Exclusive Amenities Include: ↑↓

• 13 Minute Walk to Siesta Key Beach
• Community Tennis and Pickleball Courts
• Heated Community Pool
• Access to Community Grills
• Private Beach Access
• Close to South Siesta Key Village Dining and Shops
• Regular and Keurig Coffee Makers, Dishwasher and Kitchen Essentials Provided
• Starter Pack of Toiletry Essentials – Shampoo, Conditioner, Hand/Face Soap, Body Lotion, and Makeup Wipes
• Starter Pack of Home Essentials – Dish Soap, Sponge, Dishwasher Tablets, Laundry Pods, and Cleaning Wipes
• Beach Towels, Chairs, Cooler and Caddy Provided
• Enhanced Cleaning Protocols Provided by Our CottageClean™ Team
• Island Shuttle Transportation Available

Overview ↑↓

Bayside Endless Summer | Walk to Siesta Key Beach, Community Pool, & Tennis Court

Why You’ll Love This Home
Just a short walk to the world-renowned Siesta Key Beach, Bayside Endless Summer offers a contemporary island retreat within the amenity rich Gulf & Bay Bayside community. Start your mornings on the screened lanai, then head out for a beach walk or a relaxing dip in the community pool. Spend your afternoons exploring Siesta Key Village, or staying active on the community tennis and pickleball courts.

⭐️ Perfect For
Families, couples, and smaller groups seeking close beach access, and a comfortable home base near Siesta Key’s loved attractions.

☀️ Imagine This
Wake and get started in the open kitchen and dining space. Flip some pancakes or eggs in the well stocked kitchen. After breakfast, grab the provided beach gear and head just 0.6 miles to Siesta Key Beach, where powdery sand and clear teal waters set the tone for a perfect day.

In the afternoon, return home to relax in the comfortable living space or on the furnished lanai. If you’re feeling energized, take some laps in the community pool or play a match on the tennis courts. Later, head to South Siesta Key Village to explore shops, live music, and a variety of dining options from Captain Curt’s to Lenny’s Island Grill. As night falls, retreat to the primary suite and expansive bathroom, settle into soft linens, and end the night knowing another beach day awaits.

️ Where You’ll Sleep
• Bedroom 1: King Bed, Ensuite Bath with Walk-In Shower, TV
• Bedroom 2: Two Full Beds, Hall Bath with Walk-In Shower, TV

️ Explore The Area
• 0.6 Miles (13-Minute Walk) to Siesta Key Beach
• 1.0 Miles to Crescent Beach
• 1.3 Miles to Captain Curt's Crab & Oyster Bar
• 1.7 Miles to Siesta Key Village - Dining, Shopping, and Nightlife
• 11.5 Miles to Sarasota-Bradenton International Airport (SRQ)

Don’t Wait: This neighborhood is in an incredible location on Siesta Key and provides tranquility and privacy. Book your dream stay today. Your reservation includes peace of mind with our CottageClean™ program, featuring a six-hour deep clean and a 35-point inspection before every stay—ensuring your home feels fresh, safe, and truly vacation-ready upon arrival.

Need to Know ↑↓

This condo is located in the Gulf & Bay Bayside community. This allows guests staying at this unit to utilize the included community amenities. The community pool is seasonally heated. Starter packs of kitchen and toiletry essentials are provided for a seamless first couple of nights. Free high-speed WiFi is included.

Reviews ↑↓

Total reviews: 3

Submit a Review for Bayside Endless Summer

Review Date: June 27, 2026

"Loved the location and proximity to the beach, private beach access (was not crowded), amenities at the condo property, and attentiveness of staff. Condo was clean and exactly as described. Only one slight complaint - beds were not very comfortable - but the other pros far outweighed this one slight negative. Would definitely stay here again!

Reviewed By: Brianne

Response from The Cottages on the Key:
Hi Brianne, Thank you so much for your wonderful review! We’re delighted to hear you enjoyed the private beach access, convenient location, community amenities, and the attentiveness of our team. It’s also great to know the condo was clean and exactly as described. We appreciate your feedback regarding the beds, as guest comments help us continue improving the experience we provide. We’re so happy to hear the many positives outweighed that one concern and that you would definitely stay with us again. Thank you for choosing to stay with us. We truly appreciate your kind words and look forward to welcoming you back for another memorable beachfront getaway! Warm regards, Guest Services Team

Loved the grounds of the property and peaceful walking path with a cup of coffee in the morning.

Review Date: April 27, 2026

"We thoroughly enjoyed our stay. Condo was clean, looked just like the pictures. Comfy beds, clean furniture, plenty of beach toys, chairs, and a cooler, which made for easy trips to the beach! We appreciated the quick responses from management when we asked for more laundry detergent. Loved the grounds of the property and peaceful walking path with a cup of coffee in the morning. Our kids enjoyed spotting lizards and bunnies each day! It was great to have two pool options, at times, we had the pool to ourselves! Close proximity to the public beach (wonderful) and a short drive to restaurants, shops, and markets. We would love to stay again!

Reviewed By: Emily Wein

Great place to visit!

Review Date: April 6, 2026

"Great place to visit!

Reviewed By: Sara Vanderhoff

Bayside Endless Summer