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
Sandy Bottoms Beach House- The ideal beach home with a private heated pool
 
Step into this luxury beachfront property and experience beach living at its finest. Hop out of your beautiful heated pool and stroll down your private path and right into the warm gulf of Mexico to watch the most beautiful sunset of your life. 
 

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$650-1,500/night

Siesta Sand Castle

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

This newly remodeled, Siesta Key three-story, family home, just minutes to the #1 beach in the USA Siesta Key village, is ready to welcome you and your family to Paradise!

Step into this updated designer home close to everything Siesta Key has to offer. The home boasts several large living areas perfect for family movie night, a garage packed full of beach toys, comfy bedrooms, a well equipped chefs kitchen, four large bedrooms, an extra large lanai and much much more! 

 

 

 

 

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2 Bedrooms • 2 Baths • Sleeps 1-5
Internet

Step into this completely remodeled, designer home in the historic McClellan Park neighborhood close to everything Sarasota has to offer. Take a quick ride over to the North Bridge and make your way onto one of the most beautiful beaches in the country or stay home and relax while enjoying a glass on the private secluded deck. Walk or rent a bike and explore the boutiques, bars and amazing restaurants in the Southside Village and stop in for a scoop of ice-cream before heading home. 

 

 

 

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$295-550/night

Osprey Oasis

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

This unique home is located on a private street away from the hustle and bustle of the city, yet close to the action. As you pull up to this wooded oasis you will notice the natural vegetation that gives complete privacy to this newly renovated home where every detail has been thought of for the perfect vacation.  The cool coastal vibe is sure to impress even the most discerning guests.  

 

 

 

 

 

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$275-500/night

Casa del Sol

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

This newly remodeled single family bungalow, just minutes to the #1 beach in the USA and downtown Sarasota, is ready to welcome you and your family to Paradise!

Step into this completely remodeled designer home close to everything Sarasota has to offer. The home boasts a large living area perfect for family movie night, a fun game room equipped with our favorite family board games, three large bedrooms, a large screened lanai and much much more!

 

 

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$225-550/night

Salty Unicorn

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

Step into this completely remodeled, designer home close to everything Sarasota has to offer. Take an easy five mile car ride to one of the most beautiful beaches in the country or stay home and relax while enjoying a glass of wine on the screened in lanai and cool off in the over sized private pool. The spacious back yard provides plenty of room for family games or sunbathing.

 

 

 

 

 

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$125-450/night

The Pink Palm

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

The Pink palm- Designer cottage close to everything Sarasota has to offer and walking distance to Siesta Key 

This newly decorated, two-bedroom bungalow duplex, just steps away from the #1 beach in the USA, Siesta Key, is ready to welcome you and your family to Paradise!  Take an easy 15 minute stroll to one of the most beautiful beaches in the country or stay home and relax while enjoying a glass of wine on the covered front porch. 

 

 

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$125-450/night

Sandy Starfish

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

The Sandy Starfish- Designer home close to everything Sarasota has to offer and walking distance to Siesta Key 


This newly decorated, two-bedroom duplex-bungalow, just steps away from the #1 beach in the USA, Siesta Key, is ready to welcome you and your family to Paradise!  Take an easy 15 minute stroll to one of the most beautiful beaches in the country or stay home and relax while enjoying a glass of wine on the covered front porch. 

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$134-309/night

Palm & Pine

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

The home is  located a short distance from all the best of Sarasota. Near shops/restaurants in Southside Village, downtown, and Pinecraft (a quaint Amish village) . Only 5 miles to Siesta Key and Lido Key! Our home is outfitted with everything you need for a relaxing beach getaway or escape from winter: a chef's kitchen, ultra high-speed Wi-Fi (great for digital nomads), and amazing screened lanai!

 

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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.