

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    Details
  • 1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool
    From $188 per night (USD)

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    1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located ...

    From $188 per night (USD)

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  • Spacious vacation rental condo with lagoon views, beach access, and pool
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    Expedia

    Spacious vacation rental condo with lagoon views, beach access, and pool

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    When you're overdue for a refreshing vacation, a trip to Siesta Key is always a good idea. Making the experience even mo ...

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  • Sarasota House w/ Private Pool - 4 Mi to Beach!
    From $263 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 $263 per night (USD)

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  • Sleeps 2. Mins to Downtown, Beaches & Airport / Ground Floor Unit
    From $86 per night (USD)

    Expedia

    Sleeps 2. Mins to Downtown, Beaches & Airport / Ground Floor Unit

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Ground floor unit (No Stairs). Sleeps two (2). Renting this unit will place you within walking distance of Sarasota’s do ...

    From $86 per night (USD)

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  • Vacation Rental on Siesta Key
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    Vacation Rental on Siesta Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to this modern and spacious tropical getaway. This newly renovated two bedroom, two bathroom, and den Condo is l ...

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  • Panoramic water view 3br  pool home
    From $225 per night (USD)

    Expedia

    Panoramic water view 3br pool home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Relax and enjoy the panoramic waterfront views of the Miakahatchi river waterway from our deck or inground pool off a Ti ...

    From $225 per night (USD)

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  • Dog-Friendly Home w/ Yard ~ 6 Miles to the Beach!
    From $102 per night (USD)

    VRBO

    Dog-Friendly Home w/ Yard ~ 6 Miles to the Beach!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Get away to the Gulf Coast and stay at this Sarasota vacation rental! The 3-bedroom, 1-bathroom home features a spacious ...

    From $102 per night (USD)

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  • Sunny Apartments a block from Warm Mineral Springs
    From $64 per night (USD)

    Expedia

    Sunny Apartments a block from Warm Mineral Springs

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Sunny apartments! Very clean and recently updated property a block away from world famous Warm Mineral Spri ...

    From $64 per night (USD)

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  • Sun, Sand and Savings Sarasota Deals Up to 15% Off
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    VRBO

    Sun, Sand and Savings Sarasota Deals Up to 15% Off

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Looking for a great deal? Discounts are automatically applied based on your length of stay! No need for promo codes or r ...

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  • Al'Most Heaven
    From $296 per night (USD)

    Expedia

    Al'Most Heaven

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful Old Town nice backyard three bedroom two bath all new furniture 3 miles to Beach convenient to all restaurants ...

    From $296 per night (USD)

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  • Beach apartment…Sun ,air , water -best friends
    From $130 per night (USD)

    VRBO

    Beach apartment…Sun ,air , water -best friends

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    11:02 1 Beach life in this renovated seaside condo overlooking the Gulf of Mexico from your veranda. there is a heated ...

    From $130 per night (USD)

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    Details
  • Sun, Sand and Savings Sarasota Deals Up to 15% Off
    From $227 per night (USD)

    Expedia

    Sun, Sand and Savings Sarasota Deals Up to 15% Off

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Looking for a great deal? Discounts are automatically applied based on your length of stay! No need for promo codes or r ...

    From $227 per night (USD)

    Expedia

    Details
  • Beachfront Condo - Across from Siesta Beach
    From $335 per night (USD)

    VRBO

    Beachfront Condo - Across from Siesta Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located directly across from world-renowned Siesta Key Beach, this fabulous condo is the perfect vacation retreat with a ...

    From $335 per night (USD)

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    Details
  • Steps to the Gulf & Amazing View - A103, WiFi & Boat Docks
    From $302 per night (USD)

    Expedia

    Steps to the Gulf & Amazing View - A103, WiFi & Boat Docks

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Gulf of Mexico is only 100 ft. from your private sand beach and lanai entrance. Listen to the surf also from your ma ...

    From $302 per night (USD)

    Expedia

    Details
  • POOL VIEW  Walk to beach  King bed  Heated pool   DAILY  WEEKLY SPECIAL
    From $520 per night (USD)

    VRBO

    POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    We are a small resort on Siesta Key offering daily rentals Luxury 1 bedroom villa on Siesta Key. Easy 5 minute walk to ...

    From $520 per night (USD)

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    Details
  • Venice charm on the Island with a Pool 55+ bungalow
    From $225 per night (USD)

    Expedia

    Venice charm on the Island with a Pool 55+ bungalow

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    In the heart of Venice, Florida, you can find our single level, cozy 2-bedroom villa . Nestled just a 15 minute walk fro ...

    From $225 per night (USD)

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    Details
  • Upscale Vacation House in South Venice
    From $198 per night (USD)

    VRBO

    Upscale Vacation House in South Venice

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Upscale modern luxury South Venice house 3 bedrooms, 2 baths, 2000 sf, high ceiling, modern Italian furniture. 10 min sh ...

    From $198 per night (USD)

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  • Beach Front Condo, Venice, Florida. 2 bedroom, 2 bath, heated pool.
    Click For Pricing

    Expedia

    Beach Front Condo, Venice, Florida. 2 bedroom, 2 bath, heated pool.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Totally renovated 2 bed and 2 bath condo on private beach, 1/2 mile to down town Venice and short walk to the Venice j ...

    Click For Pricing

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  • JULY 4TH WEEK AVAILABLE! PROPERTY RIGHT ON THE BEACH! BOOK NOW!
    From $348 per night (USD)

    VRBO

    JULY 4TH WEEK AVAILABLE! PROPERTY RIGHT ON THE BEACH! BOOK NOW!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come to Siesta Key, with its beaches and sunsets as beautiful as ever. All shops restaurants and bars are popping! Sie ...

    From $348 per night (USD)

    VRBO

    Details
  • Location, Location!  Sarasota Rambler | Downtown MidMod Stay
    From $203 per night (USD)

    Expedia

    Location, Location! Sarasota Rambler | Downtown MidMod Stay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Our recently updated 1200 square foot mid-century rambler home is located in the charming downtown Sarasota neighborhood ...

    From $203 per night (USD)

    Expedia

    Details
  • Beautiful Gulf View on Siesta Key
    From $236 per night (USD)

    VRBO

    Beautiful Gulf View on Siesta Key

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This Two Bedroom, One Bath condo is just steps to the white, powdered sugar sand of Siesta Key. Here at La Siesta Condom ...

    From $236 per night (USD)

    VRBO

    Details
  • Siesta Key Designer Home: *Pool, Gardens, Luxury*
    From $937 per night (USD)

    Expedia

    Siesta Key Designer Home: *Pool, Gardens, Luxury*

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Get lost in the intoxicating relaxation of Siesta Key, in this luxurious private home with a pool. This tropical retrea ...

    From $937 per night (USD)

    Expedia

    Details
  • Retreat Between the Beach & Bay
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    VRBO

    Retreat Between the Beach & Bay

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    The quaintness of our condo and its location are unmatched. This 2B/2B unit is steps away from the bay, and merely acros ...

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    Details
  • Super Clean!  Minutes to Siesta Key.
    From $213 per night (USD)

    Expedia

    Super Clean! Minutes to Siesta Key.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This 2 bedroom, 2 bathroom, ground-floor condo has been completely redone with your comfort in mind. All new furnishings ...

    From $213 per night (USD)

    Expedia

    Details
  • Crystal Sands Tower Unit 508 - Beachfront
    From $457 per night (USD)

    VRBO

    Crystal Sands Tower Unit 508 - Beachfront

    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 $457 per night (USD)

    VRBO

    Details
  • Crystal Sands Tower Unit 605 - Beachfront
    From $432 per night (USD)

    Expedia

    Crystal Sands Tower Unit 605 - Beachfront

    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 $432 per night (USD)

    Expedia

    Details
  • Crystal Sands Villa 15 - Private Beach
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    Crystal Sands Villa 15 - Private Beach

    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 ...

    Click For Pricing

    VRBO

    Details
  • Newly Remodeled Open Concept Home with Pool in the heart of Siesta Key
    From $559 per night (USD)

    Expedia

    Newly Remodeled Open Concept Home with Pool in the heart of Siesta Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    HURRICANE UPDATE: HOME STAYED DRY! NO WATER INFILTRATION OR DAMAGE FROM HURRICANES! NEW NEW!! UPDATED PHOTOS COMING SOO ...

    From $559 per night (USD)

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    Details
  • Updated Sienna Park Condo - 4 Miles to Siesta Key!
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    VRBO

    Updated Sienna Park Condo - 4 Miles to Siesta Key!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Book this renovated 3-bed, 2-bath vacation rental for your next visit to Sarasota! Nestled in the heart of Southern Sara ...

    Click For Pricing

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    Details
  • St. Armand's Canal-Front Pool Home
    From $1223 per night (USD)

    Expedia

    St. Armand's Canal-Front Pool Home

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    St. Armand's Canal-Front Pool Home steps to the beach! This gem of an estate has been completely rebuilt and remodeled. ...

    From $1223 per night (USD)

    Expedia

    Details
  • Crystal Sands Unit 806 - Beachfront
    From $550 per night (USD)

    VRBO

    Crystal Sands Unit 806 - Beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unbelievable Beach Views - Just Walk Downstairs to Your White Sand Paradise Enjoy a view of world famous Siesta Key th ...

    From $550 per night (USD)

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    Details
  • Crystal Sands Villa 13 - Private Beach
    From $400 per night (USD)

    Expedia

    Crystal Sands Villa 13 - Private Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    For more privacy we offer you this 2 bedroom 2 bath villa flanking our attractive palm lined boulevard and steps from ou ...

    From $400 per night (USD)

    Expedia

    Details
  • Crystal Sands Tower Unit 203 - Beachfront
    From $432 per night (USD)

    VRBO

    Crystal Sands Tower Unit 203 - Beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    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 $432 per night (USD)

    VRBO

    Details
  • Crystal Sands Tower Unit 805 - Beachfront
    From $457 per night (USD)

    Expedia

    Crystal Sands Tower Unit 805 - Beachfront

    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 $457 per night (USD)

    Expedia

    Details
  • Crystal Sands Villa 17 - Private Beach
    From $400 per night (USD)

    VRBO

    Crystal Sands Villa 17 - Private Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    For more privacy we offer you this 2 bedroom 2 bath villa flanking our attractive palm lined boulevard. Gracious living ...

    From $400 per night (USD)

    VRBO

    Details
  • Crystal Sands Tower Unit 307 - Beachfront
    From $454 per night (USD)

    Expedia

    Crystal Sands Tower Unit 307 - Beachfront

    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 $454 per night (USD)

    Expedia

    Details
  • 2 Bedroom 1 Bath condo is steps to the white powdered  sand of Siesta Key
    From $241 per night (USD)

    VRBO

    2 Bedroom 1 Bath condo is steps to the white powdered sand of Siesta Key

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Her at La Siesta Condominiums you also have easy access to Siesta Village and it's numerous restaurants, specialty shops ...

    From $241 per night (USD)

    VRBO

    Details
  • Crystal Sands Tower Unit 1204 - Beachfront
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    Expedia

    Crystal Sands Tower Unit 1204 - Beachfront

    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 ...

    Click For Pricing

    Expedia

    Details