House in Holmes Beach, FL
6 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Pineapple Cay by Anna Maria Life Vacation Rentals
305 74th St, Holmes Beach, FL 34217
What You'll Love About This Home:
Location! 2.5 Blocks to the Beach!
3 Bed / 3.5 Bath
3 King Beds
Private Heated Pool & Spa
Pool Loungers
Covered Verandah with Patio Dining for 4 (Overlooks Pool)
Gas Grill
Front Balcony with Adirondack Chairs
Keurig & Drip Coffee
Professional Linen Service, Washer & Dryer
Complimentary WIFI
Beach Towels, Chairs & Wagon
Parking for 3 Cars
Details:
Pineapple Cay is located 2.5 blocks from the sugar sand beaches of Anna Maria. Our beach inspired retreat is the ideal vacation home for your family.
The main floor features the living area with access to the covered verandah overlooking the lush tropically landscaped backyard. The kitchen island has counter seating for two and the dining room features a table for six.
The mid-level bedroom includes a king-sized bed, en-suite bathroom and access to the front balcony. The master bedroom and an additional bedroom are located on the second floor and feature king-sized beds and en-suite bathrooms. Each bedroom includes a TV, and crisp linens and plush towels from our professional linen company.
Your guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.
A sparkling, heated pool and spa highlight the backyard which is complete with pool loungers. A covered verandah overlooks the pool and include a high top patio dining table for four and a built-in Coyote gas grill.
Pineapple Cay is easy walking distance to many shops and restaurants, and to the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!
Bedroom 1 - King Bed, Ensuite Bathroom, Balcony Access, TV on Mid-Level
Bedroom 2 - King Bed, Ensuite Bathroom, TV on Floor 2
Bedroom 3 - King Bed, Ensuite Bathroom, TV on Floor 2
Please note:
Pets are not allowed in this home.
Garage is not for guest use
Amenities are subject to change.
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. The minimum requirement for this home is no less than seven nights. The maximum occupancy is six.
VRC16-000123
IMPORTANT INFORMATION:
Your booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.
** Your signed rental agreement must be returned in order to receive your check-in details.
VRBO BOOKINGS
Anna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee.
Your final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance.
The instructions for making your final payment will be included in your final payment reminder.
Please review the cancellation policy prior to booking.
GOOGLE VACATION RENTAL BOOKINGS
Your payment is due in full at the time of booking and the final balance information above does not apply to your reservation.
305 74th St, Holmes Beach, FL 34217
What You'll Love About This Home:
Location! 2.5 Blocks to the Beach!
3 Bed / 3.5 Bath
3 King Beds
Private Heated Pool & Spa
Pool Loungers
Covered Verandah with Patio Dining for 4 (Overlooks Pool)
Gas Grill
Front Balcony with Adirondack Chairs
Keurig & Drip Coffee
Professional Linen Service, Washer & Dryer
Complimentary WIFI
Beach Towels, Chairs & Wagon
Parking for 3 Cars
Details:
Pineapple Cay is located 2.5 blocks from the sugar sand beaches of Anna Maria. Our beach inspired retreat is the ideal vacation home for your family.
The main floor features the living area with access to the covered verandah overlooking the lush tropically landscaped backyard. The kitchen island has counter seating for two and the dining room features a table for six.
The mid-level bedroom includes a king-sized bed, en-suite bathroom and access to the front balcony. The master bedroom and an additional bedroom are located on the second floor and feature king-sized beds and en-suite bathrooms. Each bedroom includes a TV, and crisp linens and plush towels from our professional linen company.
Your guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.
A sparkling, heated pool and spa highlight the backyard which is complete with pool loungers. A covered verandah overlooks the pool and include a high top patio dining table for four and a built-in Coyote gas grill.
Pineapple Cay is easy walking distance to many shops and restaurants, and to the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!
Bedroom 1 - King Bed, Ensuite Bathroom, Balcony Access, TV on Mid-Level
Bedroom 2 - King Bed, Ensuite Bathroom, TV on Floor 2
Bedroom 3 - King Bed, Ensuite Bathroom, TV on Floor 2
Please note:
Pets are not allowed in this home.
Garage is not for guest use
Amenities are subject to change.
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. The minimum requirement for this home is no less than seven nights. The maximum occupancy is six.
VRC16-000123
IMPORTANT INFORMATION:
Your booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.
** Your signed rental agreement must be returned in order to receive your check-in details.
VRBO BOOKINGS
Anna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee.
Your final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance.
The instructions for making your final payment will be included in your final payment reminder.
Please review the cancellation policy prior to booking.
GOOGLE VACATION RENTAL BOOKINGS
Your payment is due in full at the time of booking and the final balance information above does not apply to your reservation.
Amenities at Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals
Non-smoking
No pets allowed
Family friendly
Map of Holmes Beach, FL
Ratings and reviews
10 / 10Outstanding·May 2026
We love Anna Maria Island and the house was perfect. It was super clean and had every amenity you need. They had six beach chairs, an umbrella, beach toys and an awesome wagon to get everything down to the beach. The beach is beautiful and the water is so blue!!
10 / 10Outstanding·Apr 2026
Beautiful home and perfect location! The home was clean and spacious. The pool/hot tub area is stunning. The hot tub heater heats the hot tub in 30 minutes and you could turn it off so it didn’t get too hot. There is an outdoor built in grill and TV on the patio above the pool that we enjoyed cooking at while the kids swam. The landscaping is very well manicured. The owners provided beach towels, beach chairs and a cart. We rented a golf cart using the deal code and never moved our car after we arrived. We were always able to find golf cart beach parking but could have easily walked to the beach if parking had not been available. The beach access close to the home is not crowded and has some of the most gorgeous turquoise water and white sand. The house is located in the center of the island so it was easy to drive the golf cart to all the restaurants as well as Publix, and Walgreens and surf shops. I would highly recommend staying at Pineapple Cay!!
10 / 10Outstanding·Dec 2025
Nice modern house, kids (6 and 7 years-old) loved the pool. Easy walk to the beach was an added plus. Rental company that manages the property gets a 10 out of 10- for communication and follow-up
10 / 10Outstanding·Jun 2025
Beautiful home and pool! We really enjoyed it. Very well stocked and a convenient location. The island is absolutely beautiful! We had a fun and relaxing time! Hated to leave!
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Top rated by guests
9.8Outstanding
(31 Ratings)
"We love Anna Maria Island and the house was perfect. It was super clean and had every amenity you need. They had six beach chairs, an umbrella, beach toys and an awesome wagon to get everything down t..."
Lisa M.Don't miss out! Price and availability may change
