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Caribbean Dream

Luxury Condo on Siesta Key w/ Heated Pool, Walking Distance to Beach & Village!

Bedrooms: 2

Bathrooms: 2 Full

Sleeps: 7

Imagine the refreshing dip in your semi-private heated pool after a sunny day, a relaxing soak in the whirlpool or just lounging on one of the chaises enjoying the sun.

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Exclusive Amenities Include: ↑↓

• Semi-Private, HOA-Maintained Heated Pool & Spa with Poolside Dining & Lounge Space
• 2 Balconies with Dining & Lounge Areas & Multiple Balcony Views
• Located in Siesta Key Village – Just a 2-Minute Walk to Siesta Key Beach
• 2 Bedrooms, 2 Full Baths, Sleeps 7: 1 King Bed, 1 Queen Bed, Twin Sleeper Chair & Queen Sleeper Sofa – Linens Provided
• Private Garage & Gated Entrance
• Free Wi-Fi & 3 HDTVs
• Gas Grill & Convenience Elevator for Luggage, Groceries, and Gear
• Regular & Keurig Coffee Makers, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided
• Starter Pack of Toiletry Essentials: Shampoo, Conditioner, Hand/Face Soap, Body Lotion, & Makeup Wipes
• Starter Pack of Home Essentials: Dish Soap, Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipes
• Beach Towels, Chairs, Cooler, & Caddy Provided
• Enhanced Cleaning Protocols by Our CottageClean Team

Overview ↑↓

Caribbean Dream | Heated Pool, Balconies & Walk to Siesta Key Beach & Village

Why You’ll Love This Home
Awaken to tropical breezes and the promise of a Siesta Key day at Caribbean Dream, where the vibrant energy of Siesta Key Village meets the serene beauty of the beach, all just steps from your door. This condo is a sun-drenched oasis designed for memorable getaways.

‍‍ Perfect For
Ideal for families, couples, or small groups seeking a harmonious blend of beach access, village charm, and tranquil living.

️ Imagine This
Start your day sipping coffee on one of your private balconies, listening to the gentle rustle of palms. After a leisurely breakfast prepared in your gourmet-grade kitchen, grab the provided beach gear and stroll just two minutes to sink your toes into Siesta Key’s renowned quartz sands. Spend your afternoon splashing in the Gulf, building sandcastles, or simply unwinding under the sun. Return to your serene retreat for a refreshing dip in the semi-private heated pool and spa, then fire up the gas grill for an alfresco dinner by the poolside. As evening approaches, take a short walk into Siesta Key Village to explore local boutiques, enjoy fresh seafood at a charming restaurant, or discover live music. End your perfect day back on the balcony, watching the sunset paint the sky with vibrant hues.

Where You’ll Sleep
Bedroom 1: King Bed and Twin Sleeper Chair, ensuite bathroom, 2nd floor, balcony access, TV
Bedroom 2: Queen Bed, shared bathroom, 2nd floor, TV
Common Space: Queen Sleeper Sofa, 2nd floor, TV

Explore the Area
Experience the best of Siesta Key from your prime location.
Enjoy a quick 0.1-mile walk to Siesta Key Beach, renowned for its powdery sands and crystal-clear waters.
Just 0.1 miles to Siesta Key Village, immerse yourself in the lively coastal energy with an array of dining options, charming boutiques, and vibrant nightlife right at your fingertips.

Need to Know ↑↓

Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection. This home is part of a condo unit, sharing common walls, floors, ceilings, and outdoor spaces with other units. When renting Caribbean Dream, you will have access to the 1st and 2nd floors of the building, the leftmost garage, and shared outdoor and pool areas. Starter packs of kitchen and toiletry essentials are provided for a seamless first couple of nights. Free High-Speed WiFi is available. This pool is heated between November 15 - April 15. This home has stairs; if any guest has difficulty with stairs, please contact us for alternative accommodations. Per HOA requirements, garages can fit a vehicle no bigger than 72 inches in height, and guest vehicle height will be needed before arrival. Grills may only be used on the ground level, pulled 10 feet from the building. No grills, hibachi, or any open flame cooking device or fire pit may be used on balconies or patios.

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Reviews ↑↓

Total reviews: 21

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Review Date: July 21, 2026

"We loved our stay! Everything we needed was provided, the place was very clean and comfortable!

Reviewed By: Marcy

Response from The Cottages on the Key:
Hi Marcy, Thank you so much for your wonderful review! We’re thrilled to hear you loved your stay and found the home to be clean, comfortable, and well-equipped with everything you needed. Creating a welcoming space where guests can simply arrive, settle in, and enjoy their vacation is exactly what we strive for. Your kind words truly mean a lot to our team. Thank you for choosing to stay with us. We truly appreciate your feedback and hope to have the pleasure of welcoming you back for another memorable getaway! Warm regards, Guest Services Team

All in all a Highly recommended stay.

Review Date: April 22, 2026

"We just got back from a wonderful week stay and couldn't have had a better time! Everything was as advertised and we had a close walk to the beach as well as dining options. The private pool was a nice escape after time at the beach. All in all a Highly recommended stay….

Reviewed By: Michael Fretschel

Loved the outdoor patios.

Review Date: February 2, 2026

"Location is perfect to walk to beaches and village. Kitchen was well stocked. Loved the outdoor patios.

Reviewed By: Kim Bennett

We'd absolutely love to stay here again!

Review Date: November 14, 2025

"We had a fantastic time here. The place was spotless and looked exactly like the photos in the listing. The hosts were incredibly attentive and helpful throughout our stay. It was an easy walk to the beach, shops, and several great restaurants — we barely needed to drive at all. We'd absolutely love to stay here again!

Reviewed By: Kenneth Mann

We'd definitely love to stay here again.

Review Date: October 6, 2025

"Lovely place! Very clean. Looked exactly like pictures on the listing. The hosts were very attentive and helpful with everything. Easy walk to the beach and to shopping and several restaurants near by. We didn't have to drive much at all. We'd definitely love to stay here again.

Reviewed By: Pat Estes

Beautiful and spacious condo

Review Date: September 22, 2025

"Beautiful and spacious condo in a great location right next to the downtown area and beach access points. The condo was beyond clean upon arrival. The kitchen was fully stocked with *clean* pots, pans, and cooking utensils. We were pleasantly surprised by the spices in the kitchen. Ample closet space with lots of extra pillows and blankets! The patio was amazing for hanging out at night. The garage had beach wagons, umbrellas, noodles, chairs, coolers, and bikes which was a big plus.

Reviewed By: Bradley Johnson

We had a great time staying here

Review Date: August 6, 2025

"We had a great time staying here with the kids, will definitely be returning.

Reviewed By: Nawaz Contractor

We are looking forward to our next stay! Highly recommend!!

Review Date: July 15, 2025

"Our stay was wonderful. We loved everything about the condo, it was perfect! Excellent location and very walkable. The Village and the beach are both just a few minutes' walk away! They supplied plenty of wagons, beach gear/toys and bikes. We are looking forward to our next stay! Highly recommend!!

Reviewed By: Teisha Gates

Excellently outfitted and decorated

Review Date: March 10, 2025

"Excellently outfitted and decorated and comfortable and minutes to beach and siesta key village. Beach the morning/early afternoon, short walk back to property for lunch, pool, and cocktails and then into the village for dinner and fun. Also easy to museums ans aquarium to mix things up.

Reviewed By: Ted Bardasz

Great place and great management company.

Review Date: December 19, 2024

"This place was exactly what my family was looking for. The home was beautiful, right across from the beach access, few minute walk to the village and the pool was heated like they stated it would be. The ceiling fan/ light didn't work on our arrival. They had a maintenance person on site within an hour and the fan/ light was fixed. Great place and great management company.

Reviewed By: Mike Pyka

Wonderful property nicely appointed and very clean.

Review Date: December 11, 2024

"Wonderful property nicely appointed and very clean. The only issue were the check in instructions. There are multiple codes for the garage, the appartment front and rear dorr and the elevator. We were given just one and had to request all other ones which is unconvenient when you cant get into the garage or cant get your luggage into the elevator.

Reviewed By: Detlev Ziesel

Thank you for such a great spot to access all the fun in Siesta Key!

Review Date: November 15, 2024

"What a beautiful place for vacation! We enjoyed the balcony in the morning and at night. We walked, shopped and ate in the village which is just around the corner. It was so convenient. The wagon, cooler, chairs, umbrellas, towels and beach toys were perfect for the white sand beaches. I will definitely return again. Thank you for such a great spot to access all the fun in Siesta Key!

Reviewed By: Kim Howell

We didn't want to leave—we were having too much fun!

Review Date: October 2, 2024

"Beautiful place! Nice comfortable furniture and bedding. Ample beach towels, beach cart and chairs. Kitchen was gloriously stocked with utensils and pots/pans/storage. Great visibility to the outdoors. Great lighting. Beautiful private pool. Lush surroundings. Very walkable area. Many restaurants, shops, beach and corner market in easy walking distance. Neat little town, folks are friendly, restaurants were nice. We happened to catch the bioluminescence at the beach for the few days we were there and then reluctantly packed up to evacuate for Helene. We didn't want to leave—we were having too much fun!

Reviewed By: Amy Rutledge

It really was perfect!

Review Date: August 16, 2024

"We will be back. Location was perfect for walking to beach and village. Pool was all to ourselves. Unit had everything you could need. Beds were comfy. It really was perfect!

Reviewed By: Donna Moran

Our condo was gorgeous and the pictures didn't even do it justice!

Review Date: July 31, 2024

"Our condo was gorgeous and the pictures didn't even do it justice! There was plenty of space and it was even closer to the beach than we thought! Shopping and dining was right around the corner! We couldn't have asked for a better location! Will absolutely visit again!

Reviewed By: Erik Anderson

The kitchen was a chefs dream!

Review Date: July 22, 2024

"The condo was spotless upon arrival. Everything was great, towels could have been better quality and bigger-they were the small hotel type. Quick walk to the beach, quick walk to the village. beach cart, chairs, noodles, coolers, umbrellas were all available for our use. The kitchen was a chefs dream!

Reviewed By: suzanne Pileggi - P-VIP

Will definitely rebook for next year!

Review Date: June 11, 2024

"The property was just as gorgeous as the pictures! Very clean and all the amenities you can think of! The staff was helpful with all questions and very responsive. Walking distance to the beach and village. The pool was loved by our 5 year old. Will definitely rebook for next year!

Reviewed By: Kayla Erickson

This property is the ideal location in Siesta Key Village.

Review Date: June 3, 2024

"This property is the ideal location in Siesta Key Village. It is a short walk to the Village and to the beach. The property was clean and well equipped whether we wanted to dine in or hit the local restaurants. I was concerned about the noise from the Village bars, but inside it was very quiet. Beach access is close and the Trolley stops nearby. It had everything we needed to head to the beach for an afternoon, or just hang out at the pool. Management was very responsive to the few questions we had. I would highly recommend this property.

Reviewed By: Kathleen Easterling

Great place

Review Date: March 20, 2024

"Great place

Reviewed By: Matthew Kolb

The beach is across the street, around the corner street with cafes, bars, shops.

Review Date: November 7, 2023

"It was amazing rest! The apartments are great and thought through every detail. The beach is across the street, around the corner street with cafes, bars, shops. We swam in the pool, used the hot tub, had a great time and had a very good time. This is the corner of paradise that we left with regret. But we will come back!

Reviewed By: Zhanna Kassymzhanova

Caribbean Dream was perfect for our long weekend in Siesta Key.

Review Date: October 13, 2023

"Caribbean Dream was perfect for our long weekend in Siesta Key. You're steps to the beach access and a short walk to the great bars and restaurants in the village. Siesta Market has everything you would need and is a short walk away as well. You can easily leave the car in the garage for your stay. Property was beautiful and communication from property manager was great. Will definitely return.

Reviewed By: Gary Prestage

Caribbean Dream

Luxury Condo on Siesta Key w/ Heated Pool, Walking Distance to Beach & Village!

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Exclusive Amenities Include: ↑↓

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