Entire home
Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life
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Reviews
9.0 out of 10, Loved by Guests
Top 10% of guest reviews in this area
4 bedrooms4+ bathroomsSleeps 8254.9 sq m
Popular amenities
Explore the area

Holmes Beach, FL
- Place, Palmetto Avenue Beach6 min walk
- Place, Bradenton Beach6 min walk
- Place, Island Players18 min walk
- Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)31 min drive
Rooms & beds
4 bedrooms (sleeps 8)
Bunk Bedroom with 4 Twin Beds, TV, 2nd Floor
2 Single Bunk Beds
King Bedroom 1, TV, Ensuite, 2nd Floor
1 King Bed
King Bedroom 2, TV, Ensuite, 2nd Floor
1 King Bed
King Bedroom, TV, 2nd Floor
1 King Bed
4 bathrooms, 1 half bathroom
Guest Bathroom 1, 2nd Floor
Toilet · Shower only
Guest Bathroom 2, 2nd Floor
Bathtub or shower · Toilet
Half Bathroom 5
Toilet · Shower only
King Bathroom 1, Ensuite, Dual Sinks, 2nd Floor
Bathtub · Toilet · Shower only
King Bathroom 2, Ensuite, 2nd Floor
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Garden
Dining area
About this property
Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life
Island Pineapple by Anna Maria Life Vacation Rentals
404 80th Street, Holmes Beach, FL 34217
What You'll Love About This Home:
Location! 5 Minute Walk to the Beach!
4 Bedrooms / 4 Bathrooms
3 King Beds / 2 Sets of Twin over Twin Bunkbeds
Private, Heated, Screened Pool with Waterfalls & Ambient Lighting
Wrap Around Balcony Overlooking Pool
Covered Lanai with Outdoor Seating
Outdoor Kitchen with Gas Grill & TV
Whole Home Air Purification System
Professional Linen Service and Washer & Dryer
Complimentary WIFI
Beach Towels, Chairs, Wagon
Parking for 5 Cars
Details:
Island Pineapple will delight the beach vacation in you! Located a quick, five minute walk to the sugar sand beaches of Anna Maria, our home is made for vacation!
With the main living space on the second floor and many oversized windows, the home is bathed in natural light. Have the chef in your family create your favorite meal in the modern kitchen. The large breakfast bar and open dining area provide ample space for everyone to dine together. Outdoor dining is also an option on the covered lanai with patio seating.
The bedrooms are all located on the second level and have access to the wrap around balcony overlooking the pool. The master has a king sized bed, en-suite bathroom and views of the pool deck. Two of the guest rooms have king beds with the third guest room with two sets of twin over twin bunkbeds. Two of the king guest rooms have an ensuite bathroom. Each of the bedrooms features a TV. Guests will enjoy 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.
The main level of Island Pineapple is for fun! A kitchenette with BBQ grill and outdoor patio dining set make poolside meals easy! The large private screened-in heated pool features 3 waterfalls, ambient lighting, and in-pool seating.
After a day soaking up the sun at the beach, the sparkling heated pool welcomes you home with three waterfalls, ambient lighting, and in-pool seating, all under the comforts of a pool screen.
A bonus highlight of Island Pineapple is the whole home air purification system designed to disinfect the air by neutralizing airborne pathogens including bacteria and viruses.
Island Pineapple is easy walking distance 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. Island Pineapple is the perfect location for your next beach vacation.
This home is dog friendly with a pet fee of $150 plus tax per dog. If you have added a pet to your reservation, the fee including tax ($168) has been included in your total.
All Bedrooms are on the 2nd Floor (main living level)
Master Bedroom: King Bed with Ensuite Bathroom
Second Bedroom: King Bed with Ensuite Bathroom
Third Bedroom: King Bed
Fourth Bedroom: Two Sets of Twin over twin Bunkbeds
Please note:
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 eight.
VRC19-000013
Golf Cart DEAL ALERT!!!
Reserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.
FUN way to explore the island for the entire family.
Mention Anna Maria Life Vacation Rentals and receive this VIP deal!
www.FunAndMoreRentals.com
941-462-2719
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.
404 80th Street, Holmes Beach, FL 34217
What You'll Love About This Home:
Location! 5 Minute Walk to the Beach!
4 Bedrooms / 4 Bathrooms
3 King Beds / 2 Sets of Twin over Twin Bunkbeds
Private, Heated, Screened Pool with Waterfalls & Ambient Lighting
Wrap Around Balcony Overlooking Pool
Covered Lanai with Outdoor Seating
Outdoor Kitchen with Gas Grill & TV
Whole Home Air Purification System
Professional Linen Service and Washer & Dryer
Complimentary WIFI
Beach Towels, Chairs, Wagon
Parking for 5 Cars
Details:
Island Pineapple will delight the beach vacation in you! Located a quick, five minute walk to the sugar sand beaches of Anna Maria, our home is made for vacation!
With the main living space on the second floor and many oversized windows, the home is bathed in natural light. Have the chef in your family create your favorite meal in the modern kitchen. The large breakfast bar and open dining area provide ample space for everyone to dine together. Outdoor dining is also an option on the covered lanai with patio seating.
The bedrooms are all located on the second level and have access to the wrap around balcony overlooking the pool. The master has a king sized bed, en-suite bathroom and views of the pool deck. Two of the guest rooms have king beds with the third guest room with two sets of twin over twin bunkbeds. Two of the king guest rooms have an ensuite bathroom. Each of the bedrooms features a TV. Guests will enjoy 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.
The main level of Island Pineapple is for fun! A kitchenette with BBQ grill and outdoor patio dining set make poolside meals easy! The large private screened-in heated pool features 3 waterfalls, ambient lighting, and in-pool seating.
After a day soaking up the sun at the beach, the sparkling heated pool welcomes you home with three waterfalls, ambient lighting, and in-pool seating, all under the comforts of a pool screen.
A bonus highlight of Island Pineapple is the whole home air purification system designed to disinfect the air by neutralizing airborne pathogens including bacteria and viruses.
Island Pineapple is easy walking distance 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. Island Pineapple is the perfect location for your next beach vacation.
This home is dog friendly with a pet fee of $150 plus tax per dog. If you have added a pet to your reservation, the fee including tax ($168) has been included in your total.
All Bedrooms are on the 2nd Floor (main living level)
Master Bedroom: King Bed with Ensuite Bathroom
Second Bedroom: King Bed with Ensuite Bathroom
Third Bedroom: King Bed
Fourth Bedroom: Two Sets of Twin over twin Bunkbeds
Please note:
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 eight.
VRC19-000013
Golf Cart DEAL ALERT!!!
Reserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.
FUN way to explore the island for the entire family.
Mention Anna Maria Life Vacation Rentals and receive this VIP deal!
www.FunAndMoreRentals.com
941-462-2719
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.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
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9.6 out of 10, Exceptional, (33 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
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
About the area
Holmes Beach
Located in Holmes Beach, this holiday home is near theme parks and near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Looking to enjoy an event or a game while in town? See what's happening at LECOM Park or IMG Bollettieri Tennis Academy. 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 - 6 min walk - 0.6 km
- Bradenton Beach - 6 min walk - 0.6 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
9.0
Wonderful
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.4/10
Cleanliness
9.8/10
Check-in
9.6/10
Communication
10/10
Location
9.6/10
Listing accuracy
Reviews
8 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in May 2025
10/10 Excellent
Katherine R.
24 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay
Katherine R.
Stayed 7 nights in Jun 2023
10/10 Excellent
Jeffrey S.
16 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice place
Jeffrey S.
Stayed 7 nights in Jul 2022
10/10 Excellent
Jordan S.
19 Feb 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay
Jordan S.
Stayed 7 nights in Feb 2024
10/10 Excellent
Barbara C.
23 July 2022
Liked: Cleanliness, check-in, location, listing accuracy
Family vacation
Barbara C.
Stayed 7 nights in Jul 2022
10/10 Excellent
Veronica S., Brookfield, Wisconsin
3 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Island Pineapple - Bliss
Veronica S.
Stayed 7 nights in Mar 2023
10/10 Excellent
WPZ22
6 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
The Host Services were Excellent
WPZ22
Stayed 7 nights in Aug 2023
10/10 Excellent
Michael P.
25 Jan 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Anna Maria Pineapple House
Michael P.
Stayed 14 nights in Jan 2024
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Patricia R.
24 Mar 2024
Pineapple House
Patricia R.
10/10 Excellent
PAUL C.
18 Aug 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous.
PAUL C.
Stayed 7 nights in Aug 2023
10/10 Excellent
Jamie N.
7 Mar 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
AMAZING
Jamie N.
Stayed 7 nights in Feb 2021
8/10 Good
André B.
26 Dec 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Spacious and beautiful house in the best location
André B.
Stayed 7 nights in Nov 2022
This review is from a guest who booked and stayed through a partner site and can't be verified.
8/10 Good
Christie A.
10 June 2024
Location is perfect! House is wonderful-Just needs attention to a few things.
Christie A.
4/10 Poor
Jay P., ohio
1 Jan 2023
Liked: Cleanliness, check-in, communication, location
Beauty is Only Skin Deep
Jay P.
Stayed 14 nights in Dec 2022
8/10 Good
Virginia G.
3 June 2021
Liked: Check-in, communication, location, listing accuracy
May 2021
Virginia G.
Stayed 14 nights in May 2021
This review is from a guest who booked and stayed through a partner site and can't be verified.
6/10 Okay
Catherine S.
10 July 2023
3 Stars
Catherine S.
This review is from a guest who booked and stayed through a partner site and can't be verified.
6/10 Okay
Catherine S.
10 July 2023
3 Stars
Catherine S.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Gail R.
25 Jan 2023
Wonderful Rental Experience!
Gail R.
This review is from a guest who booked and stayed through a partner site and can't be verified.
6/10 Okay
Jeanne B.
19 Nov 2022
Island pineapple stay
Jeanne B.
10/10 Excellent
Verified traveller
6 Mar 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful just beauiful
Verified traveller
Stayed 7 nights in Feb 2022
10/10 Excellent
Darren N.
21 July 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay at Island Pineapple
Darren N.
Stayed 7 nights in Jul 2021
10/10 Excellent
Karen H.
12 Oct 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful
Karen H.
Stayed 7 nights in Sep 2020
10/10 Excellent
mildred p.
13 Aug 2019
Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness
Necesitaba mas limpieza
mildred p.
Stayed 7 nights in Jul 2019
About the host
Hosted by Anna Maria Life Vacation Rentals
Family-owned and operated, Anna Maria Life Vacation Rentals offers everything you are looking for in an Anna Maria Island vacation rental company – exceptional properties and quality service with a personal touch. Whether it's a family vacation or a romantic getaway, AMLVR has something for everyone. From beachfront to bayside, you can choose from a quaint one-bedroom cottage, a waterfront condo with stunning views of the Gulf of Mexico, or a six bedroom pool home. AMLVR's vacation rentals offer authentic island living at an affordable price. Accommodations can be as upscale or as casual as you like and most are pet-friendly so you won't have to leave your furry family member at home.
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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