Cheerful Rentals

01/31/2025

☀️🏝️ Coastal Cheer🏝️☀️

🔗 https://cheerfulrentalsami.holidayfuture.com/listings/267932

Stay in this charming 1BR condo (sleeps 4!) just steps from the beach (900ft/275M), marina (150ft/46M), historic Bridge Street (800ft/245M), and the pier (1,056ft/322M) 🌊🐚. You’ll be smiling your entire stay with these amazing amenities:

🏡 Coastal comforts:
✨ Front screened lanai with a lovely view (you might even spot a boat!)
🔥 Heated pool for year-round dips
🏖️ Beach toy closet—chairs, umbrellas & more!
🛋️ Pull-out sofa + air mattress for extra guests
📶 Free WiFi & 2 Roku TVs for cozy nights
🍳 Fully stocked kitchen + dishwasher
🧺 Washer & dryer for easy clean-up
🛁 Tub for the little ones!

🚶‍♀️ Walk everywhere! This quiet 16-unit condo complex is just steps from the fun of Bridge Street—restaurants, shops, and entertainment! No car? No problem! There’s a free island shuttle to explore even more 🌴.

👋 We’re local! We live just a few miles away & our real estate storefront is right on Bridge Street—stop by and say hi!

📍 Unit 14 | Second floor (so be ready for some steps!)
🚗 1 parking space included

Book your stay and get ready to relax, explore, and enjoy island life! 🌞🌊🏝️

☎️ (941) 322-4337
Cheerfulcoast.com

01/08/2025

These events make us so CHEERFUL!!! We’ll be volunteering on 2/16! See you there!

01/04/2025

It is with GREAT CHEER that we announce another addition to the Cheerful Rentals vacation home portfolio! Please meet Cheerful Oasis! This renovated 2 🛏️ 2 🛀- Bay to Beach condo is available for your weekly (or longer!) Florida Gulf (Cheerful) Coast stay!

Welcome to Cheerful Oasis – Your Bay-to-Beach Escape! Discover the ultimate island retreat at Cheerful Oasis, a delightful 2-bedroom, 2-bathroom condo perfectly situated for your next getaway. Nestled just off the walking trail to the Marina, Bridge Street, and Bradenton Beach, this serene haven o...

12/23/2024

Wishing you a week filled with joy, laughter, and holiday CHEER!!🥂🎄

🔗 https://cheerfulcoast.com/

11/15/2024

🌴We CHEERFULLY welcome you back to Anna Maria Island! Our rentals are ready to go and back in business after the 2 Hurricanes that came through.
🔗
https://cheerfulrentalsami.holidayfuture.com/
☎️(941)32-CHEER
The Cheerful Coast Group - Dalton Wade Real Estate
Shandra Mitchell Holbrook
Jeff Holbrook

09/15/2024

🌴Cheerfully gifting the AMAZING cleaners we have with a little token of our CHEERFULNESS. ☀️

09/11/2024

Cheerful FAVR conference. Always be learning! 😃

09/05/2024

It is with GREAT CHEER that we announce another addition to the Cheerful Rentals vacation home portfolio! Please meet the Cheerful Pelican! This 2 Bed/2 Bath, Beach to Bay get away is available for your short term (5 night minimum) or monthly Florida Gulf (Cheerful) Coast stay!! Enjoy Sunrise and Sunset views from two different screened lanais just steps from sand or pier. Located between Bridge Street and Coquina Beach with a trolley stop and a Gulf Drive walkway just outside your door, paradise is found! Amenities include pool, spa, tennis, pickleball, and pier!

The Cheerful Coast Group - Dalton Wade Real Estate

08/25/2024

It is with GREAT CHEER that we announce another addition to the Cheerful Rentals vacation home portfolio! Please meet Mahi Manor! This recently renovated 2 Bed 2 Bath CANAL FRONT condo with BOAT LIFT and screened LANAI is available for your monthly or mid term Florida Gulf (Cheerful) Coast stay!

07/15/2024

🌅🌅Thursday will be CHEERFUL!!!🌅🌅

We 👀 see you Cheerful Rentals! Thanks for promoting our event 🙌. Come visit the MOST Cheerful Team during next Thursday's Sundown Get Down on Bridge Street. 🌅

06/23/2024

🏝️🏡MAJOR FALL PRICE DROP FOR THIS CANAL FRONT VACATION!!!🏡🏖️

06/12/2024

It is with GREAT CHEER that we announce the newest addition to the Cheerful Rentals vacation home portfolio! Please meet Kingfisher Cay! This high-end, luxury, canal front, 3 Bed 3 Bath, completely updated paradise with private pool and gulf access is now available for your short term or mid term Florida Gulf (Cheerful) Coast stay!

06/01/2024

It is with GREAT CHEER that we announce the newest addition to the Cheerful Rentals vacation home portfolio! Please meet Intracoastal Connections! This luxury, waterfront, 3 Bed 3 Bath, completely updated paradise with INCREDIBLE views of Anna Maria Sound from your screened LANAI is available for your Marina Walk - One Particular Harbor short term or mid term Florida Gulf (Cheerful) Coast stay!

05/26/2024

It is with GREAT CHEER that we announce the next monthly vacation rental added to the Cheerful Rentals portfolio! Please meet Waterway 432! This waterfront 3 Bed 3 Bath Condo in West Bradenton on the south side of Palma Sola Bay with a Dock and Boat Slip is available for your Florida Gulf (and Cheerful) Coast retreat!

05/24/2024

It is with GREAT CHEER that we announce the next monthly vacation rental added to the Cheerful Rentals portfolio! Please meet Bay View Cheer! This bayside, 2 Bed 2 Bath, luxury retreat in West Bradenton and the coveted Palma Sola Bay Club with breathtaking panoramic bay views is available for your Florida Gulf (and Cheerful) Coast retreat!

05/24/2024

It is with GREAT CHEER that we announce the first of 3 new monthly vacation rentals added to the Cheerful Rentals portfolio! Please meet B and B's Boatshed! This waterfront, 2 Bed 2 Bath, luxury retreat with tropical views from your screened LANAI is available for your Florida Gulf (and Cheerful) Coast retreat!

04/22/2024

This makes us CHEERFUL!

03/10/2024

Bradenton Banyan Bungalow brings the CHEERFULNESS for it's first review!!! The Cheerful Coast Group - Dalton Wade Real Estate