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  • Myakka River
    From $442 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 $442 per night (USD)

    VRBO

    Details
  • Beachfront Condo on Famous Siesta Key!
    From $544 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 $544 per night (USD)

    Expedia

    Details
  • Retro-Chic 2BR Bungalow in Sarasota Historic Neighborhood, Firepit, near Bay
    From $286 per night (USD)

    VRBO

    Retro-Chic 2BR Bungalow in Sarasota Historic Neighborhood, Firepit, near Bay

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to the Indian Beach Sapphire Shores neighborhood of Sarasota, one of Sarasota's most desirable neighborhoods. T ...

    From $286 per night (USD)

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    Details
  • Gertrude's Siesta | 1 min walk to Beach Path | Free Bikes, Boards & Trolley!
    From $493 per night (USD)

    Expedia

    Gertrude's Siesta | 1 min walk to Beach Path | Free Bikes, Boards & 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 $493 per night (USD)

    Expedia

    Details
  • Condo on Quiet Cul-De-Sac | Heated Pool/Spa | Tennis | Putting Green | Short Drive to Beach
    From $213 per night (USD)

    VRBO

    Condo on Quiet Cul-De-Sac | Heated Pool/Spa | Tennis | Putting Green | Short Drive to Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...

    From $213 per night (USD)

    VRBO

    Details
  • Crystal Sands Villa 12A
    From $460 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 $460 per night (USD)

    Expedia

    Details
  • Entire private house
    From $420 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 $420 per night (USD)

    VRBO

    Details
  • The Flamingo House at Indian Beach Sapphire Shores
    From $167 per night (USD)

    VRBO

    The Flamingo House at Indian Beach Sapphire Shores

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Enjoy your stay in Sarasota at this charming "Old Florida" West of Trail home with fenced yard, minutes to downtown, att ...

    From $167 per night (USD)

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    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

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    Details
  •   Walk to beach   Heated POOL   King bed  DAILY  WEEKLY    Villa 4    SPECIALS
    From $221 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 $221 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

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    Details
  • Pool ❤ Home - Close to Beaches, Food, Downtown, Parks, St. Armand's, etc
    From $317 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 $317 per night (USD)

    Expedia

    Details
  • The Sun Dial | Waterfront Home on Siesta Key w/ Private Pool & Large Backyard, Close to Beach!
    From $882 per night (USD)

    VRBO

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

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    🌴 The Sun Dial | Waterfront Pool Home + Walk to Beach 💖 Why You'll Love This Home Nestled on the peaceful canals of S ...

    From $882 per night (USD)

    VRBO

    Details
  • Sarasota-Indian Beach Zen Home (private-pet friendly)
    From $177 per night (USD)

    Expedia

    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 $177 per night (USD)

    Expedia

    Details
  • 🌴Tropical Retreat in Sarasota
    From $260 per night (USD)

    VRBO

    🌴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 $260 per night (USD)

    VRBO

    Details
  • Beautiful Coastal Home located within 2 miles to the beach!!
    From $255 per night (USD)

    Expedia

    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 $255 per night (USD)

    Expedia

    Details
  • Pure Beachfront! Exceeds expectations! Private stairs to pool & beach. 2 decks!
    From $834 per night (USD)

    VRBO

    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 $834 per night (USD)

    VRBO

    Details
  • Waterfront Beach House- Pool - Kayaks - Boat Ramp
    From $315 per night (USD)

    Expedia

    Waterfront Beach House- Pool - Kayaks - Boat Ramp

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This unique 2 bed / 2 bath Old Florida home features over 150 feet of private waterfront—perfect for those seeking peace ...

    From $315 per night (USD)

    Expedia

    Details
  • Siesta Key beach house
    From $904 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 $904 per night (USD)

    VRBO

    Details
  • Beachside Retreat with Pool and Beach Access
    From $567 per night (USD)

    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 ...

    From $567 per night (USD)

    Expedia

    Details
  • Massive Mediterranean Beachside Bliss
    From $1526 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 $1526 per night (USD)

    VRBO

    Details
  • The Beachside Retreat you have been looking for
    From $610 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 $610 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 $147 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 $147 per night (USD)

    Expedia

    Details
  • Beautiful Getaway ~ 4 Miles to Venice Beach!
    From $317 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 $317 per night (USD)

    VRBO

    Details
  • Discounted rates for gorgeous one bdrm directly across from beach, near village!
    From $262 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 $262 per night (USD)

    Expedia

    Details
  • Siesta Key Waterfront Condo on Turtle Beach Inlet. Fish, Swim & Boat just Steps from Your Door.  The
    From $140 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 $140 per night (USD)

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • Crystal Sands Tower Unit 602 - Beachfront
    From $454 per night (USD)

    VRBO

    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 $454 per night (USD)

    VRBO

    Details
  • Relax at Private Sandy Beach Aqua Pool House with FREE Bikes & Kayaks for Two!
    From $342 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 $342 per night (USD)

    VRBO

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

    VRBO

    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

    VRBO

    Details
  • Tiny House Pelican - sleeps 2
    From $202 per night (USD)

    Expedia

    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 ...

    From $202 per night (USD)

    Expedia

    Details
  • Aqua Oasis- Tiny House sleeps 4 & Pet friendly
    From $191 per night (USD)

    VRBO

    Aqua Oasis- Tiny House sleeps 4 & Pet friendly

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

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

    From $191 per night (USD)

    VRBO

    Details
  • Tiny House Yellow Lifeguard Stand- pet friendly
    From $206 per night (USD)

    Expedia

    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 $206 per night (USD)

    Expedia

    Details
  • Tiny House Sand Dollar near Siesta Key
    From $195 per night (USD)

    VRBO

    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 $195 per night (USD)

    VRBO

    Details
  • Delightful Pool House 3 Miles to Siesta Key Beaches
    Click For Pricing

    Expedia

    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

    Expedia

    Details
  • Tiny House Piña Colada- pet friendly
    From $220 per night (USD)

    VRBO

    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 $220 per night (USD)

    VRBO

    Details
  • Tiny Coral Oasis-  beachy tiny house for your getaway
    From $202 per night (USD)

    Expedia

    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 $202 per night (USD)

    Expedia

    Details
  • Red Lifeguard Stand - pet freindly
    From $196 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 $196 per night (USD)

    VRBO

    Details
  • Perfect home away, modern amenities, ~ Heated Pool ~ Close to S. Venice Beach
    From $282 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 $282 per night (USD)

    Expedia

    Details
  • Lakefront Property on Siesta Key Among Tropical Landscape W/ Heated Pool
    From $232 per night (USD)

    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 ...

    From $232 per night (USD)

    VRBO

    Details
  • Beachfront Sarasota Resort Condo: Siesta Key View!
    From $211 per night (USD)

    VRBO

    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 $211 per night (USD)

    VRBO

    Details
  • Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key
    From $234 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 $234 per night (USD)

    VRBO

    Details
  • Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks
    From $284 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 $284 per night (USD)

    Expedia

    Details
  • 1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool
    From $227 per night (USD)

    VRBO

    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 $227 per night (USD)

    VRBO

    Details
  • Spacious vacation rental condo with lagoon views, beach access, and pool
    From $276 per night (USD)

    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 ...

    From $276 per night (USD)

    Expedia

    Details
  • Sleeps 2. Mins to Downtown, Beaches & Airport / Ground Floor Unit
    From $90 per night (USD)

    VRBO

    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 $90 per night (USD)

    VRBO

    Details
  • Vacation Rental on Siesta Key
    From $362 per night (USD)

    Expedia

    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 ...

    From $362 per night (USD)

    Expedia

    Details
  • Dog-Friendly Home w/ Yard ~ 6 Miles to the Beach!
    From $140 per night (USD)

    VRBO

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

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

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

    From $140 per night (USD)

    VRBO

    Details
  • Sunny Apartments a block from Warm Mineral Springs
    From $71 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 $71 per night (USD)

    Expedia

    Details
  • Simply Paradise! Updated Corner Unit Steps to Lido Beach & St. Armand's Circle, Pool, & Spa!
    From $371 per night (USD)

    VRBO

    Simply Paradise! Updated Corner Unit Steps to Lido Beach & St. Armand's Circle, Pool, & Spa!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...

    From $371 per night (USD)

    VRBO

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

    VRBO

    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)

    VRBO

    Details
  • Beach apartment…Sun ,air , water -best friends
    From $158 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 $158 per night (USD)

    VRBO

    Details
  • Expansive Renovated Condo, Heated Pools, Tennis, Fishing on Intracoastal | Siesta Key Beach
    From $218 per night (USD)

    Expedia

    Expansive Renovated Condo, Heated Pools, Tennis, Fishing on Intracoastal | Siesta Key Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...

    From $218 per night (USD)

    Expedia

    Details
  • Beachfront Condo - Across from Siesta Beach
    From $343 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 $343 per night (USD)

    VRBO

    Details
  • Steps to the Gulf & Amazing View - A103, WiFi & Boat Docks
    From $363 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 $363 per night (USD)

    Expedia

    Details
  • POOL VIEW  Walk to beach  King bed  Pool Daily Rentals
    From $235 per night (USD)

    VRBO

    POOL VIEW Walk to beach King bed Pool Daily Rentals

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $235 per night (USD)

    VRBO

    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)

    Expedia

    Details
  • Upscale Vacation House in South Venice
    From $153 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 $153 per night (USD)

    VRBO

    Details
  • Beach Front Condo, Venice, Florida. 2 bedroom, 2 bath, heated pool.
    From $156 per night (USD)

    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 ...

    From $156 per night (USD)

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    Details
  • Beachfront Bliss, Siesta Key – Reno'd 2BR/2BA Condo w/Pool & Direct Beach Access
    From $328 per night (USD)

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    Beachfront Bliss, Siesta Key – Reno'd 2BR/2BA Condo w/Pool & Direct Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to a slice of paradise — a fully renovated 2-bedroom, 2-bath condo located directly on Siesta Key’s Crescent Bea ...

    From $328 per night (USD)

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    Details
  • Location, Location!  Sarasota Rambler Downtown MidMod Stay
    From $215 per night (USD)

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    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 $215 per night (USD)

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  • Condo# 404 Beautiful Gulf View on Siesta Key
    From $274 per night (USD)

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    Condo# 404 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 $274 per night (USD)

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    Details
  • Siesta Key Designer Home: *Pool, Gardens, Luxury*
    From $1121 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 $1121 per night (USD)

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  • Retreat Between the Beach & Bay
    From $290 per night (USD)

    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 ...

    From $290 per night (USD)

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    Details
  • JANUARY SPECIAL: Under $5,000! Minutes to Siesta Key.
    From $231 per night (USD)

    Expedia

    JANUARY SPECIAL: Under $5,000! 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 $231 per night (USD)

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    Details
  • Crystal Sands Tower Unit 508 - Beachfront
    From $608 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 $608 per night (USD)

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    Details
  • Crystal Sands Tower Unit 605 - Beachfront
    From $473 per night (USD)

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    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 $473 per night (USD)

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  • Crystal Sands Villa 15 - Private Beach
    From $436 per night (USD)

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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 ...

    From $436 per night (USD)

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    Details
  • Newly Remodeled Open Concept Home with Pool in the heart of Siesta Key
    From $303 per night (USD)

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    MODERN COASTAL meets funky boho at Chasin' Waves, a NEWLY REMODELED, OPEN CONCEPT home nestled on one of Siesta Key's mo ...

    From $303 per night (USD)

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  • Updated Sienna Park Condo - 4 Miles to Siesta Key!
    From $269 per night (USD)

    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 ...

    From $269 per night (USD)

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  • Precise Realty presents The Canal Breeze Retreat
    From $1404 per night (USD)

    VRBO

    Precise Realty presents The Canal Breeze Retreat

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    St. Armand's Canal-Front Pool Home steps to the beach! This gem, ranch style home estate has been completely rebuilt ...

    From $1404 per night (USD)

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  • Crystal Sands Unit 806 - Beachfront
    From $645 per night (USD)

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    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 $645 per night (USD)

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  • Crystal Sands Villa 13 - Private Beach
    From $401 per night (USD)

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    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 $401 per night (USD)

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    Details
  • Crystal Sands Tower Unit 203 - Beachfront
    From $616 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 $616 per night (USD)

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    Details
  • Crystal Sands Tower Unit 805 - Beachfront
    From $611 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 $611 per night (USD)

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    Details
  • Crystal Sands Villa 17 - Private Beach
    From $436 per night (USD)

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    Crystal Sands Villa 17 - Private Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $436 per night (USD)

    VRBO

    Details
  • Crystal Sands Tower Unit 307 - Beachfront
    From $497 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 $497 per night (USD)

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    Details
  • Condo# 204 2 Bedroom 1 Bath condo is steps to the white powdered  sand of Siesta Key
    From $279 per night (USD)

    VRBO

    Condo# 204 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 $279 per night (USD)

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  • Crystal Sands Tower Unit 1204 - Beachfront
    From $627 per night (USD)

    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 ...

    From $627 per night (USD)

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    Details
  • Crystal Sands Tower Unit 1004 - Beachfront
    From $573 per night (USD)

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    Crystal Sands Tower Unit 1004 - Beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Affectionately called "The Perch", unit #1004 has been in our family since the building was nothing more than a blueprin ...

    From $573 per night (USD)

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    Details
  • Crystal Sands Tower Unit 404 - Beachfront
    From $671 per night (USD)

    Expedia

    Crystal Sands Tower Unit 404 - Beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Breathtaking Views - Beachfront Condo - Completely Renovated Enjoy breathtaking views of the Gulf of Mexico and world-f ...

    From $671 per night (USD)

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  • Crystal Sands Tower Unit 305 - Beachfront
    From $563 per night (USD)

    VRBO

    Crystal Sands Tower Unit 305 - Beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Treat yourself to a completely remodeled and updated 3rd floor 2 bedroom 2 bath ocean front condo. Enjoy the beautiful ...

    From $563 per night (USD)

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    Details
  • Crystal Sands Tower Unit 502 - Beachfront
    From $567 per night (USD)

    Expedia

    Crystal Sands Tower Unit 502 - Beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    SONG OF SIESTA KEY!! Located on Beautiful #1 Award Winning White Sands of Siesta Key Beach with panoramic views from 30 ...

    From $567 per night (USD)

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    Details
  • Crystal Sands Tower Unit 506 - Beachfront
    From $520 per night (USD)

    VRBO

    Crystal Sands Tower Unit 506 - Beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Treat yourself to a completely remodeled and updated 5th floor 2 bedroom 2 bath ocean front condo. Enjoy the beautiful ...

    From $520 per night (USD)

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    Details
  • Crystal Sands Tower Unit 704 - Beachfront
    From $567 per night (USD)

    Expedia

    Crystal Sands Tower Unit 704 - Beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy the best of Crystal Sands in this beachy, contemporary 2-bedroom, 2 bath condo overlooking the 2011 and 2017 Best ...

    From $567 per night (USD)

    Expedia

    Details
  • Crystal Sands Tower Unit 710 - Beachfront
    From $567 per night (USD)

    VRBO

    Crystal Sands Tower Unit 710 - 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 $567 per night (USD)

    VRBO

    Details
  • Crystal Sands Villa 20 - Private Beach
    From $417 per night (USD)

    Expedia

    Crystal Sands Villa 20 - Private Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $417 per night (USD)

    Expedia

    Details
  • Crystal Sands Tower Unit 104 - Beachfront
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    Crystal Sands Tower Unit 104 - 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 ...

    Click For Pricing

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  • Crystal Sands Tower Unit 205 - Beachfront
    From $611 per night (USD)

    Expedia

    Crystal Sands Tower Unit 205 - 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 $611 per night (USD)

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    Details
  • Condo # 111 Luxurious Living by Siesta Beach in this renovated 2b/1b ground floor unit
    From $270 per night (USD)

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    Condo # 111 Luxurious Living by Siesta Beach in this renovated 2b/1b ground floor unit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    NOW WITH PRIVATE WiFi. Our condo is beautifully decorated with elegant touch & taste. It was recently renovated with st ...

    From $270 per night (USD)

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  • Direct Gulf View from 3rd Floor - B307, Free Boat Docks & WiFi
    From $378 per night (USD)

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    Direct Gulf View from 3rd Floor - B307, Free Boat Docks & WiFi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy our third floor upgraded apartment with new wood plank flooring, including on the lanai, new leather couches,upgra ...

    From $378 per night (USD)

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    Details
  • Coastal Getaway minutes from Siesta Key, America’s #1 Beach
    From $320 per night (USD)

    VRBO

    Coastal Getaway minutes from Siesta Key, America’s #1 Beach

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Set back off the road on a quiet lane, enjoy this newly furnished, cozy modern coastal home. With this 3 bedroom, 2 bat ...

    From $320 per night (USD)

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    Details
  • Condo# 319 Located across the street from Siesta Key Beach, Gulf and Pool View Condo!!
    From $254 per night (USD)

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    Condo# 319 Located across the street from Siesta Key Beach, Gulf and Pool View Condo!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Updated 2BR Condo | Pool & Ocean Views | Steps to Beach & Village | Sleeps 6 Escape to paradise at La Siesta 319, a beau ...

    From $254 per night (USD)

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  • Condo# 308 Modern Siesta Key 2BR Condo – Steps from the Beach
    From $271 per night (USD)

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    Condo# 308 Modern Siesta Key 2BR Condo – Steps from the Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Your perfect vacation awaits in this Two Bedroom / One Bath Condo steps from the famous Siesta Key Beach, always named o ...

    From $271 per night (USD)

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  • Condo# 208 Charming Condo at La Siesta with Partial Beach Views \Your home away from home\
    From $260 per night (USD)

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    Condo# 208 Charming Condo at La Siesta with Partial Beach Views \"Your home away from home\"

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Now with private Wifi. This Two Bedroom, One Bath condo is just steps to the white, powdered sugar sand of Siesta Key. ...

    From $260 per night (USD)

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    Details
  • Chic Sarasota Cottage: Near Beaches & Downtown!
    From $221 per night (USD)

    VRBO

    Chic Sarasota Cottage: Near Beaches & Downtown!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Plan your next beach escape at this gorgeous 1-bedroom, 1-bath Sarasota vacation rental! Perfect for couples or small gr ...

    From $221 per night (USD)

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  • Siesta Keys Home w/ Deck Half Mile to Turtle Beach
    From $350 per night (USD)

    VRBO

    Siesta Keys Home w/ Deck Half Mile to Turtle Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Begin your sunkissed adventures at this 2-bedroom, 1-bathroom vacation rental condo in Siesta Key. This coastal condo bo ...

    From $350 per night (USD)

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  • Gulf View from Lanai or Master - B308 with Boat Dock & Free WiFi
    From $302 per night (USD)

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    Gulf View from Lanai or Master - B308 with Boat Dock & Free WiFi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This lovely and colorful 3rd floor unit has an incredible view of the Gulf of Mexico to enjoy with your family members f ...

    From $302 per night (USD)

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  • Condo# 311 Extraordinary Beach view! 2b/1b Fully Renovated, Walk in shower, Custom Kitchen
    From $316 per night (USD)

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    Condo# 311 Extraordinary Beach view! 2b/1b Fully Renovated, Walk in shower, Custom Kitchen

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Now with private WiFi. Your perfect vacation awaits in this Two Bedroom/One Bath condo right next to the famous Siesta K ...

    From $316 per night (USD)

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    Details