When you book a vacation with Pink Pineapple Properties, you know you are getting a beautifully decorated and well-maintained property that has been carefully curated and designed using local artwork and décor. 
Every detail is important to us and each decision is made with you, the guest, in mind. 

We look forward to showing you why we are consistently ranked as one of the top vacation rental companies in the Sarasota Florida area.

 

 

$650-1,500/night

Sandy Bottoms Beach House

3 Bedrooms • 4 Baths (3 full, 1 half) • Sleeps 2-6
Internet Fireplace Oceanfront Private Pool

Beachfront house with private heated pool

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$650-1,500/night

Siesta Sand Castle

4 Bedrooms • 3 Baths • Sleeps 8-10
Internet Beach View Private Pool

Stunning Siesta Key home close to the Village and Beach!

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2 Bedrooms • 2 Baths • Sleeps 1-5
Internet

Historic West of Trial Home- Walk to Shops and Restaurants

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$295-550/night

Osprey Oasis

3 Bedrooms • 2 Baths • Sleeps 2-6
Internet Private Pool

Private Oasis with heated pool near beaches

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$275-500/night

Casa del Sol

3 Bedrooms • 2 Baths • Sleeps 1-7
Internet Fireplace Near Ocean

Designer inspired 3 bedroom home close to beaches and downtown

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$225-550/night

Salty Unicorn

2 Bedrooms • 2 Baths • Sleeps 4-6
Internet Private Pool

 

 

 

 

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$125-450/night

The Pink Palm

2 Bedrooms • 1 Bath • Sleeps 2-4
Internet Near Ocean

Charming 2 Bedroom Walking Distance to Beach

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$125-450/night

Sandy Starfish

2 Bedrooms • 1 Bath • Sleeps 1-4
Internet Near Ocean

Charming 2 Bedroom Walking Distance to Beach

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$134-309/night

Palm & Pine

2 Bedrooms • 1 Bath • Sleeps 3-4
Allows pets Internet Near Ocean

 

 

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The team at Pink Pineapple Properties treats every guest like family!  We want your vacation in Sarasota to be the most enjoyable, laid back trip you have ever experienced, from the moment you walk in the front door you will feel at home. Unwind with a glass of wine as the backyard oasis draws you in and start your relaxing vacation before you even unpack.