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Dream luxury home on Anna Maria Island, heated private pool - pet friendly!

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Pool
Pool
Pool
Pool
Outdoor dining

Reviews

9.4 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 41512 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet

Spaces

Deck or patio
Kitchen
Balcony
Dining area

About this property

Dream luxury home on Anna Maria Island, heated private pool - pet friendly!

This lovely new island 2 bedrooms, 2.5 baths luxury home with private heated pool is a dream. Fishful Thinking is positioned in a superb location just steps to the white sands of the gulf-side pristine beaches, nearby trolley stop, and shops of Holmes Beach. The home offers every comfort you can imagine with an open concept living, dining, and kitchen, and tile floors throughout. The spacious 2 bedroom 2 bath home has a kitchen, living room, dining room and two bedrooms with king beds, 2 full baths and a large laundry room. The kitchen is equipped with stainless appliances, granite counter tops and all the conveniences to cook a meal in. You're welcome to make use of the large garage and amazing outdoor space with private heated pool, grill, outdoor seating. This island gem is stocked with beach towels, beach chairs, beach cart, and linens for your use during your stay. It is located just minutes from the Manatee Bridge and entrance to Anna Maria Island along with the local grocery store, pharmacy, & public beach and Skate Park. The home is literally just up the street from the public beach access. It is located to a nearby free trolley stop that runs the length of the island and is a very short distance to the local beer and wine store, as well as several bars and restaurants. Don't miss this dream home. Dogs are welcome. Pet fee is $200 per pet plus taxes, maximum of 2 pets unless otherwise approved by FDR.

Accommodates up to 4 people. Minimum Stay Required: 1 Week.
Max. parking: 2; VRC #18-000021

You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.

* Cancellation more than 90 days prior to arrival will receive a deposit refund less a $250 cancellation fee. Cancellation less than 90 days prior to arrival will forfeit all deposit received. Cancellation less than 60 days prior to arrival will forfeit all monies on account. Cancellations must be confirmed in writing.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
On-site 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 that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Holmes Beach

Located in Holmes Beach, this holiday home is near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Looking to enjoy an event or a game while in town? See what's happening at LECOM Park or IMG Bollettieri Tennis Academy. Discover the area's water adventures with snorkelling and fishing nearby, or enjoy the great outdoors with ecotours and cycling.
View more Holiday homes in Holmes BeachOpens in a new window
Map
Holmes Beach, FL

What's nearby

  • Bradenton Beach - 5 min walk - 0.4 km
  • Island Gallery West - 13 min walk - 1.1 km
  • Palmetto Avenue Beach - 17 min walk - 1.4 km
  • Holmes Beach Beaches - 19 min walk - 1.6 km
  • Manatee Public Beach - 3 min drive - 2.1 km

Getting around

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

Restaurants

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

Frequently asked questions

Is Dream luxury home on Anna Maria Island, heated private pool - pet friendly! pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Dream luxury home on Anna Maria Island, heated private pool - pet friendly!?

As of 8 Apr 2026, prices found for a 1-night stay for 2 adults at Dream luxury home on Anna Maria Island, heated private pool - pet friendly! on 24 May 2026 start from £274, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Dream luxury home on Anna Maria Island, heated private pool - pet friendly!?

On-site parking is available at the property.

What time is check-in at Dream luxury home on Anna Maria Island, heated private pool - pet friendly!?

Check-in begins at 4:00 PM.

What time is check-out at Dream luxury home on Anna Maria Island, heated private pool - pet friendly!?

Checkout is at 10:00 AM.

Where is Dream luxury home on Anna Maria Island, heated private pool - pet friendly! located?

Situated by the sea, this holiday home is within a 15-minute walk of Bradenton Beach and Island Gallery West. Palmetto Avenue Beach and Holmes Beach Beaches are also within 1 mile (2 km).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 31 out of 39 reviews
Rating 8 - Good. 4 out of 39 reviews
Rating 6 - Okay. 3 out of 39 reviews
Rating 4 - Poor. 0 out of 39 reviews
Rating 2 - Terrible. 1 out of 39 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

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
Response from VrboOwner on 6 Sept 2023
Thank you, Cindy, happy to learn you enjoyed the house and your stay. We all hope to have you back soon. Your FDR Team
Verified

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
Response from VrboOwner on 2 Apr 2025
Hi Joy, Thank you for being such a wonderful guest! We love hearing how much you enjoyed your stay in Fishful Thinking and invite you to come again. Sunny Regards, FDR Team
Verified

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
Response from VrboOwner on 6 Sept 2023
Hi Russ, Thank you for being our guest in Fishful Thinking! Florida Dreams Realty is happy to hear that you enjoyed your time in our home and on AMI. We look forward to having you again next June 2023! Sunny Regards, FDR Team
Verified

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
Response from VrboOwner on 25 Aug 2025
Hello Kris, We appreciate you staying with us at Fishful Thinking. Unfortunately, the Florida climate can take its toll on beach equipment fairly quickly. If you stay with us in the future, we kindly ask that you report any concerns with us during your stay so we can rectify them and give you a more comfortable stay. Kindly, FDR team
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

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
Response from VrboOwner on 6 Sept 2023
Hi Julie, Thank you for being a guest of Florida Dreams Realty! We are happy to hear that you enjoyed your time on the island and in Fishful Thinking. Please come back again. FDR Team
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!
Response from VrboOwner on 12 Feb 2025
HI Michelle, Thank you for being a return guest of ours! We love seeing your name come across our screen as you take such great care of the home and appreciate all Fishful has to offer! Hopefully, we will see you next year. Sunny Regards, FDR team
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!
Response from VrboOwner on 4 Jun 2025
Hello Molly, Thank you for being guests of Fishful Thinking. We would love to host you again! Sunny Regards, FDR Team
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.
Verified

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
Response from VrboOwner on 6 Sept 2023
Hi Gisele, Thank you for being our guest and for taking the time to leave a review. We are glad that you found Fishful Thinking as dreamy as we do! Please come back again! FDR Team
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

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.
Response from VrboOwner on 31 Jan 2024
Hi Michelle, Thank you for being a return guest in Fishful Thinking! We are happy to hear that you find it as charming as we do! Sunny Regards, FDR Team
Verified

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
Response from VrboOwner on 6 Sept 2023
Hi Jennifer, Thank you for being our guest in Fishful Thinking! We are glad to hear that you found it as charming as we do! Please come back again. Sunny Regards, FDR Team
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.
Response from VrboOwner on 5 Jan 2024
Jerry, Thank you for being our guest in Fishful Thinking! Very sorry we could not accommodate you for next year, this is a great vacation spot and books up fast! Please check out our website for other homes that may interest you. Sunny Regards, FDR Team
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

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
Response from VrboOwner on 6 Sept 2023
Hi Monica, Thank you for staying with us in Fishful Thinking! If you stay with us in the future, please reach out to us during your stay if something needs furnished or replaced. Our owners have a lengthy list of requirements for kitchen items, and they are more than happy to keep it supplied. Sunny Regards, FDR Team
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!
Response from VrboOwner on 10 Jul 2024
Hello Manny, Thank you for being a return guest in the lovely Fishful Thinking! You are an exemplary guest, you take such great care of the home and are a pleasure to work with! We look forward to your next stay! Sunny Regards, FDR Team
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

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
Response from VrboOwner on 21 Apr 2025
Fishful has never received a 3 star before, so we were rather taken back by this rating. We kindly ask that if there is anything that we can fix during your stay to please reach out to give us an opportunity to correct what we can to make your stay more comfortable. Concerning the comments about the railings, this home is not advertised as handy cap accessible, but we certainly will take your suggestions into consideration. Sadly, per city ordinance this home cannot lawfully have a bathroom on the ground floor because it is a never build, there is one located a half a flight up. We do apologize if there was some debris in the pool upon arrival, we try to make sure the pool is clean and clear, but it only takes one swift wind to blow leaves in from surrounding trees as this pool does not have a cage. It was serviced on the Friday during your stay as we received a report with a time stamped picture. The garage door remote was accidentally taken by the previous guest, as soon as it was returned, only a day later, we brought it to you. We understand that every rental can be improved, and we challenge ourselves to do so. Our team will take your suggestions under advisement. Sunny Regards, FDR Team
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.
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!

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