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Cheerful Rentals

Cheerful Rentals

Member since 2024
12 rentals
107 reviews
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Anna Maria Island House
Sleeps 14, 5 bedrooms, 4 bathrooms
13 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

NEW MANAGEMENT...Welcome to Breathe Inn, your island escape where the sea breeze is plentiful and the relaxation comes naturally. This beautifully renovated 5-bedroom, 3.5-bath duplex with 2 kitchens invites you to exhale and settle into vacation mode. With two fully private units under one roof, it's...

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Featured review

"Breathe Inn"

Wonderful property and perfect for families with kids. The house was clean, well appointed with everything you could possibly need, and comfortable for everyone. The pool was always clean and well maintained....

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$761
avg per night
Bradenton Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Luxurious Waterfront Living with Resort-Style Amenities: Recently Renovated 2 Bed, 2 Bath Condo with BOAT LIFT in West Bradenton on the south side of Palma Sola Bay just UNDER 3 MILES TO ANNA MARIA ISLAND! Experience breathtaking tropical canal views from your SCREENED LANAI, and walk the sea wall to...

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$173
avg per night
Anna Maria Island Apartment
Sleeps 4, 1 bedroom, 1 bathroom
33 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This 1 BR, four-guest, condo strategically placed within short walks to the Beach (900ft, 275M), Marina (150ft, 46M), Historic Bridge Street (800ft, 245M), and Pier (1,056ft, 322M) will keep you CHEERFUL your entire stay! Coastal amenities: front screened lanai, heated pool, beach toy closet (including...

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$241
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to The Cheerful Pelican – Your Perfect Beach-to-Bay Getaway!Discover the ultimate escape in this charming 2-bedroom, 2-bathroom retreat, perfectly nestled between the stunning Gulf beaches and tranquil bay waters. The Cheerful Pelican offers the best of both worlds with sunrise views...

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Featured review

"Perfect rental"

I came down with my 87 year old mom and sister. The unit was so clean and inviting. Had everything we needed for our stay. Love the porch facing the bay, and such a quick walk to the beach. My sister...

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$300
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 3 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Kingfisher Cay is a newly renovated, beautifully designed, property boasting an outdoor covered patio, heated pool, and a games area with tiki hut, life sized connect four and corn hole. The one story bungalow has three bedrooms; one king, one queen, and one room with two twin beds. All bedrooms have...

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Featured review

"WOW! Kingfisher Rd and Cheerful Rentals what a Winning Combination!!!"

We HIGHLY recommend Cheerful Rentals Jeff and Shandra Holbrook. You will be thrilled with your choice when you choose a cheerful property. Our family trip started before we actually arrived when we first...

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$538
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

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...

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$302
avg per night
Bradenton Condo
Sleeps 6, 3 bedrooms, 3 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Waterfront Paradise Awaits at Marina Walk!Discover the ultimate coastal escape in this stunning 3-bedroom, 3-bathroom waterfront gem, nestled in the exclusive gated community of Marina Walk at Jimmy Buffet's One Particular Harbor. Perico Island's sought-after retreat is just 1.8 miles from...

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Featured review

"Fantastic vacation"

We had such a fantastic, relaxing holiday staying at Marina Walk. Jeff and Shandra are amazing, super responsive, and they made us feel welcome and at home. The views from our condo over the bay were out...

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$293
avg per night
New
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to Martinique Cheer, your cheerful beachside escape on beautiful Anna Maria Island! This rare higher-rise Holmes Beach condo offers incredible Gulf views and a prime location in a quiet, well-maintained complex. Just steps from the sand and a short stroll to the heart of Holmes Beach, you’ll...

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$241
avg per night
Bradenton Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 4 miles to Anna Maria Island

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Luxurious Bay View Living with Resort-Style Amenities: 2 Bed, 2 Bath Condo in West Bradenton and the coveted Palma Sola Bay Club on the east side of Palma Sola Bay! Experience breathtaking panoramic bay views with amazing sunsets from the privacy of your own unit and walk the grounds to live, swim, or...

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$175
avg per night
New
Longboat Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Pet friendly
  • Private pool

About this property

NEW LISTING! Welcome to Bay Dream Believer, your luxurious bayfront escape on beautiful Longboat Key! This bright and beautifully upgraded condo offers breathtaking views of Sarasota Bay through massive picture windows and an enclosed patio that lets you soak in the scenery year-round. Located just across...

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$259
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This 1 BR, four-guest condo is perfectly located within walking distance to the Beach (900ft, 275M), Marina (150ft, 46M), Historic Bridge Street (800ft, 245M), and Pier (1,056ft, 322M) to keep you CHEERFUL your entire stay!Coastal amenities: front screened lanai, heated pool, beach toy closet (including...

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$241
avg per night
Bradenton Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Luxurious Waterfront Living with Resort-Style Amenities: 2 Bed, 2 Bath Condo in West Bradenton on the south side of Palma Sola Bay just UNDER 3 MILES TO ANNA MARIA ISLAND! Experience breathtaking tropical canal views from your SCREENED LANAI, and walk the sea wall to enjoy the manatees or catch dinner!...

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$176
avg per night
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