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

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A swimming pool with a curved design, surrounded by a tiled deck and outdoor furniture.
A two-story house with a balcony, a garage, and a well-maintained lawn.
A bedroom with a bed, a ceiling with a blue accent, a wall-mounted painting, and a window with blinds.
A spacious living room with a large TV, wicker furniture, and a chandelier.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, two bar stools, and pendant lighting.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms4 bathroomsSleeps 6162 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
    ‪3 min drive‬
  • Place, Anna Maria Island Museum and Historical Park
    ‪3 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪38 min drive‬

Room options

About the area

Holmes Beach

At this holiday home you'll be within a 20-minute stroll of Bradenton Beach and Palmetto Avenue Beach. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .You can enjoy Smart televisions with a DVD player, and home features free WiFi, 3.5 bathrooms and a balcony. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A fenced private garden, a TV and a coffee/tea maker are also available. .Attractions within a 10-minute drive of this Holmes Beach holiday home include Bean Point Beach and Anna Maria Beach.
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What's nearby

  • Bradenton Beach - 4 min walk - 0.4 km
  • Island Players - 3 min drive - 2.1 km
  • Palmetto Avenue Beach - 3 min drive - 2.1 km
  • Anna Maria Island Museum and Historical Park - 3 min drive - 2.4 km
  • Tampa Bay - 39 min drive - 38.2 km

Getting around

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

Restaurants

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Pineapple Cay by Anna Maria Life Holiday 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, Washing machine & 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 holiday 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 washing machine 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 holiday!

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 holidaying in a residential area. Please be a good neighbour 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 Holiday 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 Holiday 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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Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Fenced yard
  • Gas grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near a zoo
  • Near an outlet shopping centre
  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Parasailing nearby
  • Rafting nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Theme park nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 1,738 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events 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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a deadbolt lock in all accommodation.

Property is also known as

752710

Frequently asked questions

Are there any beaches close to Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals?

Yep, Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals is a short 6-minute walk from Bradenton Beach. Fun beach activities include jet skiing, snorkelling and scuba diving. You can also find motor boats.

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

Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals has a heated pool and a pool.

What makes Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals a romantic place to stay?

1 hot tub, private pools, and private balconies all help set the scene for a sizzling getaway at Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals.

Is there a private hot tub at Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals?

Yep, there is a hot tub.

Is there a free airport shuttle available at Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals?

No, Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Pineapple Cay: 2.5 Blocks to Beach! Pool & Spa by Anna Maria Life Vacation Rentals?

No, pets are not allowed.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 29 out of 33 reviews
Rating 8 - Good. 3 out of 33 reviews
Rating 6 - Okay. 0 out of 33 reviews
Rating 4 - Poor. 1 out of 33 reviews
Rating 2 - Terrible. 0 out of 33 reviews

9.2/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean rooms great experience clean well maintained house.
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!!
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!!
Stayed 7 nights in Apr 2026
Verified review

4/10 Poor

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Excellent!!!

Excellent location!!
Stayed 7 nights in Aug 2020
Verified review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

Pineapple cay

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

10/10 Excellent

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 review

10/10 Excellent

Exceptional Property

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

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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

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