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1141 sq. ft. 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 offers the ideal balance of relaxation and convenience. With trolley stops and the Gulf Drive walkway right outside your door, every adventure begins just steps away.
Relax and unwind on the lanai, where breathtaking water views set the tone for your stay. This quaint condo complex provides a peaceful atmosphere while keeping you close to Bridge Street’s vibrant dining, shopping, and entertainment options. With one reserved parking space and access to the island’s free shuttle, exploring Anna Maria Island is a breeze.
Your second-floor condo (elevator temporarily unavailable) ensures a private and tranquil experience. Guests will enjoy access to the pool and provided beach essentials, including chairs and an umbrella, making every trip to the sand stress-free.
Your local hosts live just three miles away and are always available to assist with any needs or provide insider tips to enhance your stay. Visit our real estate storefront at 119 Bridge Street, just steps from the condo, to say hello or learn more about the area.
Cheerful Oasis is your perfect home base for enjoying the best of Anna Maria Island. Book now and experience the charm of this Bay-to-Beach retreat!
24-hour checkin
Fire Extinguisher
Essentials
Shampoo
Suitable for infants
Shower
Hot water
Extra pillows and blankets
Cooking basics
Beach essentials
Bay
Marina
Toilet
Car not necessary
Dining area
Bird watching
Boating
Eco tourism
Paddle boating
Shopping
Water sports
Wildlife viewing
Beach
Near ocean
Boat
Veranda
Long term stays allowed
Cycling
Deepsea fishing
Fishing
Fishing bay
Fishing fly
Fishing surf
Golf
Hiking
Jet skiing
Parasailing
Pier fishing
Scuba or snorkeling
Water Skiing
Snorkeling
Snorkeling diving
Surfing
Swimming
Wind surfing
Dining table
Outdoor furniture
Outdoor sunloungers
Clothing storage
Baking sheet
Coffee
Wine glasses
No Booking or Service Fees
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Dec 04 - Dec 05 2025 | $138 | 5 nights | |||
Dec 05 - Dec 06 2025 | $151 | 5 nights | |||
Dec 06 - Dec 07 2025 | $154 | 5 nights | |||
Dec 07 - Dec 08 2025 | $134 | 5 nights | |||
Dec 08 - Dec 11 2025 | $125 | 5 nights |
Fees:
Notes:
House Rules
Check-in: 4 pm
Check-out: 10 am
Cancellation Policy
100% refund up to 14 days before arrival
50% refund up to 7 days before arrival
Last updated on December 04, 2025
Matthew B.Everything in the condo was very updated and had a great look and feel. The beds were comfortable, and the kitchen was well-stocked with all that was needed to cook in the unit. The balcony was spacious with comfortable chairs to relax on. Also. the view of the bay was very nice from the balcony, the living room and master bedroom. We also liked the short walk (10 minutes) that the condo is to historic Bridge Street. The owners have done a great job with this unit thinking of all the details for a great stay! Our family really enjoyed this unit and AMI!
Stayed: October 2025 Submitted: November 03, 2025
GailThis beautifully decorated, stylish, and immaculate condo is a short walk to the beach, restaurants, and shops.The well-appointed modern kitchen is equipped with everything you could possibly need. The lanai, with its lovely bay view, is the perfect spot to enjoy your morning coffee or an evening libation. The Master BR has the most gorgeous en-suite, with an amazing walk-in shower stall. The condo offers every amenity you can think including oversized bath and beach towels, soft bedding and blackout shades.As if this wonderful Oasis was not special enough, after check out and arriving at the airport, I received a call from the host informing me that they had found my wallet with my ID, cash and credit cards, that I had left behind, and he immediately brought it to me at the airport to avoid delaying my return trip back home!I cannot emphasize enough how much we enjoyed our stay and my gratitude to the hosts their hospitality, responsiveness and thoughtfulness.
Stayed: September 2025 Submitted: October 16, 2025
AaronWe had a fantastic stay at this property. The place was spacious, spotless, and exactly as advertised. The beach chairs, an umbrella, and other accessories made our beach days super convenient. The beach was just a short walk away, and the pool was close by as well. The location was perfect and within walking distance of restaurants and everything we needed. The hosts were responsive throughout our stay. We would stay here again and recommend it to anyone looking for a relaxing beach getaway!
Stayed: June 2025 Submitted: June 29, 2025
LynneYou can't beat the location of this lovely 2 bedroom condo. Across the street from the beach and an easy walk to many restaurants and shops, we were impressed by how quiet this unit was. A lovely deck overlooks the Bay - a perfect spot for a glass of wine or morning coffee. There is every amenity you could ask for on your vacation! The kitchen has a wide selection of dishes, pots/pans, glasses, cutlery & utensils. Appliances include coffee maker, toaster, air fryer, microwave, convection oven, fridge/freezer and dishwasher. A large size washer and dryer in your unit is so convenient. Soaps for kitchen and laundry were provided! There are lots of big, fluffy towels, 2 full baths (1 walk-in shower, 1 tub) and comfy beds for your stay (2 singles and a king). Lawn chairs and coolers for your days on the beach and TVs in the living room and bedrooms (with streaming and cable!) for rainy days...or use the umbrellas to get to your car or the bus to go in town! It's all here. An absolute gem of a property.
Stayed: February 2025 Submitted: March 03, 2025
PamDespite an unseasonably cold and somewhat rainy week, we could not have been happier with our stay on Gulf Drive in Bradenton Beach. It started with the personal service and help we received from Jeff at the time we booked. On the day we arrived he personally met us at the condo to allow us to enter a few hours early. The condo itself is in an excellent location within walking distance of multiple restaurants and right across from the beach. We definitely plan to return and will be renting through Cheerful Rentals.
Stayed: January 2025 Submitted: January 29, 2025
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