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.

 

 

$450-650/night

The Hollywood House

4 Bedrooms • 3.5 Bathrooms • Sleeps 9-13
Internet Near Ocean Private Pool

🍍Pink Pineapple Properties🍍 proudly presents: "The Hollywood House"- the quintessential family friendly vacation home located across from the intercoastal waterway and minutes from world famous Siesta Key!

Relax and unwind in this luxurious 2600 sq. ft. "Old Florida" home where every detail has been thoughtfully curated with a designer touch.

The tropical oasis in the back yard is the icing on the cake and includes a huge heated salt water pool, Fire pit, al fresco dining, a spacious covered lanai, hammocks, and much more!

Perfect for a family reunion, wedding, getaway with friends, or retreat, Hollywood House comfortably accommodates 13 guests.

Each space has been carefully curated with an “old Florida” vibe mixed with a mid-century twist, utilizing a mix of local vintage rattan furnishings, local art and accessories along with a selection of comfortable furnishings accented with unique designer touches.

Take the perfect Insta photo in the lucite "egg chair", enjoy your favorite beach read in the comfy hammock or hanging swing chair, float aimlessly in the saltwater pool or enjoy a family BBQ dinner on the the covered lanai, the possibilities are endless.

If you are a sun lover, head upstairs to the sun deck and soak up the afternoon heat, then cool off in the pool or walk to Siesta Key for a dip in the gulf.

Does your family love games? We have stocked the home with all of the classics and there are plenty of places to spread out and play!
Kids love the outdoor checkers/chess games, swinging on the huge outdoor egg chair, and exploring the hidden niches throughout the grounds.

Take some time to yourself and relax in the spectacular claw-foot soaking tub, then wrap up in a luxury Egyptian cotton oversized bath towel to complete the spa experience. You will get the best sleep of your life as you drift off on luxury Purple brand mattresses and pillows and linens. Stroll outside using your private lanai entrance and enjoy your morning coffee overlooking the lush gardens and pool.

We are available to guests throughout their stay. We live super close and are here to help with anything.

Situated just East of the Stickney Point bridge, this is the perfect location to get away from the hustle and bustle of the island. Walk, or rent a bike and ride to beach access 12 for quick convenient beach access.

Walk, ride bikes or drive to beaches, shopping, and restaurants. Catch the trolley on Siesta to take you to the Village for afternoon cocktails or to catch some live music.

 

 

Welcome to "The Hollywood House"- the quintessential family friendly vacation home located across from the intercoastal waterway and minutes from world famous Siesta Key!

Relax and unwind in this luxurious 2600 sq. ft. "Old Florida" home where every detail has been thoughtfully curated with a designer touch.

The tropical oasis in the back yard is the icing on the cake and includes a huge heated salt water pool, Fire pit, al fresco dining, a spacious covered lanai, hammocks, and much more!

Perfect for a family reunion, wedding, getaway with friends, or retreat, Hollywood House comfortably accommodates 13 guests.

Each space has been carefully curated with an “old Florida” vibe mixed with a mid-century twist, utilizing a mix of local vintage rattan furnishings, local art and accessories along with a selection of comfortable furnishings accented with unique designer touches.

Photos Details Inquire


$200-550/night

The Salty Mermaid

3 Bedrooms • 2 Bathrooms • Sleeps 4-6
Internet Near Ocean

🍍🍍Pink Pineapple Properties🍍🍍Proudly presents: The Salty Mermaid! 🧜🏻‍♀️


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!

When you stay in this perfectly appointed luxury property you are surrounded by inspiring and curated local art that beautifully reflects the charm and vibe of this amazing city.

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 or game night. Enjoy the super comfy sectional and the huge smart TV and put your feet up after a long day at the beach!

The master bedroom has a luxurious king bed, a large closet, and a TV for extra relaxation. The second bedroom has a comfy queen bed, a spacious closet and lots of extra storage. The third bedroom has two twin beds and a large closet for storage.  The kitchen has everything you will need. A stainless steel oven, fridge, microwave and dishwasher to make your vacation even easier. You have a beautiful view of the expansive back yard from the kitchen sink. There are two bathrooms one with a tub/shower combo and the other with a standard shower. Each bathroom is equipped with plenty of fluffy towels and travel size bath products.  For your convenience, there is also a full size washer and dryer available on the property. 

☀️☀️Every detail has been professionally thought out. From the ultra cozy sectional, the high end mattresses and linens, to the completely stocked kitchen with everything needed for family dinner, you will feel the attention to detail and immediately feel relaxed and recharged.



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$200-550/night

The Funky Fish House

2 Bedrooms • 2 Bathrooms • Sleeps 3-5
Internet Near Ocean

🍍🍍Pink Pineapple Properties🍍🍍
Proudly presents: The Funky Fish House! 🐠🐟
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!

When you stay in this perfectly appointed luxury property you are surrounded by inspiring and curated local art that beautifully reflects the charm and vibe of this amazing city.

This one-of-a-kind property features brand new stainless steel appliances, A/C, full size washer and dryer, free Wi-Fi, and is even set up with beach towels, beach chairs, and fine linens.🏝☀️

☀️☀️Every detail has been professionally thought out. From the ultra cozy sectional, the high end mattresses and linens, to the completely stocked kitchen with everything needed for family dinner, you will feel the attention to detail and immediately feel relaxed and recharged.

 

 

Plan for a fun vacation getaway at The Funky Fish House! This Newly renovated and artfully adorned home is located minutes to Siesta Key and downtown Sarasota.  An array of whimsical handcrafted fish, buoys, driftwood and art will delight the senses as you step into this clean and thoughtfully designed beach bungalow.

This one-of-a-kind property features brand new stainless steel appliances, A/C, full size washer and dryer, free Wi-Fi, and is even set up with beach towels, beach chairs, and fine linens. Every detail has been professionally thought out. From the ultra cozy sectional, the high end mattresses and linens, to the completely stocked kitchen with everything needed for family dinner, you will feel the attention to detail and immediately feel relaxed and recharged.

Grab your morning coffee from the coffee bar and head to your private deck to enjoy a quiet morning with nature, then head to the the number one beach in the country for a fun day in the sun! 

 

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$200-550/night

The Salty Unicorn

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

🍍🍍Pink Pineapple Properties🍍🍍

proudly presents The Salty Unicorn, only five miles to beautiful SIESTA KEY!!

Step into this completely remodeled, designer home close to everything Sarasota has to offer. Take an easy five minute 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.

The home boasts a large living area perfect for family movie night or game night. Enjoy the super comfy sectional and the huge smart TV and put your feet up after a long day at the beach!
The Outdoor area is my favorite part of the house. There is a huge (Un-heated) pool equipped with tons of pool toys. The large lanai boats four comfy lounge chairs, a dining table that seats four and a new grill. This is the perfect place to spend afternoons after a morning at the beach!
The master bedroom has a luxurious king bed, a large closet, and a TV for extra relaxation. A ceiling fan tops this room off for a cool comfortable rest.

The second bedroom has a comfy queen bed, a spacious closet and lots of extra storage. This room also has a ceiling fan to keep you cool at night.

There is a third room perfect for the kids or relaxing on the daybed with a book while enjoying the thoughtful touches on the mid-century room divider! This room has a twin day bed and a pull out twin bed. There is a small dresser perfect for storage and an amazing curated book shelf for you to enjoy. The second bathroom is connected to this room.
On the other side of the seaside room divider is the large dining room. This room boasts large sliding glass doors that lead right to the sparkling pool. The trendy dining table seats six and is perfect for a family dinner. If you like a pool view while you read, cozy up in the rocking chair in the corner of this room.

The kitchen has everything you will need. A stainless steel oven, fridge and dishwasher make your vacation even easier. A cute little mid-century microwave to top it off! You have a beautiful view of the expansive back yard and pool from the kitchen sink.

There are two bathrooms one with a tub/shower combo and the other with a standard shower. Each bathroom is equipped with plenty of fluffy towels and bath products.
For your convenience, there is also a washer and dryer available on the property.

The SMART TV's do not have cable! Please use your personal Netflix, Hulu, Sling, etc. to watch your favorite shows and movies.

I will provide you with a Personalized access code a few days prior to arrival.

We live super close to the property and are available for anything you need during your stay.

We love this property because of its proximity to the beach and downtown Sarasota. The location is fabulous! So close to everything you could need. We also love the huge un-heated pool and huge backyard yard. It's a fun, quirky cottage I know you will have a blast at!

The pool is open year-round and is not heated. It feels great to cool off after a morning at the hot beach. 🍍🍍

 

 

 

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$133-232/night

The Palm & Pine

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

Welcome to The Palm & Pine! This completely renovated bungalow in the beautiful Arlington Park neighborhood 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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3 Bedrooms • 3.5 Bathrooms • Sleeps 3-8
Internet Fireplace Near Ocean Private Pool Hot Tub

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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.