Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream
Caribbean Dream by Anna Maria Vacations Home in Holmes Beach, Florida VRC17-000129
Experience the ultimate Gulf Coast escape at Caribbean Dream, a luxurious three-level retreat designed for families and friends seeking relaxation and adventure. Located less than five minutes from the white sandy beaches of Holmes Beach, this spacious five-bedroom, four and a half bath home offers stunning panoramic views from its rooftop deck, private pool, and relaxing in-ground spa. Perfectly positioned near shopping and dining, Caribbean Dream invites you to create unforgettable memories on Anna Maria Island.
Highlights • 3-minute walk to Holmes Beach • 5 Bedroom / 4.5 Bathroom • 4 Kings, 1 Queen, 1 Twin sleeper sofa • Rooftop deck with beach views • Private pool with in-ground spa • Outdoor bar and grill • Multiple balconies and expansive outdoor decks • Pool table • Short drive to local shops, dining, and attractions • Elevator access to all levels • 5 Parking spaces
Enjoy your vacation with a luxurious private pool, relaxing in-ground spa, and a rooftop deck featuring bar-height tables and Adirondack chairs offering breathtaking views. The outdoor space boasts a covered deck with a bar, seating area, and grill for easy outdoor entertainment. Inside, the home features a game room with a pool table, a den with a TV and wine fridge, and a modern kitchen perfect for preparing large meals or casual snacks.
The heart of this home is the third-floor open-concept kitchen, dining, and living area, seamlessly connected for entertainment. The kitchen shines with sweeping granite countertops, a generous island, and stainless-steel appliances. The living room is furnished with two couches, an armchair, and a flat-screen TV, with wall-to-wall sliding doors leading to the large deck and rooftop area, perfect for outdoor dining or just relaxing in the fresh ocean air.
The three grand bedrooms each feature luxurious king beds, balconies, and ensuite bathrooms with double vanities and walk-in showers, offering privacy and comfort. The remaining two guest rooms, one with a queen bed and one with a king, share a jack-and-jill bathroom with a shower-tub combo. All bedrooms are equipped with plush bedding, TVs, and ample closet space for a restful night’s sleep. A twin pull-out couch in the living area provides additional sleeping options. The home also offers a washer and dryer for added convenience.
Room Details • Primary Bedrooms: King bed, ensuite with double vanity and walk-in shower • Second Bedroom: King bed, ensuite with double vanity and walk-in shower • Third Bedroom: King bed, ensuite with double vanity and walk-in shower • Fourth Bedroom: King bed, jack-and-jill bathroom with shower and tub • Fifth Bedroom: Queen bed, jack-and-jill bathroom with shower and tub • Living Area: Twin sleeper sofa
Caribbean Dream offers elevator access to all levels, a fully equipped outdoor kitchen with a grill, and a large, heated pool and spa with in-water seating. The prime location close to Holmes Beach beaches, shops, and dining makes exploring Anna Maria Island effortless and fun.
Reserve your stay at Caribbean Dream today and enjoy the perfect blend of luxury, relaxation, and island adventure. Whether lounging poolside, soaking in the spa, or relaxing on the rooftop deck with panoramic views, this home is your gateway to a memorable Gulf Coast vacation. Book now and start creating lifelong memories with your loved ones!
- This property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.
This property does not allow pets.
5 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.
This home is managed by Anna Maria Vacations, an Anna Maria Island property management company.
We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.
Please see our Anna Maria Vacations Rental Policies for full details.
Please Remember: "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." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Our prices include all fees. No hidden fees.
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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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and ecotours.
Anna Maria Island Museum and Historical Park - 3 min drive - 2.1 km
Anna Maria City Pier - 3 min drive - 2.1 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 42 min drive
Restaurants
Anna Maria Island Beach Cafe - 6 min drive
The Ugly Grouper - 3 min drive
The Sandbar Restaurant - 17 min walk
The Waterfront Restaurant - 4 min drive
Ginny's & Jane E's - 14 min walk
Frequently asked questions
Does Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream?
As of 11 Apr 2026, prices found for a 1-night stay for 2 adults at Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream on 23 May 2026 start from £595, 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.
Is Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream pet-friendly?
No, pets are not allowed at this property.
How much is parking at Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream?
On-site parking is available at the property.
What time is check-in at Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream?
Check-in begins at 4:00 PM.
What time is check-out at Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream?
Checkout is at 10:00 AM.
Where is Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream located?
Situated by the sea, this holiday home is within a 10-minute walk of Bradenton Beach and Palmetto Avenue Beach. Island Players and Anna Maria Island Museum and Historical Park are also within 1 mile (2 km).
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Hi, Kelly, thank you for staying with Anna Maria Vacations! We’re so happy to hear you had a fantastic time at Caribbean Dream. We hope to welcome you back for another island escape soon!!
Kitchen was well stocked and we were given starter packs for dishwasher and laundry which were a nice addition. Rooms were clean and and adequately equipped. Pool area was relaxing. The patio could use a mini fridge and garbage container.
Christine H.
Stayed 7 nights in Oct 2025
Response from VrboOwner on 5 Nov 2025
Thank you for sharing your experience! We’re so glad to hear you enjoyed the well-stocked kitchen, the starter packs, and that the rooms and pool area met your expectations. Your suggestions for a mini fridge and garbage container on the patio are excellent—we truly appreciate the feedback and will consider these improvements to make future stays even better. We’d love to welcome you back anytime!
We had a great time with our family for spring break
Brent G.
Stayed 7 nights in Mar 2025
Response from VrboOwner on 14 Apr 2025
Thank you for choosing us for your recent stay!
Every review and every star you give us makes a huge difference to our success. If you enjoyed your stay, we'd love your 5-star review!
We hope to host you again in the future!
This was a great house for a family gathering. Great location for beach access, restaurants and shopping. The elevator was so helpful for hauling our stuff up/down to the 3rd floor. The pool was fun! I'd stay here again and would recommend this home.
Karen K.
Stayed 7 nights in Aug 2024
Response from VrboOwner on 12 Dec 2024
Thank you for your thoughtful review! We're so glad the house was perfect for your family gathering and that the location made it easy to access the beach, restaurants, and shopping. It’s great to hear the elevator was helpful, and that the pool added to your enjoyment. We’d love to welcome you back for another fantastic stay and appreciate your recommendation!
Loved everything about the house! Location, decor, pool, hot tub, elevator, layout...couldn't ask for a better vacation rental! Rental company was also on top of making sure we were well taken care of!
Kayce B.
Stayed 7 nights in Aug 2024
Response from VrboOwner on 11 Dec 2024
Thank you so much for your amazing review! We’re thrilled to hear that you loved everything about the house, from the location and decor to the pool, hot tub, and elevator. It’s great to know that the layout worked so well for you and that our team helped make your stay even more enjoyable. We truly appreciate your kind words and would love to welcome you back for another unforgettable vacation!
Beautiful home. Very clean and easy to communicate with owners. Only complaints is the main beds are very hard. The front door pad didn’t work and some other small issues were quickly fixed. Great location to the beach and to the town. Would definitely stay again.
Unit was clean and well cared for. Owners have thought of everything including a wagon to transport essentials to the beach. Easy access to sunrise and sunsets. Communication with property manager was excellent!
Debra K.
Stayed 7 nights in Dec 2024
Response from VrboOwner on 16 Jan 2025
Thank you for your wonderful review! We’re so happy to hear that you found the unit clean and well cared for, and that the wagon for beach essentials was a helpful touch. It’s great to know that the location made it easy for you to enjoy both the sunrise and sunset, and we’re glad you had excellent communication with our property manager. We hope to welcome you back for another seamless and enjoyable stay!
Beautiful home, great location. Only complaint, wish owners would furnish a pack and play and high chair. Hard to travel with those items.
Cindy G.
Stayed 7 nights in Feb 2020
Response from VrboOwner on 23 Mar 2020
Thank you for the review, Cindy! We are so happy to hear that you enjoyed this beautiful home and the great location! Due to liability concerns, owners are not required items such as baby items. We do offer a concierge service to our guests and would have been more than happy to get these rented and delivered to Caribbean Dream for your stay. Thank you again and we hope to welcome you back to Anna Maria Island in the future!
We had a great vacation in this lovely home! 6 adults and 4 kids, plenty of room , 2 minute walk to the beach, kids loved swimming in the pool and the hot tub! Had an issue with the barbecue but was fixed immediately.... only complaint I would have is that they could use a new and bigger barbecue....I would definitely rent this house again!
Monique F.
Stayed 7 nights in Feb 2020
Response from VrboOwner on 23 Mar 2020
Thank you for the 5 star review, Monique! We are so happy to hear that you and your family had a great vacation at Caribbean Dream! We are glad that our Team at Anna Maria Vacations was able to fix the grill for you in a timely manner! We appreciate the feedback and will pass this along to the owner of the home for further review! Thank you again and we look forward to welcoming you back to the Island in the future!
We had an amazing visit. Love the floorplan, kids playing and laughing throughout. Bathrooms are a dream and very spacious. I want to build this property back home in the midwest! Each floor has room to play and visit or take day naps. A short walk to the beach, and close enough to walk back for lunch. The pool was so fun and the hot tub made every evening a perfect setting for relaxing and enjoying every moment. A wonderful setting to reflect and recharge. We definitely will be recommending this property to any and everyone. This place is truly a jem!
Amber P.
Stayed 7 nights in Mar 2025
Response from VrboOwner on 9 Apr 2025
Thank you so much for the wonderful review! We're thrilled to hear that you and your family had an amazing time at our property. It's truly gratifying to know that you loved the floorplan, the spacious bathrooms, and the convenient location close to the beach. We're glad the pool and hot tub were a hit, providing the perfect setting for relaxation and recharging. We appreciate your enthusiasm and look forward to welcoming you back in the future. Your recommendation means a lot to us.
We had a great vacation and loved this house/property! The house is big with plenty of space for all our gang. We really liked the outdoor space-- all of the decks and the pool with TV and sitting area. We did have some problems with the refrigerator not getting cool enough and the AC on the top floor cutting off, but we had were able to get someone to come and fix things pretty quick. Despite the issues, it was a great place to stay and we'd definitely recommend this place to anyone!
Kelly C.
Stayed 7 nights in Jul 2023
Response from VrboOwner on 21 Dec 2023
Thank you for taking the time to share your wonderful experience with us, Kelly. We are glad you enjoyed the home, pool, and outdoor space. You were terrific guests, and we hope to welcome you all back again!
House was lovely and very convenient to all of our activities!!! I do think the kitchen cabinets and amenities could use some attention and deep cleaning, as they are sticky, well-worn, and for the size of the home, not enough silverware, pots, pans, mixing bowls etc. A keurig coffee maker would be a nice addition to the kitchen as well. However, they do have plenty of dishes, glassware and countertop space!! Pool and outside seating/ dining were all wonderful and well utilized. Bedrooms and bathrooms worked well for all of our folks. The garage fridge never cooled our drinks over the course of the entire week, but the freezer worked perfectly. A work order was called in and may be fixed by now. Overall, we loved the house and will be back!!!
This is our family's second year staying at Caribbean Dream. We feel like it is our home away from home.
We believe this is the best layout for a house we have stayed in since we began visiting Anna Maria in 2006. In the past 13 years, this is the first home we actually stayed in for the second time, because of it's layout, accommodations and proximity to the beach.
Even though we were on vacation, we set our alarm each morning to get up in time to climb the spiral staircase up to the crow's nest to see the sunrise and again at sunset.
There were plenty of chairs, floats and a wagon to carry our supplies down to the beach. We also loved the outdoor shower to rinse off and slip into the hot tub in the early evenings.
There are even additional sleeping accommodations for the extra friends that show up at the last minute.
Dawn H.
Stayed 11 nights in Sep 2019
Response from VrboOwner on 23 Mar 2020
Hi Dawn! Thank you for leaving us a 5 star review! We are so thrilled that you enjoyed your second stay at Caribbean Dream! We are glad that you love the layout and all the amenities this home has to offer! We hope to welcome you back year after year to AMI as our guest!
Verified
8/10 Good
Andreas K.
23 Apr 2018
Perfect stay on AMI.
This house is amazing! It has got everything you need. The location is perfect. All other advantages are mentioned in other reviews.
I'd like to mention some details (ok, it's to complain on a very high level):
This house is equipped with 5 full size beds for 10 adults but has only room for 8 people at the dining table. Same on the terraces. 4 chairs on the 2nd level, 8 on the 3rd and 4 on the top. Therefore you can never eat or sit together. The terraces are leaking, so you can not sit outside when it rains. (luckily it rarely rains ;-)
So enjoy your stay like we did. We will definitely book again.
Andreas K.
Stayed 7 nights in Apr 2018
Response from VrboOwner on 23 Mar 2020
Thank you for letting us know about your stay with Anna Maria Vacations. We we apologize for the lack of timeliness in responding to you ~ Some older reviews have appeared in our system and, even though significant time has passed since your stay with us, we wanted to let you know how much we appreciate your time in reviewing the property you visited. We hope to welcome you back to Anna Maria Island soon!
For a house this size (and the cost) we expected upscale accommodations. Overall, we had a great visit but definitely needs to have a thorough cleaning, new bedding (very worn out), sofas/chairs (also worn out), and a clean washer (very moldy). Pool was great and great proximity to beach without being on a busy street.
janet h.
Stayed 7 nights in Jul 2021
Response from VrboOwner on 10 Aug 2021
Janet, thank you for letting us know about your stay at Caribbean Dream. We are glad you had a great visit and will be sure to pass along your comments to the owners for their consideration in updating the furniture and bedding. We will make sure that the cleaners address the washer when they are at the home next time. We hope that we will be able to welcome you back to AMI soon!
The home was amazing! One block to a very private beach area in AMI and centrally located to enjoy downtown AMI and Holmes Beach areas. The decks are all amazing areas to spend time with family, watch sunsets, do some outdoor yoga, entertain and just find quiet time for peacefulness. The bedroom spaces are all really large, and bathrooms are aplenty. The elevator is a great luxury for hauling groceries to the kitchen too! We loved our stay and made blissful memories!
Sheetal D.
Stayed 7 nights in Jul 2021
Response from VrboOwner on 15 Jul 2021
Sheetal, thank you so much for the very nice review of Caribbean Dream! We think it is an amazing home as well and we are so happy that you all enjoyed your time here on AMI and hope that you will visit us again in the future.
Perfect size vacation home and location was great and close to everything.
David F.
Stayed 7 nights in May 2021
Response from VrboOwner on 19 Jun 2021
David, we are so happy that you enjoyed your stay with us at Caribbean Dream! Thank you for the five-star review. We hope that you will visit us again on your next trip to Anna Maria!
This property was FANTASTIC! We were a five couple family gathering, finally, after COVID restrictions. Had postponed this listing and had to reschedule. VBRO understood our position last year and allowed us to reschedule, keeping previous rates.
Ideally located for the beach. The pool was clean and attended to during our week stay. Plenty of pool toys and wagon for lugging stuff to the beach 1 1/2 blocks away. Ideally located for a family.
Sandy T.
Stayed 7 nights in May 2021
Response from VrboOwner on 1 Jun 2021
Sandy, thank you for the five-star review of Caribbean Dream~ that is always our goal! We are so happy the you and your family had a chance for a post-COVID gathering at this lovely home and hope to be able to welcome you back on your next visit to AMI!
Verified
6/10 Okay
Carrie W.
28 Apr 2021
Liked: Communication, location, listing accuracy
Disliked: Cleanliness
Issues
The house met our expectations for our family, including a short walk to the beach. We were disappointed that the floors were filthy, the grill is out of propane, and garbage was heaped outside in containers for a few days before being picked up.
Carrie W.
Stayed 7 nights in Apr 2021
Response from VrboOwner on 16 May 2021
Carrie, I'm happy that Caribbean Dream met the expectations of your family ~ it is in a great location for beach access! I'm also sorry that you had some issues during your stay with us. I see that you reported the items on around 6:30 on Saturday night and we had the cleaners back to take care of the cleaning and delivered propane on Sunday. It appears that we also removed the trash from the outside bins ~ unfortunately, the houses on the island turn over on Saturdays and trash is picked up by the county on Monday or Tuesday, depending on which city you are staying in. We wish we had control over that, but we don't. We hope that you will come visit Anna Maria Island again in the future.
Verified
8/10 Good
Kelly D.
30 Mar 2021
Liked: Communication, location, listing accuracy
Cruise reimagined
Loved the location, short walk to the beach, layout of the house and heated pool with spa. Elevator was great for groceries and luggage and a recent bad sprained ankle. All balconies had beautiful views. The reason for the overall rating of 4stars is due to the insufficient housekeeping. Floors appeared clean but after walking in bare feet it was apparent the were filthy. Decorative bed pillows and living room pillows were in need of cleaning or replaced. Rocking chair in living room had a dirty head imprint. Table on 3rd deck outside had food residue on it. The grill hadn’t been cleaned in a long time and we cleaned it in order to use it. We had issues with the freezer and electric door lock and both were resolve quickly by management. We did inform management about the cleaning issues after we got home. Had we let property management know, we were assured the problem would’ve been resolved immediately but the group didn’t want to be bothered with a cleaning crew coming in so we made due.
Kelly D.
Stayed 7 nights in Feb 2021
Response from VrboOwner on 30 Mar 2021
Kelly, we are glad that you had an overall good experience at Caribbean Dream. We are so sorry that the cleanliness level wasn't up to your expectations. You are correct, that had we known about the issues, we would have sent the cleaning company back to take care of them for you. We hope that we will be able to welcome you back to our island sometime soon.
Great house for large family. Pool was nice with the young children with us. Great location on the island and close to the beach.
C D.
Stayed 7 nights in Feb 2021
Response from VrboOwner on 1 Mar 2021
CD we appreciate you letting us know about your stay at Caribbean Dream! We think it is a great house and are so happy that you enjoyed your time with us! I agree that you can't beat the location. We would love to have you stay with us the next time you visit AMI!
Our family very much enjoyed our two week holiday stay in this property. The house is even better than the pictures and was exceptionally clean upon arrival. The pool and spa worked flawlessly. Great location for getting into town or walking to the beach and the management agent was extremely responsive. If we had one suggestion, it would be to replace the beach chairs and wagon, which are old and worn out. Other than that, everything was perfect!
Ben P.
Stayed 14 nights in Dec 2020
Response from VrboOwner on 19 Jan 2021
Ben, thank you for letting us know how much you enjoyed your time at Caribbean Dream! We are so happy that your stay was better than expected. We will be sure to pass along your recommendation regarding the beach chairs so that next visit, hopefully all will be perfect!
About the host
Hosted by Anna Maria Vacations
Languages:
English
Premier Host
They consistently provide great experiences for their guests