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  • Ultimate Family Reunion: Pool, Game Room, 3 mins to Beach - Surf View
    From $1584 per night (USD)

    VRBO

    Ultimate Family Reunion: Pool, Game Room, 3 mins to Beach - Surf View

    Bedrooms:
    8
    Bathrooms:
    8
    Sleeps:
    22

    Surf View by Siesta Key Luxury Rental Properties Home in Siesta Key, FL Gather your family for an unforgettable reunion ...

    From $1584 per night (USD)

    VRBO

    Details
  • Huge Yard with Heated Pool, Steps to Beach - The Pool House
    From $1238 per night (USD)

    Expedia

    Huge Yard with Heated Pool, Steps to Beach - The Pool House

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    16

    The Pool House by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Welcome to The Pool House, a gorgeou ...

    From $1238 per night (USD)

    Expedia

    Details
  • Perfect for Families, Steps to Siesta Key Beach and Village!
    From $528 per night (USD)

    VRBO

    Perfect for Families, Steps to Siesta Key Beach and Village!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Fins Up by Siesta Key Luxury Rental Properties Duplex in Siesta Key, FL Perfect for Families! Amazing 3 bedroom, 2 bat ...

    From $528 per night (USD)

    VRBO

    Details
  • 3 houses from the Beach! Private Pool, Spa, and Ping Pong Table - Sunset Gulf
    From $1632 per night (USD)

    Expedia

    3 houses from the Beach! Private Pool, Spa, and Ping Pong Table - Sunset Gulf

    Bedrooms:
    5
    Bathrooms:
    8
    Sleeps:
    25

    Sunset Gulf by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Discover your dream beach retreat at S ...

    From $1632 per night (USD)

    Expedia

    Details
  • Siesta Home with Pool & Waterslide - Sunset Splash
    From $1867 per night (USD)

    VRBO

    Siesta Home with Pool & Waterslide - Sunset Splash

    Bedrooms:
    7
    Bathrooms:
    8
    Sleeps:
    23

    Sunset Splash by Siesta Key Luxury Rental Properties Home in Siesta Key, FL Welcome to Sunset Splash! This legendary gr ...

    From $1867 per night (USD)

    VRBO

    Details
  • Tiny House Flamingo - free WiFi
    From $183 per night (USD)

    Expedia

    Tiny House Flamingo - free WiFi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Flamingo once was occupied as a permanent residence and now resides with us at Tiny House Siesta. Master bedroo ...

    From $183 per night (USD)

    Expedia

    Details
  • Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly
    From $698 per night (USD)

    VRBO

    Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Bimini Breeze by Siesta Key Luxury Rental Properties Home in Siesta Key, FL Less than a block away from Siesta Key Vill ...

    From $698 per night (USD)

    VRBO

    Details
  • Steps to Beach. Shared Pool Pet/Family Friendly. Parking Incl.
    From $553 per night (USD)

    Expedia

    Steps to Beach. Shared Pool Pet/Family Friendly. Parking Incl.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    11

    Island Sun by Siesta Key Luxury Rental Properties 559 Beach Rd B Siesta Key, Florida Welcome to Island Sun, a gorgeous ...

    From $553 per night (USD)

    Expedia

    Details
  • Dog Friendly, Private Heated Pool, Steps to the Beach and Shops! -Aruba
    From $825 per night (USD)

    VRBO

    Dog Friendly, Private Heated Pool, Steps to the Beach and Shops! -Aruba

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Aruba by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Welcome to Aruba! This fantastic vacation ho ...

    From $825 per night (USD)

    VRBO

    Details
  • Home with Gulf Views, Private Heated Pool, Spa, Game Room - Sunset View
    From $1685 per night (USD)

    Expedia

    Home with Gulf Views, Private Heated Pool, Spa, Game Room - Sunset View

    Bedrooms:
    5
    Bathrooms:
    8
    Sleeps:
    25

    Sunset View by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Welcome to Sunset View, a spectacular ...

    From $1685 per night (USD)

    Expedia

    Details
  • Altez Vacations Villa Steps from Beach and Pool.
    From $253 per night (USD)

    VRBO

    Altez Vacations Villa Steps from Beach and Pool.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    The Property Find yourself in the relaxing comforts of Siesta Villa Laughing Gull. A single-story stand-alone villa, loc ...

    From $253 per night (USD)

    VRBO

    Details
  • Perfect Location. Private Heated Pool/Spa w/ Waterslide
    From $1472 per night (USD)

    Expedia

    Perfect Location. Private Heated Pool/Spa w/ Waterslide

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    19

    At A Glance • 6-minute walk from the beach • Private pool, hot tub, and waterslide • Dog-friendly with host approval p ...

    From $1472 per night (USD)

    Expedia

    Details
  • Heated Pool/Spa w/ Waterslide. Rooftop Deck w/ Gulf Views. Water/Dock Access
    From $1458 per night (USD)

    VRBO

    Heated Pool/Spa w/ Waterslide. Rooftop Deck w/ Gulf Views. Water/Dock Access

    Bedrooms:
    6
    Bathrooms:
    8
    Sleeps:
    22

    Aloft on Canal by Siesta Key Luxury Rental Properties Home in Siesta Key, FL Welcome to Aloft on Canal! This luxurious ...

    From $1458 per night (USD)

    VRBO

    Details
  • Cozy and stylish house with wooded view in North Port, Fl
    From $205 per night (USD)

    Expedia

    Cozy and stylish house with wooded view in North Port, Fl

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Gorgeous fully furnished 3 bedroom 2 full bathroom house, highly desired North Port Area!Tropical and beach atmosphere a ...

    From $205 per night (USD)

    Expedia

    Details
  • Crystal Sands Tower Unit 901 - Beachfront
    Click For Pricing

    VRBO

    Crystal Sands Tower Unit 901 - 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

    VRBO

    Details
  • Tiny House Seashell - tiny living at the beach
    From $167 per night (USD)

    Expedia

    Tiny House Seashell - tiny living at the beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Our smallest Tiny House yet and on a private area of our property! It's tucked away in a fenced in area. Can yo ...

    From $167 per night (USD)

    Expedia

    Details
  • Tropical Oasis | Luxury Home on Siesta Key w/ Private Heated Pool/ Spa, Steps to Beach & Village!
    From $1898 per night (USD)

    VRBO

    Tropical Oasis | Luxury Home on Siesta Key w/ Private Heated Pool/ Spa, Steps to Beach & Village!

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    16

    Welcome to Tropical Oasis. This private family home is perfect for large families, with the ability to accommodate up to ...

    From $1898 per night (USD)

    VRBO

    Details
  • Casa Blanca Villa C16
    From $257 per night (USD)

    Expedia

    Casa Blanca Villa C16

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This newly renovated state of the art Villa boasts a newly remodeled and fully equipped gourmet kitchen with granite cou ...

    From $257 per night (USD)

    Expedia

    Details
  • Venice Vacation Rental with backyard lakefront
    From $181 per night (USD)

    VRBO

    Venice Vacation Rental with backyard lakefront

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Fully furnished Seasonal rental. The house is an updated 3 bath 2 bedroom with 1763 sq. ft. of living area. The home h ...

    From $181 per night (USD)

    VRBO

    Details
  • Venice Home w/ Fire Pit & Grill: 2 Mi to Beach!
    Click For Pricing

    Expedia

    Venice Home w/ Fire Pit & Grill: 2 Mi to Beach!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy all the coastal excitement surrounding Venice when you book this lovely 2-bedroom, 1-bath vacation rental! Boastin ...

    Click For Pricing

    Expedia

    Details
  • Paradise found in FLA
    Click For Pricing

    VRBO

    Paradise found in FLA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    This beautiful house offers three bedrooms and 2 bath. You’ll get a great night’s rest on the plush one king sized bed t ...

    Click For Pricing

    VRBO

    Details
  • 2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
    From $376 per night (USD)

    Expedia

    2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Perfect, private retreat! Time slips into Beach time, where nature guides your days and evenings. Fully renovated post 2 ...

    From $376 per night (USD)

    Expedia

    Details
  • Spectacular 8th FL panoramic views of the Gulf of Mexico and Downtown Sarasota
    Click For Pricing

    VRBO

    Spectacular 8th FL panoramic views of the Gulf of Mexico and Downtown Sarasota

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    2

    Gulf front panorama from this lovely 8th floor spacious condo available for $6,000/month starting January 1, 2021 (a 3-m ...

    Click For Pricing

    VRBO

    Details
  • Poolside Oasis with heated pool-7 min to beach-2 bikes-very private
    From $221 per night (USD)

    Expedia

    Poolside Oasis with heated pool-7 min to beach-2 bikes-very private

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to The Poolside! Our 2-bedroom 2 bathroom vacation home is located just 7 minutes away from the stunning Manasot ...

    From $221 per night (USD)

    Expedia

    Details
  • Unbeatable Ocean Views from Multiple Rooms and Balcony, Private Beach | Free Excursion
    From $647 per night (USD)

    VRBO

    Unbeatable Ocean Views from Multiple Rooms and Balcony, Private Beach | Free Excursion

    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 $647 per night (USD)

    VRBO

    Details
  • The Cozy Beach Suite of Sunny Sarasota!
    From $148 per night (USD)

    Expedia

    The Cozy Beach Suite of Sunny Sarasota!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Beautifully designed studio inspired guest suite in the heart of Sarasota ready for your next stay! We designed this sui ...

    From $148 per night (USD)

    Expedia

    Details
  • Sun, Sand and Savings Sarasota Deals
    From $396 per night (USD)

    VRBO

    Sun, Sand and Savings Sarasota Deals

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $396 per night (USD)

    VRBO

    Details
  • Resort Style Backyard! Private Dock and Beach Views! - Sea Spray
    From $1563 per night (USD)

    Expedia

    Resort Style Backyard! Private Dock and Beach Views! - Sea Spray

    Bedrooms:
    6
    Bathrooms:
    8
    Sleeps:
    22

    Sea Spray by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Welcome to Sea Spray! This eight-bedroom a ...

    From $1563 per night (USD)

    Expedia

    Details
  •  Located on Venice Island - Totally Remodeled Condo - 4 Blocks to the beach/town
    From $173 per night (USD)

    VRBO

    Located on Venice Island - Totally Remodeled Condo - 4 Blocks to the beach/town

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Totally remodeled 2BR/2BA condo on the second Floor of a 2 story complex. All brand new Furniture. Perfect location on t ...

    From $173 per night (USD)

    VRBO

    Details
  • 🌴💦 Fresh & updated 2/2 Siesta Key Condo~Fast WiFi, Pool, Private beach access!
    From $368 per night (USD)

    Expedia

    🌴💦 Fresh & updated 2/2 Siesta Key Condo~Fast WiFi, Pool, Private beach access!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to 𝗣𝗮𝗹𝗺 𝗩𝗶𝗲𝘄 at Siesta Dunes! Kick off your shoes, grab a drink and enjoy the palm view (our condo's nam ...

    From $368 per night (USD)

    Expedia

    Details
  • Fabulous Custom Home in Siesta Key!
    From $884 per night (USD)

    VRBO

    Fabulous Custom Home in Siesta Key!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Located just outside of vibrant Siesta Key Village, you find a 2600 square foot 4 bedroom, 3 Full, 1 .5 Bath Custom Home ...

    From $884 per night (USD)

    VRBO

    Details
  • 2 bedroom Condo, Bird Bay Village. REMODELED NEW NEW NEW
    Click For Pricing

    Expedia

    2 bedroom Condo, Bird Bay Village. REMODELED NEW NEW NEW

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    2 BR 2 BA, has a beautiful screened in lanai! NEW almost everything! New floors, paint, vanities, ALL new furniture, A ...

    Click For Pricing

    Expedia

    Details
  • Boaters Paradise Near Siesta Key Beach
    From $556 per night (USD)

    VRBO

    Boaters Paradise Near Siesta Key Beach

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    JAN 2024 DISCOUNT 2% rebate between Jan. 2-22. Exquisite new construction just over the 2 mile bridge from Siesta Key Be ...

    From $556 per night (USD)

    VRBO

    Details
  • Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct
    From $330 per night (USD)

    Expedia

    Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent) L ...

    From $330 per night (USD)

    Expedia

    Details
  • Florida's #1 Beach's Nearby!
    From $228 per night (USD)

    VRBO

    Florida's #1 Beach's Nearby!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to this newly 3/2 renovated home in sunny Sarasota Florida! This home features a modern style with a cozy feelin ...

    From $228 per night (USD)

    VRBO

    Details
  • Escape to Paradise: Updated Sarasota Retreat near Siesta Key Beach and Pool!
    From $191 per night (USD)

    Expedia

    Escape to Paradise: Updated Sarasota Retreat near Siesta Key Beach and Pool!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    3

    Unwind and reconnect at this beautifully updated vacation home in Sarasota! Perfect for families, this 2-bedroom, 2-bath ...

    From $191 per night (USD)

    Expedia

    Details
  • Find Your Happy Place on Siesta Key, Crescent Beach
    From $433 per night (USD)

    VRBO

    Find Your Happy Place on Siesta Key, Crescent Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    5 (five) day minimum stay. Immaculate Beach villa on beautiful Crescent Beach on #1 rated Siesta Key, Sarasota, Fl. Ful ...

    From $433 per night (USD)

    VRBO

    Details
  • Anchorage 305 - Siesta Chillin
    From $288 per night (USD)

    Expedia

    Anchorage 305 - Siesta Chillin

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We invite you to stay in our spacious condo managed by The Anchorage Community Rental Program. The Community Rental Prog ...

    From $288 per night (USD)

    Expedia

    Details
  • Anchorage 504 in Siesta Key
    From $327 per night (USD)

    VRBO

    Anchorage 504 in Siesta Key

    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 $327 per night (USD)

    VRBO

    Details
  • Anchorage 204 in Siesta Key
    From $307 per night (USD)

    Expedia

    Anchorage 204 in Siesta Key

    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 $307 per night (USD)

    Expedia

    Details
  • Anchorage 905 in Siesta Key
    From $327 per night (USD)

    VRBO

    Anchorage 905 in Siesta Key

    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 $327 per night (USD)

    VRBO

    Details
  • Anchorage 406 in Siesta Key
    From $288 per night (USD)

    Expedia

    Anchorage 406 in Siesta Key

    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 $288 per night (USD)

    Expedia

    Details
  • Anchorage 507 in Siesta Key
    From $307 per night (USD)

    VRBO

    Anchorage 507 in Siesta Key

    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 $307 per night (USD)

    VRBO

    Details
  • Anchorage 405 in Siesta Key
    From $288 per night (USD)

    Expedia

    Anchorage 405 in Siesta Key

    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 $288 per night (USD)

    Expedia

    Details
  • Anchorage 704 in Siesta Key
    From $327 per night (USD)

    VRBO

    Anchorage 704 in Siesta Key

    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 $327 per night (USD)

    VRBO

    Details
  • Anchorage 403 in Siesta Key
    From $307 per night (USD)

    Expedia

    Anchorage 403 in Siesta Key

    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 $307 per night (USD)

    Expedia

    Details
  • Anchorage 807 in Siesta Key
    From $327 per night (USD)

    VRBO

    Anchorage 807 in Siesta Key

    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 squ ...

    From $327 per night (USD)

    VRBO

    Details
  • Anchorage 711 in Siesta Key
    From $518 per night (USD)

    Expedia

    Anchorage 711 in Siesta Key

    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 $518 per night (USD)

    Expedia

    Details
  • Anchorage PH-6 in Siesta Key
    From $327 per night (USD)

    VRBO

    Anchorage PH-6 in Siesta Key

    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 st ...

    From $327 per night (USD)

    VRBO

    Details
  • Crystal Sands Tower Unit 706 - Beachfront
    From $426 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 $426 per night (USD)

    Expedia

    Details
  • Modern & Cozy Home, close to beach & Dearborn St!
    From $201 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 $201 per night (USD)

    VRBO

    Details
  • Centrally located!  6 miles to Siesta and St. Armands. 2 miles to downtown.
    From $238 per night (USD)

    Expedia

    Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    After a day of exploring the local sites, sit back and relax on the patio with a beverage and enjoy the beautiful weathe ...

    From $238 per night (USD)

    Expedia

    Details
  • Resort-style amenities at Harbor Towers | Walk to Siesta Key Beach | Views of the Bay!
    From $140 per night (USD)

    VRBO

    Resort-style amenities at Harbor Towers | Walk to Siesta Key Beach | Views of the Bay!

    Bedrooms:
    1
    Bathrooms:
    1
    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 $140 per night (USD)

    VRBO

    Details
  • Private Beach 1 Block To Lido Beach. 1/2 Mile  St. Armand Circle
    From $424 per night (USD)

    Expedia

    Private Beach 1 Block To Lido Beach. 1/2 Mile St. Armand Circle

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Many Five Star reviews on this bright & sunny beach home with two bedrooms, 2 baths, very private, fenced yard, hardwood ...

    From $424 per night (USD)

    Expedia

    Details
  • Corner unit, water views, boat access, remodeled, elevator building, no pets
    From $218 per night (USD)

    VRBO

    Corner unit, water views, boat access, remodeled, elevator building, no pets

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Breathtaking, panoramic views await you at this luxurious condo on the 7th floor of an elevator building overlooking the ...

    From $218 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 $154 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 $154 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 $622 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 $622 per night (USD)

    VRBO

    Details
  • Sun, Sand and Savings Sarasota Deals
    From $257 per night (USD)

    Expedia

    Sun, Sand and Savings Sarasota Deals

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

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

    From $257 per night (USD)

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    Details
  • Beach front paradise located in a Condo Building Beach front Penthouse!
    From $631 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 $631 per night (USD)

    VRBO

    Details
  • Pool Home, Steps to Secluded Beach Access
    From $285 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 $285 per night (USD)

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    Details
  • A Bayside Treasure - Outstanding Waterfront Views!!
    From $232 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 $232 per night (USD)

    VRBO

    Details
  • Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook
    From $2048 per night (USD)

    Expedia

    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 $2048 per night (USD)

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    Details
  • Spacious & Quiet at Fishermans Haven on Siesta Key. Private Beach, Heated Pool, Fish on the Bay. FH6
    From $218 per night (USD)

    VRBO

    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 $218 per night (USD)

    VRBO

    Details
  • Beautiful one bedroom condo on Siesta Key.  minutes from Siesta key Beach!
    From $164 per night (USD)

    Expedia

    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 $164 per night (USD)

    Expedia

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

    VRBO

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

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Updated and charming cottage RIGHT ON THE BEACH where you can sunbathe, swim, snorkel, collect shells and sharks' teeth, ...

    From $397 per night (USD)

    VRBO

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

    Expedia

    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)

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    Details
  • Upscale Hidden Jewel 2 miles to Nokomis Beach!
    From $320 per night (USD)

    VRBO

    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 $320 per night (USD)

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • Anchorage 208 in Siesta Key
    From $288 per night (USD)

    VRBO

    Anchorage 208 in Siesta Key

    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 $288 per night (USD)

    VRBO

    Details
  • Anchorage 207 in Siesta Key
    From $288 per night (USD)

    Expedia

    Anchorage 207 in Siesta Key

    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 $288 per night (USD)

    Expedia

    Details
  • Charming Private Garden Cottage hide away in the heart of Sarasota
    From $124 per night (USD)

    VRBO

    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 $124 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
  • Family friendly, Siesta Key.
    From $228 per night (USD)

    VRBO

    Family friendly, Siesta Key.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Our home is 1/2 mile from Siesta Key Beach access. It is ideal for an extended getaway, or a family who needs a place wh ...

    From $228 per night (USD)

    VRBO

    Details
  • Ventana Rosa | Beautiful Sarasota Home Near Siesta Key w/ Private Pool & Large Outdoor Space
    From $359 per night (USD)

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Experience the Ultimate in Luxury at Ventana Rosa – Your Siesta Key Escape Discover the essence of luxury and tranquili ...

    From $359 per night (USD)

    Expedia

    Details
  • “Casa Concord: 3BR-2BA Home with Private SaltH20 Pool, 2 Miles from Siesta Key”
    From $327 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 $327 per night (USD)

    VRBO

    Details
  • Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach
    From $326 per night (USD)

    Expedia

    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 $326 per night (USD)

    Expedia

    Details
  •  amazing apartment on the beach. With  warm pool .
    From $117 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 $117 per night (USD)

    VRBO

    Details
  • Relax`n - Beautiful newer South Venice home with pool and spa
    From $260 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 $260 per night (USD)

    Expedia

    Details
  • Beautiful 2022 renovated - 550 Sq Ft  Patio - across street from beach
    From $335 per night (USD)

    VRBO

    Beautiful 2022 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 $335 per night (USD)

    VRBO

    Details
  • Longboat Key Escape–2BR Beachplace Condo Near the Ocean Unit 5-301 by RVA
    From $706 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 $706 per night (USD)

    Expedia

    Details
  • Venice Pool Home- Breezy Inn
    From $333 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 $333 per night (USD)

    VRBO

    Details
  • Casa Blanca Villa A11
    From $286 per night (USD)

    Expedia

    Casa Blanca Villa A11

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Non smoking villa and lanai. Enjoy your beach vacation in this beautiful large 2 bedroom, 2 bathroom private villa. Lo ...

    From $286 per night (USD)

    Expedia

    Details
  • Casa Blanca Villa A02
    From $396 per night (USD)

    VRBO

    Casa Blanca Villa A02

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Casa Blanca Beach Resort includes Gulf-front Apartments and Private Villas. Each villa and apartment are individually ow ...

    From $396 per night (USD)

    VRBO

    Details
  • Casa Blanca Villa C18
    From $303 per night (USD)

    Expedia

    Casa Blanca Villa C18

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to one of the largest 2 Bedroom/2 Bath Villas in Casa Blanca -- and the only one with a glimpse of the gulf! En ...

    From $303 per night (USD)

    Expedia

    Details
  • Casa Blanca Villa C07
    From $274 per night (USD)

    VRBO

    Casa Blanca Villa C07

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Casa Blanca Beach Resort includes Gulf-front Apartments and Private Villas. Each villa and apartment are individually ow ...

    From $274 per night (USD)

    VRBO

    Details
  • Casa Blanca Villa A15
    From $406 per night (USD)

    Expedia

    Casa Blanca Villa A15

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 bdrm. 2 bath/Sleeps 6 A-15 Property Information: Large 2 bedroom 2 bath villa located a few steps from our private bea ...

    From $406 per night (USD)

    Expedia

    Details
  • Casa Blanca Villa B18
    From $292 per night (USD)

    VRBO

    Casa Blanca Villa B18

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This villa is one of the large villas and closest to the beach area. It has a 55 inch Samsung plasma TV and a blue ray ...

    From $292 per night (USD)

    VRBO

    Details
  • Casa Blanca Villa C13
    From $274 per night (USD)

    Expedia

    Casa Blanca Villa C13

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome! Villa C13 is a beautiful 2 bedroom, 2 bath beach accommodation located in the exclusive Casa Blanca beachside c ...

    From $274 per night (USD)

    Expedia

    Details
  • Casa Blanca Villa C08
    From $274 per night (USD)

    VRBO

    Casa Blanca Villa C08

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Casa Blanca Beach Resort includes Gulf-front Apartments and Private Villas. Each villa and apartment are individually ow ...

    From $274 per night (USD)

    VRBO

    Details
  • 103 Gulf Front Apartment
    From $347 per night (USD)

    Expedia

    103 Gulf Front Apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy unobstructed views of the Gulf of Mexico and the white sand of Siesta Key Beach from the 1st floor of this tastefu ...

    From $347 per night (USD)

    Expedia

    Details
  • Harbor Towers- 2Bed/2 Bath, Your Own Private Entrance!
    From $226 per night (USD)

    VRBO

    Harbor Towers- 2Bed/2 Bath, Your Own Private Entrance!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Resort-style Siesta Key living is finally within your reach! Close to the #1 rated beach year after year! Beautiful fur ...

    From $226 per night (USD)

    VRBO

    Details
  • 3/3 Newly Upgraded and Spacious Modern Unit ~ Harbor Towers Yacht & Racquet Club
    From $380 per night (USD)

    Expedia

    3/3 Newly Upgraded and Spacious Modern Unit ~ Harbor Towers Yacht & Racquet Club

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    You are in the heart of Siesta Key - one of the most popular destinations in America due to its powdery white quartz-cry ...

    From $380 per night (USD)

    Expedia

    Details
  • Hotel Studio (Ground Level) - Unit C
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    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 ...

    Click For Pricing

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  • Hotel Studio (Ground Level) - Unit B
    From $247 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 $247 per night (USD)

    Expedia

    Details
  • Escape Casey Key Hotel & Marina - 1 Bed 1 Bath  K Bed Villa 4b
    Click For Pricing

    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 ...

    Click For Pricing

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  • 2 Bedroom/1 Bath Villa (Ground Level) - Unit 5
    From $320 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 $320 per night (USD)

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    Details
  • 2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A
    From $365 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 $365 per night (USD)

    VRBO

    Details
  • 1 Bedroom/1 Bath Villa (Ground Level) - Unit 9
    Click For Pricing

    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 ...

    Click For Pricing

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    Details