Caribbean Dream Vacation Rental With 5 Bedroom a Private Pool and Rooftop Deck on Anna Maria Island, FL

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!


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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.