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Dream Island

Dream Island | Walk to Lido Beach, Heated Pool & Spa, Pet Friendly Coastal Home

Bedrooms: 8

Bathrooms: 8 Full

Sleeps: 14

Welcome to Dream Island! A beautifully designed estate unfolds from above, showcasing its expansive layout and resort-style pool.

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Exclusive Amenities Include: ↑↓

• Private Heated Pool & Spa with Cabana
• Located in St Armands Circle & Less than 0.3 Miles to Lido Key Beach
• 8 Bedrooms (6 Ensuite Bedrooms), 8 Full Baths
• Private Parking & Garage Space
• Putting Green & Gas Grill
• Playset, Climbing Wall & Sandbox
• Ping-Pong, Foosball Table, Arcade Games & More
• Wolf/Subzero Kitchen Appliances, Regular & Keurig Coffee Maker, Dishwasher, 2 Washers and Dryers, 2 Ovens, and Kitchen Essentials Provided
• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipes
• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipes
• Beach Towels, Chairs, Cooler, & Caddy Provided
• Dog Friendly with a Fee (Up to 25lbs)

Overview ↑↓

Dream Island | Walk to Lido Beach, Heated Pool & Spa, Pet Friendly Coastal Home

Why You'll Love This Home
Located on Lido Key, Dream Island offers a spacious coastal retreat just a short walk to both Lido Beach and St. Armands Circle. With an expansive outdoor living area and an eight-bedroom layout, this home is designed for group stays where gathering and downtime are equally easy. The outdoor space centers around a heated pool and spa with a cabana and conversation pit, two separate play areas including a rock climbing feature and a small playground, a sandbox, and a putt-putt course, plenty to keep every age group busy! A covered patio with an outdoor kitchen, dining area, and TV creates a natural extension of the home, while a separate sunken seating area offers an additional place to unwind. Inside, vaulted ceilings and an open layout provide plenty of room for group meals and shared time, with a large kitchen island and seating designed to accommodate everyone comfortably, plus an arcade game in the living room for when the energy moves indoors. The converted garage game room rounds out the entertainment options with even more ways to fill the evening hours.

‍‍ Perfect For
Large families and groups seeking a walkable Lido Key location with ample space, private bedrooms, and a strong indoor-outdoor living setup.

️ Imagine This
Start your morning with a short walk or bike ride to Lido Key Beach, where the day begins with time on the sand and in the water. Grab coffee nearby or head back home to prepare breakfast in the kitchen while the rest of the group eases into the day. In the afternoon, return to the pool area, the kids migrate between the playset and the sandbox while the adults settle into the cabana conversation pit. The outdoor kitchen makes it easy to keep meals and drinks close, whether you're spending the day poolside or squeezing in a round of putt-putt before dinner. As evening sets in, walk over to St. Armands Circle for a meal out, or stay in and let the group take over the game room, challenge each other on the arcade game, or pull out one of the many board games for a late night around the table. End the night in the spa or unwind in one of the private bedroom suites before another day on Lido Key.

Where You'll Sleep
Bedroom 1: King Bed, Ensuite Bath
Bedroom 2: King Bed, Ensuite Bath
Bedroom 3: King Bed, Ensuite Bath
Bedroom 4: Full over Queen Bunk Beds, Shared Bath
Bedroom 5: King Bed, Ensuite Bath
Bedroom 6: King Bed, Ensuite Bath
Bedroom 7: King Bed, Ensuite Bath
Bedroom 8: King Bed, Shared Bath

Explore the Area
0.2 Miles to St. Armands Circle — Dining, Shopping, and Entertainment
0.7 Miles to Lido Key Beach — Gulf Swimming and Wide Shoreline
3.5 Miles to Downtown Sarasota — Bayfront Parks, Arts, and Restaurants
7.5 Miles to Siesta Key Beach — Powdery Sand and Gulf Views

⌛ Don't Wait
Your reservation includes peace of mind with our CottageClean™ program, featuring a six-hour deep clean and a detailed 35-point inspection prior to arrival.

Need to Know
Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. We happily welcome up to 2 small dogs (up to 25 lbs) with a $250 fee per pet — breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pup's stay just as wonderful as yours. The pool is heated from November 15th to April 15th. During cooler weather, heating performance may vary depending on outdoor temperatures. This property is equipped with exterior-facing cameras, including a Ring doorbell and video monitoring of pool equipment for safety purposes.

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Reviews ↑↓

Total reviews: 8

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Review Date: July 18, 2026

"Beautiful place in a perfect location!

Reviewed By: Angela

Response from The Cottages on the Key:
Hi Angela,
Thank you for the lovely review. We're glad to hear you found Dream Island beautiful and in the perfect location for your stay. We hope to welcome you back to The Cottages on the Key soon!
Warm regards,
Guest Services Team

Was very close walk to Lido Beach.

Review Date: October 2, 2025

"This home had 8 bedrooms and 8 bathrooms and a giant pool. Was just absolutely amazing. Was very close walk to Lido Beach.

Reviewed By: Amy Eubanks

We loved our stay!

Review Date: June 9, 2025

"We loved our stay! The pool and hot tub was wonderful, and used daily; and was our saving grace on 2 rainy days!The location was perfect. We had our little oasis at the property with 5 mins walks to the beach, “beach town” shopping, and food! 10-20min drives to restaurants, city center fun, and grocery stores.We also enjoyed our walks/jogs over the bridge and back to see the sunset and beautiful ocean sceneries… we even saw a manatee on one of our walks! (Approx 4 miles round trip)We had minor issues that was resolved super quick via text!Easy check out!

Reviewed By: June Williamson

Beautiful stay!

Review Date: April 20, 2025

"Beautiful stay!

Reviewed By: Leighann Young

Great place, had a good time.

Review Date: January 21, 2025

"Great place, had a good time. The place was beautiful and had plenty of space.

Reviewed By: Matthew Miller

Fabulous house!

Review Date: January 15, 2025

"Fabulous house! Pool awesome; rooms plentiful and roomy! Property manger VERY responsive; we had a few problems with appliances and they sent someone within minutes. Only negative was not enough dresser drawer space in rooms and bathrooms need shelves or medicine cabinets

Reviewed By: Judy Kemp VIP

Thanks for making it a great trip

Review Date: October 10, 2024

"We had the pleasure of staying here a week in September for our daughter's wedding. We had a large group of family and friends - 11 of us total. The youngest was 23 and the oldest was 79. The house was perfect! Everyone had their own room, own bathroom, and plenty of seating inside and out. Nice touches that went over and above were having 2 dishwashers, 2 sets of washers/dryers, plenty of pool towels, mirrors, tvs and luggage racks in every bedroom and the outdoor kitchen. The location was perfect! Within walking distance to St Armand's with all the shopping and restaurants and also the beach. Also a short 15 minute drive to the airport for pickups and drop offs. The pool was a favorite. We were able to have all the bridesmaids meet at the house the morning of the wedding and some of the bridal party stayed the afternoon of the rehearsal poolside with us. The property management was great! Easy check in and check out instructions and a member reached out to me a couple of times just to see if we needed anything. There were even some "Congratulations" cupcakes for the newlyweds waiting for us when we arrived. What a special touch! Thanks for making it a great trip

Reviewed By: Julie Mccurry

Incredible house.

Review Date: May 13, 2024

"Incredible house. We were in town for work and had a great place to call home while we were there.

Reviewed By: Mitchell Haig

Dream Island

Dream Island | Walk to Lido Beach, Heated Pool & Spa, Pet Friendly Coastal Home

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Exclusive Amenities Include: ↑↓

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