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

Holmes Beach, Florida
$340 avg/night
Bed 3

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

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.
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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.

Read More Expand
  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1738 Sq Ft (162 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Fenced Yard Gas Grill
  • POOL/SPA

    Heated Pool Hot Tub Private Pool
  • BATHROOMS

    3.5 Bathrooms Hair Dryer Shower Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Birdwatching Nearby Ecotours Nearby Hiking Nearby Hiking/biking Trails Nearby Kayaking Nearby Marina Nearby Sailing Nearby Theme Parks Nearby
  • ENTERTAINMENT

    Books DVD Player Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near A Hospital Near A Zoo Near Outlet Shopping Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Chris F.

    Submitted Dec 15, 2025

    Stayed Nov 30, 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

  • Jamie H.

    Submitted Oct 29, 2025

    Stayed Oct 18, 2025

    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.

  • Rhonda M.

    Submitted Jun 29, 2025

    Stayed Jun 21, 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!

  • Rhea K.

    Submitted Jun 18, 2025

    Stayed Jun 7, 2025

    This house was one of our most favorite ever!! Beautiful inside and out, you couldn’t help but relax and enjoy!!

  • robin m.

    Submitted Sep 17, 2024

    Stayed Sep 7, 2024

    The house was just what we needed, everything we could need was there to use. Great Spot!

  • Joe M.

    Submitted Nov 15, 2023

    Stayed Dec 31, 1969

    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.

  • Collison C.

    Submitted Nov 8, 2021

    Stayed Oct 30, 2021

    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!

  • Linda W.

    Submitted Sep 11, 2021

    Stayed Sep 4, 2021

    Excellent,clean, nicely decorated,stocked with everything you could possibly need,private and quiet,definitely will book again

  • Submitted Aug 11, 2021

    Stayed Jul 24, 2021

    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.

  • laura h.

    Submitted Jan 24, 2021

    Stayed Dec 17, 2020

    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!

Your dates are Available!

Total

Includes taxes and fees
$340+
View details