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Island Charm, Luxury Location & Pet Friendly

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Photo gallery for Island Charm, Luxury Location & Pet Friendly

A dining area with a white table set for four, a ceiling fan, and a chandelier.
A bedroom with a bed, a window, a wall-mounted shelf with books, a wall clock, and a painting.
A spacious living area with a large island table, a ceiling fan, and a view of the outdoors.
A two-story house with a white exterior, a balcony, and a garage.
A poolside area with two chairs, a small pool, and lush tropical vegetation.

Reviews

9.4 out of 10
Exceptional

Entire home

2 bedrooms3 bathroomsSleeps 41512 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning

Explore the area

View in a map
Holmes Beach, FL
  • Place, Bradenton Beach
    ‪5 min walk‬
  • Place, Manatee Public Beach
    ‪3 min drive‬
  • Place, Holmes Beach Beaches
    ‪7 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪37 min drive‬

Room options

About the neighborhood

Holmes Beach

Located within a 5-minute walk of Bradenton Beach, this vacation home is within a mile (2 km) of Holmes Beach Beaches. The vacation home includes a private pool, a kitchen, and a balcony.
View more Vacation Homes in Holmes BeachOpens in a new window

What's nearby

  • Bradenton Beach - 5 min walk - 0.3 miles
  • Manatee Public Beach - 3 min drive - 1.3 miles
  • West Coast Surf Shop - 4 min drive - 1.8 miles
  • AMI Paddleboard Adventures - 4 min drive - 1.8 miles
  • Holmes Beach Beaches - 7 min drive - 1.5 miles

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 45 min drive

Restaurants

  • ‪The Sandbar Restaurant - ‬4 min drive
  • ‪Anna Maria Island Beach Cafe - ‬4 min drive
  • ‪The Ugly Grouper - ‬10 min walk
  • ‪Ginny's & Jane E's - ‬4 min drive
  • ‪The Waterfront Restaurant - ‬6 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Island Charm, Luxury Location & Pet Friendly

Property Highlights
• Just steps from the beautiful Gulf beaches
• Private heated pool
• 2 King Bedrooms | 2.5 Bathrooms | Sleeps 4
• Fully equipped kitchen with granite countertops
• Outdoor grill and seating area
• Large garage and parking for 2 vehicles
• Free Island Trolley stop nearby
• Walk to shops, restaurants, grocery store, and pharmacy
• Beach cart, beach chairs, beach towels, and linens provided
• Pet-friendly (up to 2 dogs)

Description
Welcome to Fishful Thinking, a beautifully appointed island retreat located just steps from the sugar-white beaches of Holmes Beach. This luxury 2-bedroom, 2.5-bath home combines coastal elegance, modern amenities, and an unbeatable location, making it the perfect destination for your Anna Maria Island getaway.

Designed with comfort in mind, the open-concept living space features stylish furnishings, tile flooring throughout, and a fully equipped kitchen with stainless steel appliances, granite countertops, and everything needed to prepare meals during your stay. Two spacious king bedrooms provide comfortable accommodations for couples, friends, or small families, while the large laundry room adds extra convenience.

Step outside and enjoy your own private heated pool, outdoor seating area, and grill — perfect for relaxing after a day spent at the beach. Beach chairs, beach towels, a beach cart, and linens are all provided, making it easy to enjoy everything the island has to offer.

Located just a short walk from public beach access, the free Island Trolley stop, restaurants, shops, grocery stores, and local attractions, Fishful Thinking allows you to leave the car behind and embrace the laid-back island lifestyle.

Accommodates up to 4 guests.
Minimum Stay Required: 1 Week
Maximum Parking: 2 Vehicles
VRC #18-000021
Dogs welcome. Pet fee is $200 per pet plus applicable taxes. Maximum of 2 pets unless otherwise approved by Florida Dreams Realty.

House Rules & Important Information
• Residential Neighborhood – You are vacationing in a residential neighborhood. Please be respectful of our neighbors by keeping noise levels at a reasonable volume at all times. Excessive noise, disruptive behavior, or any activity that disturbs neighboring properties is strictly prohibited.
• No Parties or Events – Parties, receptions, gatherings, and events are not permitted unless specifically approved in writing by Florida Dreams Realty.
• Quiet Hours – 10:00 PM to 8:00 AM.
• Occupancy – Only registered guests listed on the reservation may occupy the property unless prior written approval has been obtained.
• Minimum Age Requirement – Reservations are accepted only from guests 25 years of age or older.
• Parking – Maximum of 2 vehicles permitted on the property.
• Pet Policy – Dogs welcome. Pet fee is $200 per pet plus applicable taxes. Maximum of 2 pets unless otherwise approved by Florida Dreams Realty.
• No Smoking – Smoking or vaping is not permitted inside the home.
• Check-In – 4:00 PM
• Check-Out – 10:00 AM
•
Rental Agreement Required – A signed Florida Dreams Realty Rental Agreement is required for all reservations.
Cancellation Policy
• More than 90 days prior to arrival: Refund of deposits paid less a $250 cancellation fee.
• Less than 90 days prior to arrival: All deposits received are forfeited.
• Less than 60 days prior to arrival: All monies paid toward the reservation are forfeited.
• All cancellations must be submitted and confirmed in writing.
• Travel insurance is strongly recommended.
The vacation home is air-conditioned and features a kitchen, 2.5 bathrooms, and a balcony, and there's space to spread out with 2 bedrooms. Other standard amenities include a private pool, a washing machine, and a fenced private yard.

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  • Washer
  • Dryer
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Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Tile flooring in public areas
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • Near a hospital
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Tennis
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Horseback riding nearby
  • Snorkeling nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Unit size: 1,512 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • This property welcomes pets
  • Service animals exempt from fees

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher and a smoke detector.

Property is also known as

1757-186858
Vrbo Property

Frequently asked questions

What can I see close to this vacation home?

This vacation home is located in Holmes Beach within a short 5-minute walk of Bradenton Beach. You'll also find Bean Point Beach and Anna Maria Beach within a short drive.

Is parking available on site at Fishful Thinking – Luxury Location & Island Charm Pet Friendly Private Home?

Yes, there is a garage.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home; however, the accommodation features a private pool.

Is Fishful Thinking – Luxury Location & Island Charm Pet Friendly Private Home a good place to stay for couples?

Couples staying at this vacation home will appreciate amenities like a private pool and a kitchen as well as a heated pool.

Does Fishful Thinking – Luxury Location & Island Charm Pet Friendly Private Home have a hot tub?

No, but this vacation home does have a heated pool.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

Although pets can't stay for free, they are welcome at this vacation home.

Does Fishful Thinking – Luxury Location & Island Charm Pet Friendly Private Home have connecting rooms available?

No, there aren't connecting guestrooms at this vacation home.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Sarasota-Bradenton Intl. Airport (SRQ), which is 17.9 mi away (45 minutes by car). Another top airport is St. Petersburg, FL (SPG-Albert Whitted), which is around 18.1 mi away.

Are there rooms with balconies that I can book at Fishful Thinking – Luxury Location & Island Charm Pet Friendly Private Home?

Yes, every house at Fishful Thinking – Luxury Location & Island Charm Pet Friendly Private Home comes with a balcony.

Island Charm, Luxury Location & Pet Friendly Reviews

Reviews

9.4

Exceptional

Rating 10 - Excellent. 33 out of 42 reviews
Rating 8 - Good. 4 out of 42 reviews
Rating 6 - Okay. 4 out of 42 reviews
Rating 4 - Poor. 0 out of 42 reviews
Rating 2 - Terrible. 1 out of 42 reviews

9.6/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Cindy R.

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

Loved everything ❤️

The best overall experience!! Great restaurants near shopping , close to beach! House is amazing has everything you need great location!!
Stayed 7 nights in Jun 2023
Verified review

10/10 Excellent

Russ D.

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

Summer Vacation 2022

Fishful Thunking is a great property to stay at while on Anna Marie Island. Location is great and has all the amenities for a week stay. We will be back.
Stayed 7 nights in Jun 2022
From a partner site

10/10 Excellent

Patrick H.

Amazing place

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Excellent
Stayed 9 nights in Jul 2022
From a partner site

10/10 Excellent

Russ D.

Great second stay!

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Thank you for a great second stay! Beautiful property in an excellent location.
Verified review

10/10 Excellent

Julie S.

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

We will be back!

We will be back!
Stayed 7 nights in Jun 2021
Verified review

10/10 Excellent

Joy S.

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

Excellent two bedroom for couples

Don’t let the second story living keep you from booking this place. The huge benefit is the great socializing (open air) room under the townhouse - next to the pool. Rain or shine you can enjoy. The place is decorated beautifully. Two bedrooms of equal size and amenities makes it great for two couples to share.Great location on island.
Stayed 7 nights in Feb 2025
From a partner site

10/10 Excellent

Michelle J.

Excellent rental

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This was a very nice rental property and we had everything we needed. It is well managed, close to beaches and restaurants and very clean.
From a partner site

6/10 Okay

A guest from McFarland, WI

Good place but could be better

Rating Details: The property manager was adequately helpful. The vacation rental was clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: House of was in a location to the beach. Loved the outdoor area. Could have used more towels than what was provided. Washer machine needed a good cleaning and a lot of mildew or mold up in the vents in the bathrooms. Tv didn’t work in the outdoor pool area which was a big selling point to us for this house to watch March madness. I reached out about the tv the day of our arrival but never heard back about it during the visit. Wouldn’t be back, just expect more with the house to be in working order after paying almost 5k to stay.
Verified review

10/10 Excellent

Gisele J.

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

Perfect for Family of 4

This property was perfect for our family of 4 and spotless when we arrived! Would definitely stay here again. It had everything we needed for our 10 day stay at Anna Maria Island. Recommend the extra pool heat for this time of the year! We enjoyed fishing at the City Pier and golfing at nearby golf courses. Easy walk to the beach. Highly recommend and our mini goldendoodle loved it too!!
Stayed 10 nights in Dec 2022
From a partner site

10/10 Excellent

Michelle J.

Fishful Thinking

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This is a great vacation rental in a great location, Florida Dreams Realty is excellent to work with and they respond quickly if you need something. This is our third time renting this property, Highky recommend!
From a partner site

10/10 Excellent

Michelle J.

Fishful Thinking

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This was our second time in this rental and we loved it just as much as the first time. It is in a great location, very clean and private, and has everything you need.
Verified review

10/10 Excellent

Jennifer C.

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

Beautiful Property

This property was wonderful! The house itself was updated and gorgeous. The back yard was private, shady and perfect. There was a slight appliance issue when we first arrived, but the managing company was really responsive and got it taken care of right away for us. We couldn't have asked for anything more! I definitely recommend staying here! Great experience!
Stayed 7 nights in May 2022
From a partner site

10/10 Excellent

Molly G.

Amazing stay!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This is one of the nicest rentals we have had in our 15 years of vacationing in Holmes Beach. The house is wonderful - clean and bright. We loved lounging in the outdoor area. We had to contact the rental agency twice and each time they were responsive and addressed our issue immediately. Highly recommend!
Verified review

8/10 Good

Kris R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for a family of four. We have a 10 & 6 year old.Kitchen was well stocked with cooking pans and cutlery.Had a day and a half without electricity in the spare bedroom but the management staff was attentive.Very disappointed in the beach gear. 2 of the chairs looked like the had been plucked out of the garbage.
Stayed 8 nights in Jul 2025
From a partner site

10/10 Excellent

Rekha K.

Great Small house in Holmes Beach

Rating Details: The property manager was very unhelpful. The vacation rental was spotless. I was happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: a Modern well located rental.. close to the main road so some traffic noise. Veryyyyy clean.... And well equipped.... Perfect for a couple.... Not much sun on the pool so got to get there in the morning...
From a partner site

10/10 Excellent

Jerry M.

Great home and location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This home was perfect for our family. It was very close to the skate/dog park along with the canal for some quick fishing. Trolley NB top is 1 block away for easy access to City Pier and Pine Street shops. We really enjoyed the outdoor space with the seating area, tv, pool, and cornhole. We tried booking it again same time next year and it was already booked.
From a partner site

10/10 Excellent

Terry D.

Terrific Island Retreat

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This is a terrific home with everything we were looking for in a vacation stay: we had stayed on this same street last year and loved its central location and close walk to the beach. It’s clean, modern, spacious and we loved the large covered patio next to the pool, the perfect place to relax. I was impressed with the Florida Dreams property management team: when I was booking I had a couple of questions and they were prompt and helpful in answering them for me — almost like a friend helping me out.
Verified review

8/10 Good

Monica S.

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

Good place, good price!

The house is in a good location, two blocks from beach access. Walking distance to restaurants. The house was clean and all that was supposed to there was there. The only reason I don’t give all 5 stars was due to the kitchen being a little lacking. There were items that I looked for and couldn’t find. Nothing I couldn’t work around it was more of a nuisance. Also the beds were comfy but noisy, creaked with every move.
Stayed 7 nights in Jun 2022
From a partner site

10/10 Excellent

Manny M.

Another Great Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This is our second straight year using Florida Dreams Realty and our second year at Fishful Thinking. And we will be booking our 3rd year hear as well. Everything about this home is great. Location, layout, pool and patio all perfect. The property is well maintained and super clean. It’s ready to enjoy. Bravo again “Florida Dreams Realty” You made everything smooth and easy. You were able to help us work out a few extra things, answered all of questions and requests. You are the best!
From a partner site

10/10 Excellent

Erin G.

The perfect hideaway

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Fishful Thinking was everything we wanted and needed for our family getaway to AMI! The house is beautiful, bedrooms and bathrooms are great. The outdoor space, though, was unbelievable! We spent so much time downstairs in the outdoor living room, even when the weather was yucky. Only a few small needs in the house: more towel hooks and bars! There was nowhere to hang items. And the washer/dryer need to be cleaned out. The washer's door lining was very moldy. Small maintenance needs, though. Everything else was perfect!
Verified review

6/10 Okay

Peggy W.

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

Very cute house great location, but nothing’s perfect

The house is very well decorated, and a fun floor plan! You have to walk upstairs to the pool bathroom, which was OK for us but not great for the seniors who were with us. The pool is very small, but we had a good time in it. However, there is no railing to get in and out, which is hard for little kids and seniors. Something you’d never think of would be a problem, but the little tiny pebbles all around the pool are a real pain and hurt your feet. They get all over the patio and we had to wear flip-flops all the time and sweep off the patio because the little pebbles were everywhere. Like walking on Legos! Ha ha! No bars in the showers to hold onto which poses a big safety hazard. Kitchen was well stocked with pots and pans, and everything you need, and the place was clean. There was not enough towels and there had been debris in the pool when we arrived and nobody came the 10 days we were there to clean the pool. I bought a net from the dollar store and swept the pool myself. There was no garage door opener when we got there which is one of the things they will charge you for if you lose it. So make sure that the garage door opener is there when you arrive. We had a blast as a family, but we will not return to this specific house. Neighborhood is amazing and close to the beach. We rented a golf cart and it was great to get around town. Traffic does get really bad on Ana Maria.
Stayed 9 nights in Mar 2025
From a partner site

10/10 Excellent

Patrick H.

Fishful thinking is always perfect.

Rating Details: The property manager was very helpful. The vacation rental was clean. I was happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Overall always a great experience. The only issue is several outlets do not work and need replacing.
From a partner site

8/10 Good

ROGER G.

AMI SEPT 22

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: GOOD QUALITY HOUSE, GOOD LOCATIONNEEDS FANS IN OUTSIDE LOUNGE/ DINNING AREA ALSO WOULD HAVE LIKED A KETTLE TO MAKE TEA
From a partner site

6/10 Okay

Linda T.

Fishful Thinking

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: House was very nice. Pool was too small. Proximity to Beach a little farther than we like. A couple of maintenance items - key hard to work in lock (should replace knob) and guest bath shower doors need adjustment as they knock. I would recommend with the reservations of pool and proximity to beach.
From a partner site

10/10 Excellent

Kim K.

A+

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Property has many great attributes! This includes the location being a short walk to the beach and a quick golf cart ride to shops and restaurants. The home was extremely clean and perfect size for a family of 4. We utilized the covered patio most of the time and kids loved the pool. We quickly went from beach to pool each day. The management company was extremely helpful and quick to respond to the couple of questions we had. Great place!