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.

 

 

Siesta Jewel

3 Bedrooms • 4 Baths (3 full, 1 half) • Sleeps 5-10
Internet Near Ocean Private Pool
Steps from Siesta Key Beach, this beautifully renovated 3-bedroom, 3.5-bath home offers sophisticated coastal-inspired decor. The master suite has a private screened balcony overlooking the pool with an egg chair swing. A screened patio includes bar seating, a dining area, and a cozy lounge. The first-floor mudroom has a shower for easy beach cleanup. With its classic beach cottage feel and modern amenities, this home is the perfect coastal retreat. Book now!

Photos Details Inquire

Our Happy Place

3 Bedrooms • 3 Baths • Sleeps 3-6
Allows pets Accessible Internet Water View Hot Tub
Welcome to "Our Happy Place," a charming 3-bedroom, 3-bathroom condo in Margaritaville - One Particular Harbor in Harbour Isles condo complex. Enjoy a fully stocked kitchen with an island and bar seating, a dining area for six, and a cozy living room. The condo offers a screen-enclosed balcony with nature and lake views, remote control ceiling fans, and access to community amenities including a pool, splash pad, bar, loungers, grills, and scenic trails.

Photos Details Inquire

Siesta Sand Castle

4 Bedrooms • 3 Baths • Sleeps 8-10
Allows pets 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!

Photos Details Inquire

Siesta Sea Walk

3 Bedrooms • 2 Baths • Sleeps 3-6
Internet Near Ocean
Steps from Siesta Key Beach, this 3-bedroom, 2-bath retreat by Pink Pineapple Properties is perfect for your dream vacation. Bright, coastal interiors, a fully equipped kitchen, and serene bedrooms ensure comfort. Relax on the screened porch, enjoy the private backyard with outdoor shower, or explore nearby Siesta Key Village. Outfitted with all essentials for a seamless stay, this home is ideal for family trips, romantic getaways, or group escapes. Book today!

Photos Details Inquire

The Turquoise Turtle

2 Bedrooms • 2 Baths • Sleeps 3-5
Allows pets Internet Private Pool

Introducing The Turquoise Turtle, your charming sanctuary in Sarasota's paradise. Nestled in the heart of Gulf Gate, this cozy short-term rental offers a tranquil escape with coastal-inspired décor and modern amenities. Relax in style with a fully equipped kitchen, private patio with heated pool and hot tub, and serene garden. Located near Sarasota's top attractions, including pristine beaches and vibrant downtown shops, The Turquoise Turtle is the perfect retreat for your next getaway.

Photos Details Inquire

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.

Photos Details Inquire

Salty Unicorn

2 Bedrooms • 2 Baths • Sleeps 4-6
Allows pets 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.

Photos Details Inquire

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.

Photos Details Inquire

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!

Photos Details Inquire

Calm Waters Cottage

2 Bedrooms • 1 Bath • Sleeps 2-4
Allows pets Internet Near Ocean
"Welcome to Calm Waters Cottage, a charming bungalow just minutes from Siesta Key Beach! Enjoy spacious living, a fully equipped kitchen, and comfy beds. No cable, but smart TVs for streaming. Book now for a perfect beach getaway!"

Photos Details Inquire

Key Lime Surf Shack

2 Bedrooms • 1 Bath • Sleeps 1-5
Allows pets Internet
Welcome to Key Lime Surf Shack, a delightful beach themed bungalow mere minutes from Siesta Key Beach! Revel in ample living space, a well-equipped kitchen, and cozy sleeping quarters. Secure your spot now for an unforgettable beach escape!

Photos Details Inquire

The Pink Palm

2 Bedrooms • 1 Bath • Sleeps 2-4
Allows pets 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.

Photos Details Inquire

Sandy Starfish

2 Bedrooms • 1 Bath • Sleeps 1-4
Allows pets 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.

Photos Details Inquire

Sarasota Sunrise

2 Bedrooms • 1 Bath • Sleeps 1-5
Allows pets Internet
Experience comfort and style in this two-bedroom, one-bathroom retreat. Enjoy a cozy living room with a smart TV and a convenient desk area. The fully stocked kitchen includes an oven, stove, refrigerator, dishwasher, microwave, coffee maker, and toaster. Both bedrooms feature queen beds. Just a short walk to Gillespie Park's tennis, basketball, and playground facilities. Book your stay today!

Photos Details Inquire

Siesta Sunset

2 Bedrooms • 1 Bath • Sleeps 2-5
Allows pets Internet
Discover Siesta Sunset, a charming two-bedroom, one-bathroom unit just minutes from downtown Sarasota and the stunning Siesta Key Beach. This duplex features a spacious, inviting living area and a large outdoor sitting space with a cornhole game. Enjoy the convenience of being close to vibrant city life, exquisite dining, and shopping, while only a short drive from the beautiful beaches of Siesta Key. Perfect for a relaxing getaway with family or friends!

Photos Details Inquire

 

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.

 

 

All photography by:

Dylan Jon Wade Cox

www.djwcphoto