Condo

A Private, Spacious and Updated Home Away From Home. Heated Pool. Paddleboards & Beach Gear!

Photo gallery for A Private, Spacious and Updated Home Away From Home. Heated Pool. Paddleboards & Beach Gear!

Spacious living room and dining area
Fully equipped kitchen for just about any type of meal preparation. All Stainless Appliances, including a dishwasher!
Dining for six
Private balcony area with outdoor seating overlooking the courtyard
Primary bedroom with two queen size beds

Reviews

9.4 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 6

Popular amenities

  • Heated pool
  • Onsite parking available
  • Kitchen
  • Air-conditioning
  • Barbecue
  • Balcony

Rooms & beds

2 bedrooms (sleeps 6)

bedroom

2 Queen Beds

bedroom

1 Queen Bed and 1 Single Bed

1 bathroom

Hall

Bathtub or shower

Spaces

Deck or patio
Kitchen
Balcony

About this property

A Private, Spacious and Updated Home Away From Home. Heated Pool. Paddleboards & Beach Gear!

Island Paradise Cottages, centrally located in Madeira Beach inside a quiet and secure neighborhood, and just off the main road. The cottages are just a 5 minute walk over to the very best beaches that the Gulf of Mexico has to offer, and you are in very easy walking distance of Johns Pass Village, with many excellent restaurants, activities, and attractions. Access to the bay for paddle boarding and kayaking is just a short walk away through the neighborhood, and you can catch the beach trolley nearby if you need to get a little further away.



Our little piece of paradise is perfectly setup for vacationing and relaxing with lush landscaping, an island style tiki hut for socializing and BBQ grilling, a beautiful heated pool, as well as a full inventory of bikes, kayaks, paddle-boards and games exclusively for our Guests' use.



This cottage, affectionately known as "Villa Paradiso" offers:



-- Private balcony area with outdoor seating overlooking the courtyard



-- Primary bedroom with two queen size beds



-- Second bedroom with queen bed and twin bed



-- Central bathroom with tub/shower combo



-- Cozy living room and dining areas.



-- Fully equipped kitchen for just about any type of meal preparation. All Stainless Appliances, including a dishwasher!



-- Direct Access out to the Tiki Picnic Area.



-- High-speed WI-FI, Smart TV, & Assigned Parking



-- Year round heated pool with beautiful patio area



-- Thatched Tiki Style picnic area with propane BBQ Grills and plenty of seating



-- On-site coin operated Washers and Dryers for laundry



-- Free use of kayaks and beach gear



-- All linens and towels (both Beach and Bath) are provided. 24 hour guest services hotline for any issues or questions.

-- Gas Firepit in the Courtyard for Evening Relaxation.



We help make the most of your vacation by providing Free Admission to some of the area's top activities & attractions each and every day, including Busch Gardens, The Clearwater Aquarium, The Dali Museum, The Tampa Zoo, evening cruises, bike rentals and more! Create exciting memories, have more fun, and truly experience your destination. (One Free Ticket Per Day, Per Activity. Free Fun Program not eligible for stays over 28 days)

A Professionally Managed Vacation Rental Property Following CDC Recommended Guidelines, and Providing 24hr Guest Support.



All our properties include free parking, a complete linen set, beach and bath towels, a starter set of paper goods, hand soap, dishwashing soap and trash bags, free WiFi access, and a 24hr Guest hotline for any issues. Need a Pack n' Play for your stay? We've got you covered - no charge!

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About the area

Madeira Beach

Located in Madeira Beach, this condo is near theme parks and near the beach. Shoppers can check out John's Pass Village & Boardwalk, while everyone can enjoy the natural beauty of St. Petersburg - Clearwater Beaches and Pass-a-Grille Beach. Looking to enjoy an event or a game while in town? See what's happening at Tropicana Field or St. Pete's Historic Coliseum. Looking to get your feet wet? Jet skiing, parasailing and fishing adventures can be found near the property.
Map
Madeira Beach, FL

What's nearby

  • St. Petersburg - Clearwater Beaches - 6 min walk - 0.5 km
  • Madeira Beach - 6 min walk - 0.5 km
  • John's Pass Village & Boardwalk - 9 min walk - 0.8 km
  • Hubbards Marina - 12 min walk - 1.1 km
  • St. Petersburg Municipal Beach at Treasure Island - 19 min walk - 1.6 km

Getting around

  • St. Petersburg, FL (SPG-Albert Whitted) - 24 min drive

Restaurants

  • ‪Delosa's Pizza - ‬11 min walk
  • ‪Hooters - ‬13 min walk
  • ‪Bamboo Beach Bar & Grill - ‬9 min walk
  • ‪Sculley's Restaurant - ‬12 min walk
  • ‪Caddy's Madeira Beach - ‬14 min walk

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 26 out of 33 reviews
Rating 8 - Good. 5 out of 33 reviews
Rating 6 - Okay. 1 out of 33 reviews
Rating 4 - Poor. 0 out of 33 reviews
Rating 2 - Terrible. 1 out of 33 reviews

9.2/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

Laura W.

Wonderful Cottage

We very much enjoyed our stay at Villa Paradiso. The check-in process was easy and smooth. The cottage was clean and stocked with anything we might need. Being across the street from the beach access was handy so we didn't have to fight to find and pay for beach parking. We walked to John's Pass Village multiple times for shopping and dining. We would definitely stay again!
Response from VrboOwner on 6 Apr 2026
Thank you for your wonderful review, Laura. We’re thrilled to hear you enjoyed your stay and found the check-in process to be easy and smooth. It’s fantastic to know that the cleanliness and amenities met your expectations. We’re glad you appreciated our convenient location, just across the street from the beach access, and the proximity to John's Pass Village for shopping and dining. We look forward to welcoming you back for another great stay!
From a partner site

10/10 Excellent

Steven B.

Wonderful beach cottage!

This is our first time staying and the cottage is perfect, and so close to the beach. There are kayaks, SUP boards, and a fire pit. Management is responsive and friendly if you have any questions. We hope to be back again soon!
Response from VrboOwner on 16 Jan 2026
Thank you for your wonderful feedback, Steve! We're thrilled to hear that your first stay was perfect and that you enjoyed the proximity to the beach. It's fantastic that the kayaks, SUP boards, and fire pit added to your experience. Our team is always here to assist with any questions. We hope to welcome you back for another amazing visit soon!
Verified

8/10 Good

Marcia N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved this little cottage and how close it was to the beach and Johns Pass shopping. The interior was clean, pretty and comfortable. Our only complaint inside was that the beds are very hard. The grounds could use some work and the firepit wouldn't light. Bummer. My only other suggestion (and complained about by other guests) is that the pool maintenance come three times a week and in between a lot of debris and insects collect the pool, so it would be perfect if there were a skimmer onsite to clean it up before use. The management is very prompt at answering questions as well. Overall, a very nice place to stay and I would recommend it to others.
Stayed 4 nights in Apr 2026
Response from VrboOwner on 15 Apr 2026
Thank you for your feedback, Marcia. We’re glad you loved the cottage and its proximity to the beach and Johns Pass shopping. It’s great to hear you found the interior clean and comfortable. We appreciate your insights about the beds and have taken note to make improvements. We’re also addressing the grounds and firepit issues to ensure a better experience. Regarding the pool maintenance, we appreciate your suggestion and will look into providing a skimmer for guest use. It’s wonderful to know our management team was helpful during your stay. We hope to welcome you back for another enjoyable visit!
From a partner site

10/10 Excellent

Demi

Beautiful Cottages

Great location and beautiful cottages
From a partner site

8/10 Good

Jessi L.

Spring break family of 5

There was a lot of great things about this stay, a few inconveniences. So the positives.. the location was great. Not far from the beach, a quick walk to John’s pass to help avoid parking fees. The house was cute and clean. I was worried about it being spring break and our area feeling packed, but it wasn’t. The pool is super small, but my boys still enjoyed it. The only inconveniences I have was the laundry. We typically keep our stuff washed to have to avoid going home with a dirty laundry and keep our beach towels clean. There is a laundry area, it was just a pain to have to have to pay for it and need to have quarters. Also there were no laundry baskets in the house so trying to find ways to carry the laundry across the way was inconvenient. Other than that everything else was great!
Response from VrboOwner on 15 Apr 2026
Thank you for your feedback, Jessi. We're glad to hear you enjoyed the great location and found the house cute and clean. It's fantastic that your boys had fun at the pool and that the area wasn't crowded during spring break. We appreciate your feedback regarding the laundry facilities. We'll explore more convenient solutions, including the possibility of providing laundry baskets for easier transportation. We hope the positives outweighed the inconveniences and look forward to welcoming you back for another great stay!
Verified

10/10 Excellent

Matthew N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location location location

Extremely close to the beach. Nice amenities and overall great location.
Stayed 6 nights in May 2023
Verified

10/10 Excellent

Wendy P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and nice property

My husband, daughter, and grandson stayed in Villa Paridiso for a long weekend during March. We found the location so handy to John’s Pass and the h by villa was so quaint. We would definitely stay here again!
Stayed 5 nights in Mar 2022
Response from VrboOwner on 13 May 2022
We are very happy you enjoyed your stay. Thank you for the wonderful review. We look forward to hosting you again!
Verified

10/10 Excellent

shayne q.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Everything we expected

Great location and very clean. Host was responsive to all requests.
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Jimmy P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great beach spot

Great location, plenty beds and spacious bedrooms, cold AC. Would recommend. Only thing is the power went out in a couple rooms and we had to reset the breaker, and more bathroom supplies (hand soap, body wash, shampoo) would have been nice
Stayed 3 nights in Jun 2024
From a partner site

10/10 Excellent

Sean J.

Wonderful beach vacation

Island Paradise was awesome! We stayed in a 2 bedroom cottage and I was very clean, spacious and fun! Very close to the beach and Johns pass, my kids like to fish and there is a spot across the street to canal fish. We had a lot of fun the pool as a swim jet which was hours of fun for the kids.
From a partner site

10/10 Excellent

Meg V.

Great location in a lovely Florida town

This was a perfect location in a lovely Florida town. We loved the fire pit and pool area at our cottage. We made some great new friends sitting around the community area of this resort. We also loved that the beach plus John’s pass was in walking distance. The cottage had all the necessary amenities of home. We thoroughly enjoyed our time at island paradise!!
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

Julie

Liked: Cleanliness, amenities, property conditions & facilities, communication
The property was recently updated, was clean and decorated in a beachy and modern feel. The neighborhood was quiet and the outdoor pool and space was enjoyable. We wished we had more time to hang out by the firepit at night. The kitchen had the basics and the beds were comfortable. We will definitely come here again.
Stayed 3 nights in May 2024
Verified

10/10 Excellent

Sally S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place with lots of space.

The property was exactly as described. Clean, updated and spacious. Good for several couples, or a larger family with kids. The pool was nice and clean. Our neighbors in the other cottages were friendly! Would stay again!
Stayed 4 nights in Jul 2022
Response from VrboOwner on 24 Aug 2022
Thank you!
Verified

10/10 Excellent

Brandi F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful

I was so pleased with our stay! The villa’s decor was beautiful! Everything we needed was at our fingertips. We had access to bikes, beach chairs, paddle boards, and much more! I could not have been happier! Wonderful place!
Stayed 4 nights in Jul 2020
Verified

10/10 Excellent

Christina H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Property

The property grounds were just as pictured. The atmosphere was calm and inviting and house #3 was cozy and spotless. I absolutely loved having the garage full of 'toys' to play with. We took the kayaks out and rode bikes around the neighborhood. I will be booking a stay here again in the near future.
Stayed 3 nights in Feb 2024
From a partner site

10/10 Excellent

Danielle P.

Beachy vibes!

Loved it! Super beach my feel! Close to John’s pass! Lots of eating out options. 3 min walk to the beach! And a pool perfect size got little kids! Tv in every room! Community area for eating outside and 2 grills! Loved our cottage so much! It was clean!
From a partner site

10/10 Excellent

Michelle

Beach stay

We really enjoyed our stay in the Villa Paradiso.. It was a cute little place tucked right off the street. Only about 5 min walk to beach. Close to walk to restaurants, ice cream, and many shops. We did have an issue when we arrived with the code not working, but the batteries was dead in lock. However they was very quick to come out and change it and get us in our place.
From a partner site

2/10 Terrible

Kathleen N.

Not as described...

Unfortunately the Island Paradise Cottages are not as described or pictured. So unfortunate as the property could be great with better management. Upon arrival the unit/Villa Paradiso was missing furniture, mismatched stained bedding, chipping paint, filthy everywhere and the porch looked like a crime scene. The pool was not heated and described in listing and was freezing. The pool area was a dirty disaster. A caretaker popped in for a second and peeked around-never lifted a finger to clean a thing. Was literally onsite for less than 5 minutes. The property had not been cleaned in a decade. The property could be so cute and it's proximity to beach and town is nice, but the other guests also complained of the mess and dirt other than the guy smoking weed at the pool, he thought it was fine.
Verified

10/10 Excellent

Caroline L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Toller Urlaub

Top Lage, nette Unterkunft
Stayed 7 nights in Dec 2022
From a partner site

10/10 Excellent

anna j.

Villa paradiso

Excellent stay at villa paradiso. Location was perfect with bars and restaurants on your doorstep and the beach just down the road. Villa was very spacious and well maintained and came with so many extras. I would highly recommend this rental.
Verified

10/10 Excellent

Melissa L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

We rented 3-Villa Paradiso as a family of 6. The location was great, it is within walking distance to restaurants & shopping and a 5 min walk to the beach. We loved the outdoor fire pit, grill and Tiki-hut for dining and relaxing in the evenings. The beds were comfortable, the kitchen was stocked with everything we needed and having a laundry room available was nice to wash towels mid- week. The pool is small but clean. The garage stocked with beach chairs, coolers, paddle boards & bikes was one of our favorite things about Island Paradise. Overall great place to stay, we would rent again.
Stayed 5 nights in Oct 2022
Verified

10/10 Excellent

Jennifer

Liked: Cleanliness, amenities, property conditions & facilities, communication
This was a great property for our family. Lots of room, beautifully updated and lots of beach accessories for us to use.
Stayed 4 nights in Apr 2022
Verified

6/10 Okay

Tonya R.

Liked: Check-in, location, listing accuracy
Disliked: Cleanliness, communication

Just like the pictures

Cute place. Nice location within walking distance to everything. Only thing was I was not clean at all. I had to call because the floors were filthy not mopped or swept . Wrappers under the beds the walls had coffee stains on them . The cleaners didn't do a good job at all. Get new good cleaners and I would come back. Otherwise nice and roomy and comfortable. Liked that it had Roku. The pool is very small too. But it was a fun vacation.
Stayed 7 nights in Apr 2022
Response from VrboOwner on 21 May 2022
We take cleaning very seriously. Sorry for any inconvienence. Thank you for your honest feedback. This information is very helpful. We will work to take care of those items right away. We always have guest services available and the cleaners are happy to return.
Verified

8/10 Good

Beth Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great

One thing would help if they did provide small bottles of shampoo, conditioner and bath gel would be a great plus. Otherwise, I would definitely recommend this place. Great location! I like to travel light so having to bring extra stuff can be a nuisance and a lot of stores don't always carry small bottles of stuff.
Stayed 2 nights in Feb 2022
Verified

10/10 Excellent

Sharon M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very relaxing

My Sister and I enjoyed the trip and the stay in the darling cottage was perfect!
Stayed 4 nights in Jan 2022
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