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Sarasota Vacation Rentals with Boat Dock

(12 rentals)
Sarasota Villa
Sleeps 5, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Discover your own little piece of paradise in this beautifully remodeled 2-bedroom, 2-bathroom villa located in the heart of Siesta Key, where contemporary amenities and a prime location combine for an unforgettable vacation experience. Taken down to the studs in 2025, this villa has been completely upgraded...

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Featured review

"This quiet and adorable Villa was perfect for our family!"

This quiet and adorable Villa was perfect for our family! It was clean, comfortable and super close to the beach. The washer and dryer were a lifesaver with kids and all their wet towels/clothes. Easy after...

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$380
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms
4 reviews

Distance to beach: 0.5 miles to Siesta Key Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Recently Remodeled Luxury Waterfront Condo – Perfect Couples’ GetawayEnjoy the ultimate Siesta Key escape in this beautifully remodeled waterfront condo, complete with a private boat dock and slip for boats or jet skis. Ideally located, you can walk to the beach, village shops, top-rated...

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Featured review

"Incredible stay!! 10 stars out of 5."

Beautifully decorated condo in prime location. Extra clean and upscale. Best location on the harbor with water views and walking distance across the bridge onto Siesta Key's Tiki Bar. Owner is a pleasure...

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$331
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms
1 review

Distance to beach: 0.5 miles to Siesta Key

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Recently Redecorated Luxury Waterfront Condo – Perfect Couples’ GetawayEnjoy the ultimate Siesta Key escape in this beautifully decorated waterfront condo, complete with a private boat dock and slip for boats or jet skis. Ideally located, you can walk to the beach, village shops, top-rated...

View all property information

Featured review

"Comfortable Condo"

This is such a comfortable, well decorated and fully equipped condo. The location was very quiet with nice views and in a great location for accessing the beach and siesta key. You can easily bike to siesta...

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$318
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 0.5 miles to Siesta Key

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Luxury Waterfront Condo for a Perfect Couples Getaway Private Boat Dock and Slip for Boat or Jet SkisEnjoy the ultimate coastal escape in this stunning waterfront condo, ideally located within walking distance to the beach, charming town center, boutique shopping, top rated restaurants, live music,...

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$297
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 0.5 miles to Siesta Key Crescent Beach Access 12

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This newly decorated luxury condominium is located in The Boatyard, a highly sought after, gated community on the intracoastal. It is within walking distance to gorgeous Siesta Key Crescent Beach, many water sport activities, shopping, restaurants and more. Private boat slips are also available, right...

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$217
avg per night

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Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This newly decorated luxury condominium is located in The Boatyard, a highly sought after, gated community on the intracoastal. It is within walking distance to gorgeous Siesta Key Crescent Beach, many water sport activities, shopping, restaurants and more. Private boat slips are also available, right...

View all property information

$333
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Enjoy Gulf sunsets and the sounds of the surf from your 2nd floor beachfront condo - just one flight of steps - or use the elevator. Unit A205 offers the perfect place to enjoy the sea and sky from sunrise to sunset! On the Gulf side, a spacious lanai offers an unobstructed 180 degree view. Watch as...

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$368
avg per night
Sarasota House
Sleeps 4, 2 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

To view complete details callThis home is a beautiful waterfront beach bungalow located on Little Sarasota Bay on the desirable and less congested location of South Siesta Key, Sarasota FL. This sanctuary is within walking distance of the public amenities of Turtle Beach, the Tiki Hut Pub, Bayfront...

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Featured review

"Perfect getaway!"

This house and grounds were AMAZING! The decks, dock, and gliders were relaxing and quiet-we enjoyed the bird watching and saw dolphins on our last day! Turtle Beach is nice-not quite Siesta Key sand,...

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$372
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 1 bathroom
12 reviews

Distance to beach: 0.5 miles to Turtle Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Looking for the perfect vacation rental? Weekly? Monthly? or for the Season? This 2 bed /1 bath 3rd floor condo has just been freshly painted with a brand new kitchen and new flooring. Features a queen size bed in one room & a KING in the other room. Large granite island in the fully equip kitchen...

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Featured review

"The Perfect Vacation"

We just finished a week stay at this beautiful condo. Location is perfect, the view from the balcony shows the pool, river, and ocean. Condo was very clean and was the perfect size. The kitchen island and...

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$214
avg per night
Sarasota House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Beautifully renovated and immaculate home with pool and dock Near St Armand's and Lido BeachNEW PROPERTYWelcome to 440 Cleveland Drive, a stunning, fully renovated rental property on Lido Key where luxury meets coastal charm. Completed in March 2025, everything inside and outside this home...

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$1,605
avg per night
Sarasota House
Sleeps 8, 4 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 0.1 miles to Lido

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

St. Armand's Canal-Front Pool Home steps to the beach!This gem, ranch style home estate has been completely rebuilt and remodeled in 2015 from the frame including all new finishes inside and out. With fresh, coastal Old-Florida decor, it is in one of the most desirable locations on the west...

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$1,124
avg per night
Sarasota House
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 1 miles to Longboat Key

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of dishware, gadgets, cooking equipment for...

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$379
avg per night
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