Home 5+ Bedroom Vacation Rentals In Anna Maria, FL

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Exceptional(4)

$1242.56

/ Nightly
Private Vacation Home

Rooftop Deck, Private Pool and Game room! Perfect for Families!

Anna Maria, Florida, United States

Boundless Waves by Exclusive Vacations brVR24-000005 brbrWelcome to Boundless Waves, part of our Exclusive Collection. Offering a curated luxury experience with elevated amenities, personalized services, and refined island living. This six-bedroom, six-and-a-half-bath coastal retreat features a rooftop deck with panoramic island views, a resort-style pool and spa. Thoughtfully designed interiors, created for those who expect only the best on their Anna Maria Island getaway! brbrHighlights br• Exclusive Collection luxury home br• 8-minute walk to the Gulf beaches br• Resort-style pool with in-ground spa and sun shelf loungers br• Rooftop deck with island and sunset views br• Covered outdoor living and dining areas br• Game room with ping pong and air hockey br• Chef’s kitchen with premium appliances and gold accents br• Multiple furnished balconies br• 4 Parking Spaces br• Washer/dryer br• Pet friendly with approval and fee brbrExclusive Amenities: br• 6 Seat Club Car Cru Golf Cart for Guest Use br• Luxury Beach Bikes for Guest Use br• Luxury Beach Chairs and a Beach Cart for Guest Use br• Upgraded Bed and Bath Linens and Toiletries br• Portable Pack and Play brbrThe resort-style pool is the heart of the home, complete with in-water loungers, spa, and lush tropical landscaping. Relax under the shaded lanai with cozy seating or dine al fresco by the pool. End each evening on the rooftop deck with breathtaking island sunsets and starlit skies. brbrStep into a sun-filled sanctuary with vaulted ceilings, curated coastal decor, and expansive windows. The living room features plush seating, a smart TV, and balcony access. The chef’s kitchen is a showpiece with premium appliances, quartz countertops, and an oversized island, perfect for entertaining. Gather in the dining area for meals shared in style. brbrThis home offers a stunning primary bedroom with a King bed, luxury furnishings, and an ensuite bathroom with a double vanity and a walk-in shower. Four King bedrooms are appointed with crisp linens, TVs, storage space, and an ensuite bathroom. The sixth bedroom was designed for the younger guests of the group, with a day bed and in the hallway is a bathroom with a shower and tub combination. Each bedroom offers a private oasis with luxury bedding, ample storage, and spa-like bathrooms. The home is designed to accommodate families and groups with ease, blending comfort with elegance. brbrRoom Details br• Primary Bedroom: King bed, ensuite bath with walk-in shower and double vanity br• Second Bedroom: King bed, ensuite bath with walk-in shower br• Third Bedroom: King bed, ensuite bath with walk-in shower br• Fourth Bedroom: King bed, ensuite bath with walk-in shower br• Fifth Bedroom: King bed, ensuite bath with walk-in shower br• Sixth Bedroom: Twin daybed, access to hall bath with shower/tub combo brbrIdeally located in the heart of Anna Maria, Boundless Waves is just minutes from Home, The Center of Anna Maria Island, Gulf beaches, the AMI Historical Society, City Pier, and the boutiques and dining along Pine Avenue. Explore the island with ease by bike, golf cart, or the free trolley. brbrExperience the pinnacle of Anna Maria Island luxury at Boundless Waves, an Exclusive Collection home. Book your stay today and discover the ultimate island escape. br brbr- brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. brbr4 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. brbrUse of the provided golf cart requires the driver to maintain a current U.S. automobile insurance. Proof of insurance is required upon request.brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Island Accommodations Rental Policies for full details. brbrWe 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. brbrPlease see our Anna Maria Island Accommodations Rental Policies for full details. brbrPlease 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.
Bed 6

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Bath 6

Bath

Sleep 8

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Exceptional(65)

$867.04

/ Nightly
Private Vacation Home

Luxury AMI Home - Heated Pool & Spa - Steps to Beach - Ocean Views

Anna Maria, Florida, United States

• Custom-built 5BR/4.5BA retreat on Anna Maria Island’s quiet North Shore—just one house from the beach!brbr • Gorgeous ocean views from the porch—perfect for morning coffee or sunset cocktailsbrbr • Private heated pool & spa in a shaded backyard oasisbrbr • Spacious 3,200 sq. ft. layout—ideal for families and groupsbrbr • Professionally decorated with wood floors, marble countertops, stainless appliances, and custom cabinetrybrbr • Dining table seats 10 for memorable group gatheringsbrbr • 5 King bedrooms: Primary suite w/ private bath & shower on 3rd floor near kitchen/living; 4 guest rooms on 2nd floor (2 ensuite, 1 Jack & Jill)brbr • Crib, Pack & Play, and high chair provided for familiesbrbr • Elevator access to all levelsbrbr • Grill at home or dine at local restaurants just blocks awaybrbr • Enhanced security: driveway/pool gate cameras (no interior surveillance)brbr • No hidden fees—our rates are all-inclusive!brbrBook your Anna Maria Island escape—luxury, comfort, ocean views, and only steps from the sand!
Bed 5

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Bath 4

Bath

Sleep 10

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Exceptional(32)

$1333.9

/ Nightly
Private Vacation Home

On the Beach Block! Luxury home, Pool and Spa, stay and relax with your friends!

Anna Maria, Florida, United States

Villa La Concha by Anna Maria Island AccommodationsbrVR16-000446brbrWelcome to Villa La Concha, a luxurious six-bedroom, four-and-a-half-bath vacation rental just a one minute from the white sands of Anna Maria beach! Perfect for large families or groups, this coastal retreat features a private pool and hot tub, game room, and multiple outdoor entertaining areas. Whether you’re here to relax poolside, explore Pine Avenue’s shops and restaurants, or enjoy Gulf Coast adventures, this home is designed for the ultimate Anna Maria Island getaway.brbrHighlightsbr• 1-minute/ 7 houses to Anna Maria beachbr• 6 Bedrooms / 4.5 Bathroomsbr• 5 King beds, 1 Twin-over-Twin bunk bedbr• Private heated pool with hot tub and swim-up tablebr• Game room with Ping Pong and Foosballbr• BBQ grill and outdoor dining areabr• Multiple balconies with seatingbr• Parking for 4 vehiclesbr• Washer and dryerbrbrStep outside to your private tropical oasis. The heated pool includes a fun swim-up table and a bubbling hot tub, perfect for relaxing after a day at the beach. The covered patio offers plush seating, outdoor dining, TV, and a BBQ grill for unforgettable family meals al fresco. Indoors, the game room keeps the fun going with Ping Pong, Foosball, and classic games for guests of all ages.brbrThe home’s open and airy design creates a welcoming atmosphere with abundant natural light. The living room is furnished with cozy seating and TV, ideal for family movie nights. The modern kitchen comes fully equipped with stainless steel appliances, plenty of cabinet space, and all the cookware and utensils needed to prepare group meals. A large dining table brings everyone together for meals.brbrThe primary suite is a private retreat with a king bed, ensuite bathroom with double vanity and walk-in shower, and a private balcony for morning coffee or evening breezes. Two additional king bedrooms on the second floor each include ensuite baths with walk-in showers, and one also features a private balcony. The third floor offers two more king bedrooms, plus a twin-over-twin bunk room that’s perfect for kids, along with a hallway bathroom with a shower/tub combo.brbrRoom Detailsbr-Primary Bedroom, 3rd Floor: King bed, private balcony, ensuite bathroom with double vanity and walk-in showerbr-Second Bedroom, 2nd Floor: King bed, balcony, ensuite bathroom with walk-in showerbr-Third Bedroom, 2nd Floor: King bed, ensuite bathroom with walk-in showerbr-Fourth Bedroom, 3rd Floor: King bedbr-Fifth Bedroom, 3rd Floor: King bedbr-Sixth Bedroom, 3rd Floor: Twin-over-Twin bunkbrbrThis home also includes Wi-Fi, multiple balconies with seating, a washer and dryer, and an outdoor shower to rinse off after beach days. With a central location near Anna Maria beach and just minutes from Pine Avenue’s shops and restaurants, guests can easily explore the island by bike or hop on the AMI trolley.brbrWith its private pool and spa, spacious game room, and prime location near Anna Maria beach and Pine Avenue, Villa La Concha is the ultimate vacation rental for families and groups. Book your stay today with Anna Maria Island Accommodations and experience the perfect blend of fun, comfort, and island luxury!brbrbr-br*Please note: This home is strictly an animal-free zone due to severe allergies. Due to this homeowner allergy, we are unable to welcome any animals including service and/or emotional support animals. brbr*Please note: 4 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.brbrThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company.brbrWe 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.brPlease see our Anna Maria Island Accommodations Rental Policies for full details.brbrPlease Remember:brYou 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.br*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Bed 6

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Bath 4

Bath

Sleep 12

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Home Most popular vacation rentals in Anna Maria

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Exceptional(32)

$2162.54

/ Nightly
Private vacation home

Elegance~Gorgeous! Arcade!~ Heated pool/spa~North End!

Anna Maria, Florida, United States

Bed 7

Bed

Bath 7

Bath

Sleep 14

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Exceptional(32)

$2397.49

/ Nightly
Apartment

Cloud 9 - BeachFront Splendor

Anna Maria, Florida, United States

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Bath 6

Bath

Sleep 8

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Exceptional(32)

$2381.19

/ Nightly
Private vacation home

NEW! Meet Me At Sunset! 3 Homes from the Beach!

Anna Maria, Florida, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

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Exceptional(32)

$2367.68

/ Nightly
Private vacation home

Beachfront Home | Pool + Spa | Games | Ocean Views

Anna Maria, Florida, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

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Exceptional(32)

$2337.14

/ Nightly
Private vacation home

Palmetto Paradise~Heated Pool/Spa, Steps to the Beach!

Anna Maria, Florida, United States

Bed 4

Bed

Bath 5

Bath

Sleep 8

Sleeps
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Exceptional(32)

$1926.55

/ Nightly
Private vacation home

Sundowner Beach: Luxury Gulf-front, stunning views

Anna Maria, Florida, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(32)

$1888.73

/ Nightly
Private vacation home

Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak, SUPs & MORE

Anna Maria, Florida, United States

Bed 5

Bed

Bath 5

Bath

Sleep 14

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Exceptional(32)

$1896.38

/ Nightly
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Snook Lookout: Canal Home, Pool, Game Room, Putting Green by Anna Maria Life Vacation Rentals

Anna Maria, Florida, United States

Bed 5

Bed

Bath 5

Bath

Sleep 8

Sleeps
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Exceptional(32)

$2431.03

/ Nightly
Private vacation home

NEW! Blue Crush! Steps to the beach! Heated Pool!

Anna Maria, Florida, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(32)

$1989.44

/ Nightly
Private vacation home

Summer Strand Resort like pool, close to beach, kayak w/ manatees, Rooftop Deck

Anna Maria, Florida, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

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