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Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals

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Pool
Pool
Pool
Interior
Living area

Reviews

9.6 out of 10
Exceptional
3 bedrooms3+ bathroomsSleeps 6161.5 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View map
Holmes Beach, FL
  • Place, Bradenton Beach
    ‪4 min walk‬
  • Place, Palmetto Avenue Beach
    ‪6 min walk‬
  • Place, Island Gallery West
    ‪2 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪31 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

King Bedroom 1, TV, Ensuite, 2nd Floor

1 King Bed

King Bedroom 2, TV, Ensuite, 3rd Floor

1 King Bed

King Bedroom 3, TV, Ensuite, 3rd Floor

1 King Bed

3 bathrooms, 1 half bathroom

Half Bath, 2nd Floor

Toilet

King Bathroom 1, Ensuite 2nd Floor

Toilet · Shower only

King Bathroom 2, Ensuite, 3rd Floor

Toilet · Shower only

King Bathroom 3, Ensuite, 3rd Floor

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Dining area

About this property

Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals

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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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. 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.
View more Holiday homes in Holmes BeachOpens in a new window
Map
Holmes Beach, FL

What's nearby

  • Bradenton Beach - 4 min walk - 0.4 km
  • Palmetto Avenue Beach - 6 min walk - 0.5 km
  • Island Gallery West - 2 min drive - 1.8 km
  • Anna Maria Island Museum and Historical Park - 3 min drive - 2.4 km
  • Holmes Beach Beaches - 7 min drive - 2.5 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 31 min drive

Restaurants

  • ‪The Ugly Grouper - ‬17 min walk
  • ‪Anna Maria Island Beach Cafe - ‬5 min drive
  • ‪The Sandbar Restaurant - ‬3 min drive
  • ‪The Waterfront Restaurant - ‬4 min drive
  • ‪Ginny's & Jane E's - ‬18 min walk

Frequently asked questions

Does Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals?

As of 26 Mar 2026, prices found for a 1-night stay for 2 adults at Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals on 23 May 2026 start from AU$571, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals pet-friendly?

No, pets are not allowed at this property.

How much is parking at Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals?

On-site parking is available at the property.

What time is check-in at Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals?

Check-in begins at 4:00 PM.

What time is check-out at Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals?

Checkout is at 10:00 AM.

Where is Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals located?

Situated by the sea, this holiday home is within a 10-minute walk of Bradenton Beach and Palmetto Avenue Beach. Island Players and Island Gallery West are also within 1 mile (2 km).

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 window
Rating 10 - Excellent. 24 out of 28 reviews
Rating 8 - Good. 3 out of 28 reviews
Rating 6 - Okay. 0 out of 28 reviews
Rating 4 - Poor. 1 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

9.0/10

Cleanliness

9.6/10

Check-in

9.6/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Chris F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 13 nights in Nov 2025
Verified

10/10 Excellent

Rhea K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best place ever!

This house was one of our most favorite ever!! Beautiful inside and out, you couldn’t help but relax and enjoy!!
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Rhonda M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Yearly Family Vacation

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!
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

robin m.

Liked: Check-in, communication, location, listing accuracy

Beautiful place

The house was just what we needed, everything we could need was there to use. Great Spot!
Stayed 7 nights in Sep 2024
Verified

10/10 Excellent

Brenda E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Family Vacation

Our stay at Pineapple Cay was wonderful The home is beautiful, clean and walking distance to the beach. The pool and spa are great. Everything we needed was provided. We made lots of wonderful memories.
Stayed 7 nights in Jul 2019
From a partner site

10/10 Excellent

Joe M.

Great Property

This is one of my favorite places to stay on the island. Clean, modern, plenty of space. Bathrooms are all en suite, 3 king beds. The backyard is very private and it's a quick walk to one of the best parts of the beach. Will definitely stay here again.
Verified

4/10 Poor

Jamie H.

Liked: Location
Disliked: Cleanliness, communication, listing accuracy
My family has rented through this company many times before and have always had great experiences, but this last stay was extremely disappointing. The rental was filthy when we arrived…dirty floors, sticky surfaces, moldy showers, dust galore. All clear signs that it hadn’t been properly cleaned in quite some time. I even took photos because it was that bad. After we contacted management, they did send another set of cleaners, but unfortunately, they didn’t do much better. Basic things were still unclean, and we ended up having to wipe down and sanitize areas ourselves just to feel comfortable staying there. What was most frustrating is that the team never followed up afterward to make sure the situation was resolved. We’ve always enjoyed our past experiences, but after this, I’m not sure we’d rent through them again. Cleanliness and communication are basic expectations, and both were severely lacking this time.
All lamps were covered in dust
All light switches were also covered in dust
Sticky surfaces everywhere
Most doors had dark hand print smudges all over
Stayed 7 nights in Oct 2025
Verified

10/10 Excellent

Collison C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pineapple Cay is nice!

Great location (close to both ends) and an easy walk to beach. House is in great condition and had everything we needed. Hot tub was wonderful, pool was a little chilly but it's November, we hated the door alarm though. Needs a bypass. We would book again though! Thanks!
Stayed 7 nights in Oct 2021
Verified

10/10 Excellent

Linda W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Anna Maria trip

Excellent,clean, nicely decorated,stocked with everything you could possibly need,private and quiet,definitely will book again
Stayed 7 nights in Sep 2021
Verified

8/10 Good

Verified traveller

Liked: Check-in, communication, location, listing accuracy

3 Retired Brothers and spouses

The property was fantastic for 3 retired brothers and spouses. The 3 answeet bedrooms worked out perfectly. Had a wonderful stay at Holmes Beach. We will definitely go back and hopefully get the same place.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

laura h.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very comfortable

Pineapple Cay is a beautiful property. The bedrooms are very comfortable and the home is quite spacious. The pool area is wonderful and the gorgeous Anna Maria beach is a 3 minute bike ride away. We really enjoyed our stay!
Stayed 23 nights in Dec 2020
Verified

10/10 Excellent

Ashley B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great week at the beach

This place was a prefect get away for my family of four over Christmas break. The house had everything we needed and was adorable! Will definitely be back!
Stayed 7 nights in Dec 2020
Verified

10/10 Excellent

Yamileydi G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent!!!

Excellent location!!
Stayed 7 nights in Aug 2020
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Vacation Destination

Our family of 5 enjoyed our stay at this awesome home during the middle of July. We spent some time each day hanging out at the beautiful beaches nearby, and cooling off at the pool when at the house. We found plenty of options for food nearby, and really enjoyed our stay. We are all looking forward to our next visit!
Stayed 7 nights in Jul 2019
Verified

8/10 Good

Colleen C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home!

The house was beautiful and clean and we loved the pool and the short walk to the beach. The only reason for the 4 stars is that the mattresses were saggy as well as the sofa couch and this resulted in back soreness even from our 20 year olds. Otherwise, it was a perfect vacation home and we would rent from here again! Everyone was friendly and accommodating!
Stayed 7 nights in Jun 2019
Verified

10/10 Excellent

Doug Z.

AWESOME!

Great house...very spacious!! hot tub and pool was perfect. Great location to the beach. Maint. came right away when we needed more propane, ice maker issue and water pressure in bathroom was low. house was super clean check in and check out was SIMPLE!!! beach chairs and coolers that the house provided was so helpful a wagon would be a plus! I would recommend this house and location! we will be back.
Stayed 7 nights in May 2019
Verified

10/10 Excellent

Brenda D.

Pineapple cay

Beautiful place. Loved everything about it!!!
Stayed 7 nights in Apr 2019
Verified

10/10 Excellent

Holly H.

Fabulous. Three bedroom house great. Everything we wanted. Beach close by.

Loved the deco of the house. Beautiful house. Loved pool and hot tub. Beach was great for swimming and sunsets. Shopping great. Food great on the island. Had fun riding the trolley. Enjoyed are stay.
Stayed 7 nights in Feb 2019
Verified

10/10 Excellent

Michael G.

Exceptional Property

This is an exceptional property. We had a wonderful time.
Stayed 7 nights in Jan 2019
Verified

8/10 Good

Karen N.

Beautiful home with lovely pool and hot tub. Only disappointment was the filthy outdoor grill.

We like that all bedrooms had king beds. Beautiful interior. The hot tub and pool came in handy due to the cool weather we had. Only downfall was the patio grill was filthy and unusable.
Stayed 7 nights in Jan 2019
Verified

10/10 Excellent

Judith H.

Great time!!

Everything was exceptionally clean except for the grill. We had to fill the propane, which made our guests wait for dinner. I would have liked a lighter blanket, the comforter was very warm. I would definitely stay there again.
Stayed 7 nights in Dec 2018
Verified

10/10 Excellent

praveenbs07

Pineapple cay is one of our favorite place now. Very clean and modern. Enjoyed hot tub and pool.

Staying at Pineapple cay was a pleasant experience even though weather was not that great when we were visting. Hot tub and pool kept us engaged, enjoyed every bit. Property manager and owners were friendly, ensured to make our stay comfortable & pleasant. Beach access is just few steps away. We highly recommend this place. Hope to visit again soon.
Stayed 7 nights in Dec 2018
Verified

10/10 Excellent

Barbara K.

VERY NICE!

This house is so nice!!! Very well decorated, great location, clean and beautiful back yard. We have stayed on the island many times and this was one of our favorites!!!
Stayed 7 nights in Oct 2018
Verified

10/10 Excellent

LINDA H.

We Loved This Rental!

This house was clean as a whistle, and beautifully decorated. A lot of helpful things were provided that we would have had to purchase (dish detergent, dishwasher detergent, laundry detergent, hand soap in all the bathrooms, thank you!). Lots of beach towels and bath towels were also provided. The beds were so comfortable and it was nice to have king size beds in all three rooms. Red tide was still an issue the week we were there, so we were glad to have the pool and hot tub. Mid-week the red tide had settled down and we were able to swim at the beach as well, and the walk from the house was an easy one. We would definitely rent this place again!
Stayed 7 nights in Sep 2018
Verified

10/10 Excellent

Mark B.

Amazing home with everything you could ask for!

We loved our stay and will definitely be back again! The home was beautiful inside and out and we had everything we needed for our weeks stay at Anna Maria Island! From the pool and the hot tub, to the spacious bedrooms, kitchen and living room, our stay was phenomenal. Thank you for an awesome experience!
Stayed 7 nights in Jul 2018

About the host

Hosted by Anna Maria Life Vacation Rentals

Host profile image
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 luxury six-bedroom pool home. AMLVR's vacation rentals offer authentic island living in paradise!

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