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Sunset Views from Rooftop, Heated Pool, Game Room- Caribbean Dream
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Reviews
9.6 out of 10
Exceptional
5 bedrooms4+ bathroomsSleeps 10241.7 sq m
Popular amenities
Explore the area

Holmes Beach, FL
- Place, Palmetto Avenue Beach4 min walk
- Place, Bradenton Beach5 min walk
- Place, Anna Maria Island Museum and Historical Park3 min drive
- Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)31 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 King Bed
Bedroom 4
1 King Bed
Bedroom 5
1 Queen Bed
Living Room 1
1 Double Sofa Bed
4 bathrooms, 1 half bathroom
Bathroom 1
Bathroom 2
Bathroom 3
Bathroom 4
Half Bathroom 1
Spaces
Porch or lanai
Kitchen
Balcony
About this property
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.
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.
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
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10.0 out of 10, Exceptional, (104 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets 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
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
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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Holmes Beach, FL
What's nearby
- Palmetto Avenue Beach - 4 min walk - 0.4 km
- Bradenton Beach - 5 min walk - 0.4 km
- Island Players - 18 min walk - 1.6 km
- Anna Maria Island Museum and Historical Park - 3 min drive - 2.1 km
- Bean Point Beach - 4 min drive - 2.7 km
Getting around
Restaurants
- The Ugly Grouper - 3 min drive
- Anna Maria Island Beach Cafe - 6 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
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window8.8/10
Cleanliness
9.6/10
Check-in
10/10
Communication
9.8/10
Location
9.6/10
Listing accuracy
Reviews
Verified
30 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Sep 2025
Verified
10/10 Excellent
Christine H.
24 Oct 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Christine H.
Stayed 7 nights in Oct 2025
Verified
10/10 Excellent
Brent G.
10 Apr 2025
Liked: Check-in, communication, location, listing accuracy
Spring break 25
Brent G.
Stayed 7 nights in Mar 2025
Verified
10/10 Excellent
James M.
27 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic Property
James M.
Stayed 7 nights in Jul 2024
Verified
10/10 Excellent
Karen K.
19 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Vacation Home
Karen K.
Stayed 7 nights in Aug 2024
Verified
10/10 Excellent
Alan B.
8 Jan 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Caribbean Dream
Alan B.
Stayed 7 nights in Dec 2023
Verified
10/10 Excellent
Kayce B.
3 Sept 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Caribbean Dream was a dream!
Kayce B.
Stayed 7 nights in Aug 2024
Verified
8/10 Good
Shane T.
3 Aug 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful place
Shane T.
Stayed 7 nights in Jul 2024
Verified
10/10 Excellent
Michael H.
2 Jan 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Dad
Michael H.
Stayed 7 nights in Dec 2024
Verified
10/10 Excellent
Debra K.
22 Dec 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice
Debra K.
Stayed 7 nights in Dec 2024
Verified
10/10 Excellent
Cindy G.
15 Feb 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family get away
Cindy G.
Stayed 7 nights in Feb 2020
Verified
10/10 Excellent
Amber P.
9 Apr 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Relaxing Retreat
Amber P.
Stayed 7 nights in Mar 2025
Verified
10/10 Excellent
Monique F.
7 Mar 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family vacation
Monique F.
Stayed 7 nights in Feb 2020
Verified
10/10 Excellent
Kelly C.
1 Sept 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Anna Maria Vacation
Kelly C.
Stayed 7 nights in Jul 2023
Verified
10/10 Excellent
kim m.
18 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
kim m.
Stayed 7 nights in Jun 2025
Verified
10/10 Excellent
Dawn H.
16 Sept 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Feels like home
Dawn H.
Stayed 11 nights in Sep 2019
Verified
8/10 Good
Andreas K.
23 Apr 2018
Perfect stay on AMI.
Andreas K.
Stayed 7 nights in Apr 2018
Verified
8/10 Good
janet h.
8 Aug 2021
Liked: Check-in, communication, location, listing accuracy
A bit on the light side.
janet h.
Stayed 7 nights in Jul 2021
Verified
10/10 Excellent
Sheetal D.
11 July 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
A dream vacation homeIn AMI
Sheetal D.
Stayed 7 nights in Jul 2021
Verified
10/10 Excellent
David F.
24 May 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely amazing property and location...
David F.
Stayed 7 nights in May 2021
Verified
10/10 Excellent
Sandy T.
16 May 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Reunion
Sandy T.
Stayed 7 nights in May 2021
Verified
6/10 Okay
Carrie W.
28 Apr 2021
Liked: Communication, location, listing accuracy
Disliked: Cleanliness
Issues
Carrie W.
Stayed 7 nights in Apr 2021
Verified
8/10 Good
Kelly D.
30 Mar 2021
Liked: Communication, location, listing accuracy
Cruise reimagined
Kelly D.
Stayed 7 nights in Feb 2021
Verified
10/10 Excellent
C D.
13 Feb 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spot
C D.
Stayed 7 nights in Feb 2021
Verified
10/10 Excellent
Ben P.
19 Jan 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay In Caribbean Dream
Ben P.
Stayed 14 nights in Dec 2020
About the host
Hosted by Anna Maria Vacations
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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