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  • Anchorage 504
    From $382 per night (USD)

    VRBO

    Anchorage 504

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tenn ...

    From $382 per night (USD)

    VRBO

    Details
  • Anchorage 204
    From $353 per night (USD)

    Expedia

    Anchorage 204

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tenn ...

    From $353 per night (USD)

    Expedia

    Details
  • Anchorage 905
    From $382 per night (USD)

    VRBO

    Anchorage 905

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tenn ...

    From $382 per night (USD)

    VRBO

    Details
  • Anchorage 406
    From $289 per night (USD)

    Expedia

    Anchorage 406

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tenn ...

    From $289 per night (USD)

    Expedia

    Details
  • Anchorage 507
    From $363 per night (USD)

    VRBO

    Anchorage 507

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tenn ...

    From $363 per night (USD)

    VRBO

    Details
  • Anchorage 405
    From $316 per night (USD)

    Expedia

    Anchorage 405

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Your tropical paradise awaits you in this beautiful 2-bedroom 2-bathroom home located in beautiful Siesta Key. Just a sh ...

    From $316 per night (USD)

    Expedia

    Details
  • Anchorage 704
    From $355 per night (USD)

    VRBO

    Anchorage 704

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tenn ...

    From $355 per night (USD)

    VRBO

    Details
  • Anchorage 403
    From $367 per night (USD)

    Expedia

    Anchorage 403

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium facing the Gulf of Mexico in be ...

    From $367 per night (USD)

    Expedia

    Details
  • Anchorage 807
    From $378 per night (USD)

    VRBO

    Anchorage 807

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to The Anchorage unit 807 on beautiful Siesta Key. We invite you to stay in our spacious 1,250 square foot 2 b ...

    From $378 per night (USD)

    VRBO

    Details
  • Anchorage 711
    From $550 per night (USD)

    Expedia

    Anchorage 711

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    We invite you to stay in our spacious 2,400 square foot 3 bedroom 2.5 bathroom condominium at The Anchorage Yacht and Te ...

    From $550 per night (USD)

    Expedia

    Details
  • Anchorage PH-6
    From $391 per night (USD)

    VRBO

    Anchorage PH-6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Penthouse Unit with Sweeping Views of the Gulf of Mexico and the Inter-Coastal Waterway We invite you to stay in our sp ...

    From $391 per night (USD)

    VRBO

    Details
  • Crystal Sands Tower Unit 706 - Beachfront
    From $535 per night (USD)

    Expedia

    Crystal Sands Tower Unit 706 - 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 $535 per night (USD)

    Expedia

    Details
  • Modern & Cozy Home, close to beach & Dearborn St!
    From $185 per night (USD)

    VRBO

    Modern & Cozy Home, close to beach & Dearborn St!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Beautiful, cozy, modern and recently renovated home!! Only 7 min drive to Manasota Key beach, 1 mile from Dearborn Stre ...

    From $185 per night (USD)

    VRBO

    Details
  • Steps to Gulf of Mexico
    Click For Pricing

    Expedia

    Steps to Gulf of Mexico

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Walk to the Gulf of Mexico which is just a half block away. Three blocks to downtown Venice where you will find shopping ...

    Click For Pricing

    Expedia

    Details
  • Perfect location!<br>Beautiful!<br>Clean!<br>Heated swimming pool!<br>
    From $209 per night (USD)

    VRBO

    Perfect location!<br>Beautiful!<br>Clean!<br>Heated swimming pool!<br>

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Come stay in this 768 sq. ft, 1 bedroom, 1 bathroom condominium with a quiet,private,fenced in backyard. Beautiful new t ...

    From $209 per night (USD)

    VRBO

    Details
  • Tastefully remodeled pool  home 7 minutes from the Siesta Key Beach
    From $475 per night (USD)

    Expedia

    Tastefully remodeled pool home 7 minutes from the Siesta Key Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Tastefully remodeled home only 7 minutes from stunning Siesta Key Beach! As you walk in, you are greeted with all styli ...

    From $475 per night (USD)

    Expedia

    Details
  • Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
    From $625 per night (USD)

    VRBO

    Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    One level FL Beach Cottage, 3rd house from Beach Path on N end of Lido Beach. This is a rare find in a nice quiet neighb ...

    From $625 per night (USD)

    VRBO

    Details
  • Lido Key Villa! Walk to Beach, St. Armand's Circle, Heated Pool, & Perfect Location!
    From $282 per night (USD)

    Expedia

    Lido Key Villa! Walk to Beach, St. Armand's Circle, Heated Pool, & Perfect Location!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

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

    From $282 per night (USD)

    Expedia

    Details
  • Beach front paradise located in a Condo Building Beach front Penthouse!
    From $629 per night (USD)

    VRBO

    Beach front paradise located in a Condo Building Beach front Penthouse!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Beautiful brand new three bedroom which has three king-size beds three full bathroom penthouse condo At the #1 beach. ...

    From $629 per night (USD)

    VRBO

    Details
  • Pool Home, Steps to Secluded Beach Access
    From $480 per night (USD)

    Expedia

    Pool Home, Steps to Secluded Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Take a deep breath and get ready to relax! This 3 bedroom, 2 bathroom pool home is the perfect place for your next vaca ...

    From $480 per night (USD)

    Expedia

    Details
  • A Bayside Treasure - Outstanding Waterfront Views!!
    From $241 per night (USD)

    VRBO

    A Bayside Treasure - Outstanding Waterfront Views!!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Our spacious (1400 sq. ft.) luxurious third floor condominium has been completely remodeled and professionally decorated ...

    From $241 per night (USD)

    VRBO

    Details
  • Charming Private Garden Cottage hide away in the heart of Sarasota
    From $121 per night (USD)

    Expedia

    Charming Private Garden Cottage hide away in the heart of Sarasota

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $121 per night (USD)

    Expedia

    Details
  • Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook
    From $1895 per night (USD)

    VRBO

    Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook

    Bedrooms:
    9
    Bathrooms:
    8
    Sleeps:
    18

    Ocean Overlook by Siesta Key Luxury Rental Properties Home in Sarasota, Florida Your dream vacation awaits at Ocean O ...

    From $1895 per night (USD)

    VRBO

    Details
  • Spacious & Quiet at Fishermans Haven on Siesta Key. Private Beach, Heated Pool, Fish on the Bay. FH6
    From $204 per night (USD)

    Expedia

    Spacious & Quiet at Fishermans Haven on Siesta Key. Private Beach, Heated Pool, Fish on the Bay. FH6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautiful, Spacious & Quiet at Fisherman's Haven on Siesta Key. Private Beach, Fish on the Bay, Gated. Beautifully appo ...

    From $204 per night (USD)

    Expedia

    Details
  • Beautiful one bedroom condo on Siesta Key.  minutes from Siesta key Beach!
    From $149 per night (USD)

    VRBO

    Beautiful one bedroom condo on Siesta Key. minutes from Siesta key Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Beautiful 4'th floor condo with elevator access. screened in lanai, all the essentials, and beach chairs, umbrellas, coo ...

    From $149 per night (USD)

    VRBO

    Details
  • Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
    From $397 per night (USD)

    Expedia

    Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Turtles and Toes is a peaceful and relaxing refuge that will refresh your mind and soul. The 600 square foot updated and ...

    From $397 per night (USD)

    Expedia

    Details
  • WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US
    From $371 per night (USD)

    VRBO

    WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Siesta Key is situated on what is known as a barrier island. It measures 7 miles long, lies just offshore from Sarasota, ...

    From $371 per night (USD)

    VRBO

    Details
  • Upscale Hidden Jewel 2 miles to Nokomis Beach!
    From $321 per night (USD)

    Expedia

    Upscale Hidden Jewel 2 miles to Nokomis Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This is the place for you if you like tranquility, but close to the beach and walking distance to restaurants. Our place ...

    From $321 per night (USD)

    Expedia

    Details
  • Condo Close To The Beach
    From $95 per night (USD)

    VRBO

    Condo Close To The Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Wow! Come check out this beautifully remodeled condo in the heart of Venice. This luxury condo boasts 2 bedrooms and 2 b ...

    From $95 per night (USD)

    VRBO

    Details
  • Anchorage 208
    From $316 per night (USD)

    Expedia

    Anchorage 208

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tenn ...

    From $316 per night (USD)

    Expedia

    Details
  • Anchorage 207
    From $362 per night (USD)

    VRBO

    Anchorage 207

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tenn ...

    From $362 per night (USD)

    VRBO

    Details
  • Cozy South Venice Coastal Getaway – 10 Minutes from sandy beaches
    From $193 per night (USD)

    Expedia

    Cozy South Venice Coastal Getaway – 10 Minutes from sandy beaches

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your coastal escape in South Venice, Florida! This charming beach house offers the perfect blend of relaxatio ...

    From $193 per night (USD)

    Expedia

    Details
  • Very clean 3 bedroom, 2 bath. Easy walk to Siesta Key Beach & Restaurants.
    From $232 per night (USD)

    VRBO

    Very clean 3 bedroom, 2 bath. Easy walk to Siesta Key Beach & Restaurants.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    This home is 1/2 mile from Siesta Key Beach. It is furnished with quality. Your stay includes super-fast WiFi, a washer/ ...

    From $232 per night (USD)

    VRBO

    Details
  • Ventana Rosa | Beautiful Sarasota Home Near Siesta Key w/ Private Pool & Large Outdoor Space
    From $430 per night (USD)

    Expedia

    Ventana Rosa | Beautiful Sarasota Home Near Siesta Key w/ Private Pool & Large Outdoor Space

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    🌴 Ventana Rosa | Heated Pool + Lush Tropical Outdoor Living 💖 Why You'll Love This Home Wrapped in tropical foliage a ...

    From $430 per night (USD)

    Expedia

    Details
  •  amazing apartment on the beach. With  warm pool .
    From $132 per night (USD)

    VRBO

    amazing apartment on the beach. With warm pool .

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    On the landscaped side of the complex, you will hear a calming waterfall right from your tropical patio! The apartment ...

    From $132 per night (USD)

    VRBO

    Details
  • “Casa Concord: 3BR-2BA Home with Private SaltH20 Pool, 2 Miles from Siesta Key”
    From $406 per night (USD)

    VRBO

    “Casa Concord: 3BR-2BA Home with Private SaltH20 Pool, 2 Miles from Siesta Key”

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Just 2 miles to Crescent Beach, Siesta Key, 3.9 miles to Siesta Key Beach! Ranked the #1 Beach in America and the World, ...

    From $406 per night (USD)

    VRBO

    Details
  • Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach
    From $305 per night (USD)

    VRBO

    Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent) Located ...

    From $305 per night (USD)

    VRBO

    Details
  • Relax`n - Beautiful newer South Venice home with pool and spa
    From $265 per night (USD)

    Expedia

    Relax`n - Beautiful newer South Venice home with pool and spa

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful newer South Venice pool home in immaculate condition. Open plan with gleaming tiled floors throughout, high ce ...

    From $265 per night (USD)

    Expedia

    Details
  • Beautiful 2025 renovated - 550 Sq Ft  Patio - across street from beach
    From $441 per night (USD)

    VRBO

    Beautiful 2025 renovated - 550 Sq Ft Patio - across street from beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Long term rental available from May 1 - Dec 15th - please contact for details UV OZONE Sanitized between each guest. ...

    From $441 per night (USD)

    VRBO

    Details
  • Longboat Key Escape–2BR Beachplace Condo Near the Ocean Unit 5-301 by RVA
    From $329 per night (USD)

    Expedia

    Longboat Key Escape–2BR Beachplace Condo Near the Ocean Unit 5-301 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    RVA proudly presents an exquisite two-bedroom, two-bathroom residence nestled in building 5, offering unparalleled Gulf ...

    From $329 per night (USD)

    Expedia

    Details
  • Venice Pool Home- Breezy Inn
    From $365 per night (USD)

    VRBO

    Venice Pool Home- Breezy Inn

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    3BR Heated Pool Home Minutes from the Gulf! Get ready to unwind in paradise! This newly remodeled 3-bedroom, 2-bath heat ...

    From $365 per night (USD)

    VRBO

    Details
  • BH · 2/2 Beach House Apt on Siesta Key
    From $727 per night (USD)

    Expedia

    BH · 2/2 Beach House Apt on Siesta Key

    Bedrooms:
    1
    Bathrooms:
    16
    Sleeps:
    6

    Summary: Siesta Key Waterfront Apartment. Sleeps 6. Split plan 2 bedroom, 2 full bathroom “Beach House” w/ a full kitch ...

    From $727 per night (USD)

    Expedia

    Details
  • Hotel Studio (Ground Level) - Unit C
    From $175 per night (USD)

    VRBO

    Hotel Studio (Ground Level) - Unit C

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $175 per night (USD)

    VRBO

    Details
  • Hotel Studio (Ground Level) - Unit B
    From $196 per night (USD)

    Expedia

    Hotel Studio (Ground Level) - Unit B

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $196 per night (USD)

    Expedia

    Details
  • Escape Casey Key Hotel & Marina - 1 Bed 1 Bath  K Bed Villa 4b
    From $215 per night (USD)

    VRBO

    Escape Casey Key Hotel & Marina - 1 Bed 1 Bath K Bed Villa 4b

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $215 per night (USD)

    VRBO

    Details
  • 2 Bedroom/1 Bath Villa (Ground Level) - Unit 5
    From $306 per night (USD)

    Expedia

    2 Bedroom/1 Bath Villa (Ground Level) - Unit 5

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $306 per night (USD)

    Expedia

    Details
  • 2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A
    From $400 per night (USD)

    VRBO

    2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $400 per night (USD)

    VRBO

    Details
  • 1 Bedroom/1 Bath Villa Ground Level - Unit 9
    From $242 per night (USD)

    Expedia

    1 Bedroom/1 Bath Villa Ground Level - Unit 9

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $242 per night (USD)

    Expedia

    Details
  • Emerald Palms Unit A
    From $121 per night (USD)

    VRBO

    Emerald Palms Unit A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This beautiful, updated 1 bedroom 1 bath cottage is located right in the heart of Englewood, Fl. on Lemon Bay. Fully equ ...

    From $121 per night (USD)

    VRBO

    Details
  • 3 Bedroom/3 Bath Townhouse - Unit 2
    From $392 per night (USD)

    Expedia

    3 Bedroom/3 Bath Townhouse - Unit 2

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $392 per night (USD)

    Expedia

    Details
  • Hotel Studio (Ground Level) - Unit A
    From $175 per night (USD)

    VRBO

    Hotel Studio (Ground Level) - Unit A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $175 per night (USD)

    VRBO

    Details
  • 3 Bedroom/3 Bath Townhouse - Unit 3
    From $487 per night (USD)

    Expedia

    3 Bedroom/3 Bath Townhouse - Unit 3

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $487 per night (USD)

    Expedia

    Details
  • 2 Bedroom/2 Bath Villa (Ground Level) - Unit 7
    From $400 per night (USD)

    VRBO

    2 Bedroom/2 Bath Villa (Ground Level) - Unit 7

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $400 per night (USD)

    VRBO

    Details
  • 2 Bedroom/1 Bath Villa (Ground Level) - Unit 13
    From $381 per night (USD)

    Expedia

    2 Bedroom/1 Bath Villa (Ground Level) - Unit 13

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $381 per night (USD)

    Expedia

    Details
  • 2 Bedroom/2 Bath Villa (Second Level) - Unit 6
    From $380 per night (USD)

    VRBO

    2 Bedroom/2 Bath Villa (Second Level) - Unit 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $380 per night (USD)

    VRBO

    Details
  • ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8
    From $330 per night (USD)

    Expedia

    ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $330 per night (USD)

    Expedia

    Details
  • 2 Bedroom/2 Bath Villa (Second Level) - Unit 10
    From $477 per night (USD)

    VRBO

    2 Bedroom/2 Bath Villa (Second Level) - Unit 10

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $477 per night (USD)

    VRBO

    Details
  • 2 Bedroom/1 Bath Villa (Ground Level) - Unit 12
    From $380 per night (USD)

    Expedia

    2 Bedroom/1 Bath Villa (Ground Level) - Unit 12

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $380 per night (USD)

    Expedia

    Details
  • 2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C
    From $428 per night (USD)

    VRBO

    2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $428 per night (USD)

    VRBO

    Details
  • 3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B
    From $610 per night (USD)

    Expedia

    3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $610 per night (USD)

    Expedia

    Details
  • Casa Bella Vita | Luxury Home w/ Heated Pool, Ping Pong Table, & Walking Distance to Crescent Beach!
    Click For Pricing

    VRBO

    Casa Bella Vita | Luxury Home w/ Heated Pool, Ping Pong Table, & Walking Distance to Crescent Beach!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to Casa Bella Vita – Your Ultimate Siesta Key Escape! Discover the charm and elegance of Casa Bella Vita, a stu ...

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  • Escape Casey Key Hotel & Marina - Deluxe 3 Bedroom 3 Bath Villa 2 K 1 Q  1
    From $392 per night (USD)

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    Escape Casey Key Hotel & Marina - Deluxe 3 Bedroom 3 Bath Villa 2 K 1 Q 1

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Experience Escape’s brand new luxury villas including one bedroom hotel units, two bed two bath and three bed three bath ...

    From $392 per night (USD)

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  • Bird Bay Villa
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    Bird Bay Villa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Fully furnished Bird Bay Villa that is bright & airy with off-street private driveway parking. It features 2 bedrooms wi ...

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  • Coastal 3BR Villa – Lil’ Nauti with Pool & Waterfront Access
    From $474 per night (USD)

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    Coastal 3BR Villa – Lil’ Nauti with Pool & Waterfront Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    *Fully Renovated as of February 2025* Your own private Siesta Key villa that's a little bit tropical, a little bit salt ...

    From $474 per night (USD)

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  • Siesta Key Beach Condo #1 Beach
    From $302 per night (USD)

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    Siesta Key Beach Condo #1 Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This super cute 1 bed, 1 bath condo directly opposite one of the most beautiful beaches in the world is available and re ...

    From $302 per night (USD)

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  • Beautiful Venice Beach Condo
    From $193 per night (USD)

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    Beautiful Venice Beach Condo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Prime location one block from the beach with a marina, dining, and lounge nearby. Two minute walk to three different bea ...

    From $193 per night (USD)

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    Details
  • Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
    From $301 per night (USD)

    VRBO

    Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cottage style 2 bedroom 1 bath condo in Siesta Key is just a 2-3 min walk to the Pool, Beach, Restaurants and shops. ((A ...

    From $301 per night (USD)

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  • Condo# 314 Siesta Key 3rd Flr 2b/2b unit; Open kitchen; newly renovated master shower
    From $307 per night (USD)

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    Condo# 314 Siesta Key 3rd Flr 2b/2b unit; Open kitchen; newly renovated master shower

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

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

    From $307 per night (USD)

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  • Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
    From $311 per night (USD)

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    Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cottage style 2 bedroom 1 bath condo in Siesta Key is just a 2-3 min walk to the Pool, Beach, Restaurants and shops. (Al ...

    From $311 per night (USD)

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  • Paradise!  Gulf beach, On bay, bike, fish, kayak, relax, shop, swim, tennis.....
    From $143 per night (USD)

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    Paradise! Gulf beach, On bay, bike, fish, kayak, relax, shop, swim, tennis.....

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful condo located on 2nd floor. End unit overlooking beautiful tropical plants and offering natural light ! Turn ...

    From $143 per night (USD)

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  • Contemporary, Downtown location, Pool, Spa & Sauna, very close to Beaches
    From $482 per night (USD)

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    Contemporary, Downtown location, Pool, Spa & Sauna, very close to Beaches

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Gorgeous courtyard pool home features high end quality construction throughout with high end upgrades, open split floor ...

    From $482 per night (USD)

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  • Beachplace Living – Walk to Beach, Swim, Play & Unwind #11-303 Condo by RVA
    From $291 per night (USD)

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    Beachplace Living – Walk to Beach, Swim, Play & Unwind #11-303 Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    RVA offers this comfortably appointed two-bedroom, two-bathroom condominium in the desirable gated community of Beachpla ...

    From $291 per night (USD)

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  • Paradise Found-heated pool & spa-bikes, game room-close to beach & Legacy Trail
    From $312 per night (USD)

    VRBO

    Paradise Found-heated pool & spa-bikes, game room-close to beach & Legacy Trail

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Paradise awaits at this charming 3-bedroom vacation home in the heart of South Venice. Nestled just minutes from the bea ...

    From $312 per night (USD)

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  • Large Siesta Key Home On Water With Pool/Spa
    From $678 per night (USD)

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    Large Siesta Key Home On Water With Pool/Spa

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Welcome to “Siesta Retreat”… a grand 5 bedroom 4 bath vacation home right on the canal with an awesome pool and hot tub ...

    From $678 per night (USD)

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  • Palm Bay Club!!! RESORT STYLE LIVING ON SIESTA KEY!!!  Beach to Bay!!!
    From $428 per night (USD)

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    Palm Bay Club!!! RESORT STYLE LIVING ON SIESTA KEY!!! Beach to Bay!!!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Walk onto the Famous Siesta Key beach, voted #1 beach in the US, with the worlds whitest and softest sand. This complex ...

    From $428 per night (USD)

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  • Wonderful Home with Heated Pool near Beaches and Shamrock Park free wifi
    From $202 per night (USD)

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    Wonderful Home with Heated Pool near Beaches and Shamrock Park free wifi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Located a block from Shamrock Park and close to 4 different beaches, you'll enjoy this completely updated 2/2/1 heated p ...

    From $202 per night (USD)

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  • Private 2 Bedroom 1 bathroom house.  private pool and SPA. Close to beaches
    From $197 per night (USD)

    VRBO

    Private 2 Bedroom 1 bathroom house. private pool and SPA. Close to beaches

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Located just 10 minutes away from Nokomis beach at Casey Key, and 5 minutes to the Oscar Scherer State Park. You have e ...

    From $197 per night (USD)

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  • Lovely Condo with View of Lido beach and walking distance to St Armand's Circle
    From $235 per night (USD)

    VRBO

    Lovely Condo with View of Lido beach and walking distance to St Armand's Circle

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautifully renovated 2 bedroom, 2 bath, End unit in the highly sought after Lido Shores Condominium. The spacious and ...

    From $235 per night (USD)

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  • Spacious 2BR Sarasota Executive Suite – Suited for Business, Medical Stay, Beach
    From $378 per night (USD)

    VRBO

    Spacious 2BR Sarasota Executive Suite – Suited for Business, Medical Stay, Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The Property Welcome to one of the most exciting vacation rental properties in Sarasota. The Southside Village Executive ...

    From $378 per night (USD)

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  • Condo# 206 View Siesta Key Beach from balcony! LOCATION!
    From $299 per night (USD)

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    Condo# 206 View Siesta Key Beach from balcony! LOCATION!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy the beach for the 4th!...Week ending July 6th 20% off rental rate. LOCATION, LOCATION, LOCATION! Spacious, updat ...

    From $299 per night (USD)

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  • Kingston Arms Paradise!\n Saint  Armands Circle & Lido Beach!  Fully Equipped!
    From $182 per night (USD)

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    Kingston Arms Paradise!\n Saint Armands Circle & Lido Beach! Fully Equipped!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Kingston Arms Condominium, an exquisite retreat located on vibrant Saint Armands Circle in Sarasota, Florida. ...

    From $182 per night (USD)

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  • 3 Palms Inn- 2/3 bedroom heated pool house!
    From $333 per night (USD)

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    3 Palms Inn- 2/3 bedroom heated pool house!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    We are also the hosts for VRBO listing #1718910. We are experience host with great reviews. We have decided to add anoth ...

    From $333 per night (USD)

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    Details
  • Luxury and elegance in Venice
    From $449 per night (USD)

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    Luxury and elegance in Venice

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your luxurious, cozy, and relaxing, three bedroom, two bathroom, fully heated pool home in beautiful Venice, ...

    From $449 per night (USD)

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  • Gertrude's Siesta | 4-min Walk to Beach & Village with Tiki-Bar, Balcony, Tropical Patio!
    From $749 per night (USD)

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    Gertrude's Siesta | 4-min Walk to Beach & Village with Tiki-Bar, Balcony, Tropical Patio!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Casa Van Lopik Large 3BR home in the Siesta Key Village, 4-min walk to best beaches shopping dining and entertainment on ...

    From $749 per night (USD)

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  • Anchorage 310
    From $329 per night (USD)

    VRBO

    Anchorage 310

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tenn ...

    From $329 per night (USD)

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    Details
  • Walk to Siesta Key Beach & Village | Private Patio | Prime Location!
    From $385 per night (USD)

    Expedia

    Walk to Siesta Key Beach & Village | Private Patio | Prime Location!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Village Studio Top location on the island! Apartment with full kitchen, private patio, quiet gated courtyard, in wo ...

    From $385 per night (USD)

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    Details
  • ☆ KING Bed in Master • 1st Floor • Heated Pool • ¼ mile walk to Siesta Key ☆
    From $282 per night (USD)

    VRBO

    ☆ KING Bed in Master • 1st Floor • Heated Pool • ¼ mile walk to Siesta Key ☆

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to the sugary sands of Siesta Key, just one-quarter mile from this well-appointed and stylish vacation condo! It ...

    From $282 per night (USD)

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  • Sunsets at Gulf of Mexico
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    Sunsets at Gulf of Mexico

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Location, location, location 1 block to the beach, 3 blocks to restaurants and shopping Venice inlet, Sharkey's at the p ...

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  • Gertrude's Siesta | 4-min Walk to Beach & Village with Tiki-Bar, Balcony, Tropical Patio!
    From $613 per night (USD)

    VRBO

    Gertrude's Siesta | 4-min Walk to Beach & Village with Tiki-Bar, Balcony, Tropical Patio!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Casa Van Lopik Large 3BR home in the Siesta Key Village, 4-min walk to best beaches shopping dining and entertainment on ...

    From $613 per night (USD)

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    Details
  • 2-3 bedroom pool home just 5 minutes to Beach. Bicycles & beach gear included!
    From $229 per night (USD)

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    2-3 bedroom pool home just 5 minutes to Beach. Bicycles & beach gear included!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    “Pool Villa by the Beach” located in South Venice - a recently remodeled home that's less than 2 miles to the famous Ma ...

    From $229 per night (USD)

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  • Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
    From $270 per night (USD)

    VRBO

    Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    “GEM” at Barefoot Bungalows is a 2 bedroom, 1 bath, fully furnished villa just minute walk to the beach! This 1945 Tripl ...

    From $270 per night (USD)

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  • Beautiful Villa in Private Resort-Style Community
    From $276 per night (USD)

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    Beautiful Villa in Private Resort-Style Community

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This spacious 2-bed/2-bath corner villa has 1,350 sq. ft. of fully tiled living space, attached garage and screened-in l ...

    From $276 per night (USD)

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  • Ground-Level Condo | Beach Access, Pool & Canal Views | Walk to Everything
    From $292 per night (USD)

    VRBO

    Ground-Level Condo | Beach Access, Pool & Canal Views | Walk to Everything

    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 $292 per night (USD)

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  • Tiny House Margarita - Sleeps 6
    From $180 per night (USD)

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    Tiny House Margarita - Sleeps 6

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Summary: This Tiny House began its life in our home state of Pennsylvania. Originally, it was meant to be a vacation hom ...

    From $180 per night (USD)

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  • Castel Del Mare Condo for rent
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    Castel Del Mare Condo for rent

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Sarasota vacation condo is located in Castel Del Mare Condominum Complex, on the intercoastal waterway between Sarasota ...

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  • Cozy Home away from Home - Central to Warm Mineral Springs and Englewood Beach
    From $175 per night (USD)

    VRBO

    Cozy Home away from Home - Central to Warm Mineral Springs and Englewood Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Private house, with Florida charm. Less than 15 min to Warm Mineral Springs 5 miles to Englewood Beach. Private back ya ...

    From $175 per night (USD)

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    Details
  • Just remodeled, professionally decorated bright and airy!
    From $2187 per night (USD)

    VRBO

    Just remodeled, professionally decorated bright and airy!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Oceanfront CLEAN condo on BEACH! Total remodel and professionally Decorated with a coastal vibe. New shiplap, new mirro ...

    From $2187 per night (USD)

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    Details
  • Pre furnished 3 bed 2 bath house nearby the beach
    From $233 per night (USD)

    VRBO

    Pre furnished 3 bed 2 bath house nearby the beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The recently remodeled house comes pre furnished with kitchen appliances including a washer and dryer, wireless internet ...

    From $233 per night (USD)

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  • Newly Renovated - 2BR Beachfront Condo by FVC
    From $379 per night (USD)

    VRBO

    Newly Renovated - 2BR Beachfront Condo by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    NEWLY RENOVATED!! A beachfront condominium managed by Florida Vacation Connection is located on the world-renowned Long ...

    From $379 per night (USD)

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  • Beachview 2 BR / 2 BA Beachplace condo by FVC
    From $294 per night (USD)

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    Beachview 2 BR / 2 BA Beachplace condo by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beachplace 5-402 | Pond & Beach Views | Florida Vacation Connection Welcome to Beachplace 5-402, your serene getaway on ...

    From $294 per night (USD)

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    Details