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Pineapple Cottage: Pet Friendly 4 Bedroom Vacation Home For Rent Anna Maria Florida

Home Rental in Anna Maria Florida

This excellent vacation rental in Anna Maria, Florida oozes comfort with its 4 bedrooms and a private pool. Enjoy with the family, accommodates pets, alongside facilities such as a grill, TV, and internet.

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Salty Mermaid Real Estate & Vacation Rentals
Connect directly with the local vacation rental manager.
Rates from
$475 / night
Additional fees may apply
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Rental overview

Why You'll Love This Rental

Pineapple Cottage is a 4-bedroom, 3-bath ground-level home in Anna Maria, Florida that sleeps up to 8. Set in a waterfront-nearby area and near a beach (listed at 0.3 miles), it pairs a central in-town location with a private outdoor setup that includes a saltwater pool and spa. The home was restored after hurricanes Helene and Milton, and it uses keyless entry via a keypad.

Inside, the bedroom mix includes two king rooms, one queen room, and a trundle bed. Everyday conveniences include air conditioning, ceiling fans, Wi-Fi, TVs, towels/linens, and a washer/dryer. The kitchen is equipped with a refrigerator, freezer, microwave, dishwasher, coffee maker, and blender, and there’s a grill for outdoor cooking. Parking is provided (driveway parking for two vehicles side by side, plus an additional spot noted). Some pets are allowed, with dog size and fee details provided in the house rules. Pool-area doors and windows have required audible alarms, and a Ring door camera is installed at the front entrance.

Good fit for
Pet-friendly stays Beach trips
Private Pool and Spa Includes a private saltwater pool and hot tub/spa on the property.
Sleeps Eight Four bedrooms and three full baths accommodate up to 8 guests.
Near the Beach Beach distance is listed at 0.3 miles.
Dog Friendly Option Dogs 25 lbs or less are allowed with a separate per-pet fee.
Keyless Entry Keypad entry is provided for access.
At a glance

Property Highlights

Waterfront - NearbyLocation Setting
Near a BeachBeach Access
4 BedroomsBedrooms
3 Full BathroomsBathrooms
Sleeps 8Guest Capacity
Pool (Private)Pool
Internet AccessInternet
TelevisionTelevision
YesAir Conditioning
YesPet Friendly
YesWasher / Dryer
Location & nearby Explore the Area

Pineapple Cottage is located in Anna Maria City in Anna Maria, Florida, with a location setting listed as waterfront-nearby and near a beach (0.3 miles). The source information places it in the heart of the city and notes it is one block from Pine Avenue, where shops and restaurants are located. A free island trolley stop is also noted on Pine Avenue. Parking guidance is provided for the driveway and an additional grass-strip space in front of the home.

Plan your stay

Rates & Availability (USD)

Rates from
$475 per night
4-day minimum stay
Check current rates & availability

Live booking details are maintained by Salty Mermaid Real Estate & Vacation Rentals.

Check Availability

Availability Calendar

Use the calendar as a guide, then confirm current availability directly with the manager.

Available Booked
Season Nightly Weekly Monthly
PMS Rate
Oct 30, 2026 - Oct 30, 2026
Minimum Stay: 4 Days
$475 $3,346 n/a
PMS Rate
Oct 31, 2026 - Oct 31, 2026
Minimum Stay: 4 Days
$475 $3,397 n/a
PMS Rate
Nov 01, 2026 - Nov 01, 2026
Minimum Stay: 4 Days
$475 $3,454 n/a
PMS Rate
Nov 02, 2026 - Nov 04, 2026
Minimum Stay: 4 Days
$475 $3,490 n/a
PMS Rate
Nov 05, 2026 - Nov 05, 2026
Minimum Stay: 4 Days
$496 $3,498 n/a
PMS Rate
Nov 06, 2026 - Nov 06, 2026
Minimum Stay: 4 Days
$526 $3,540 n/a
PMS Rate
Nov 07, 2026 - Nov 07, 2026
Minimum Stay: 4 Days
$532 $3,489 n/a
PMS Rate
Nov 08, 2026 - Nov 08, 2026
Minimum Stay: 4 Days
$511 $3,432 n/a
PMS Rate
Nov 09, 2026 - Nov 10, 2026
Minimum Stay: 4 Days
$475 $3,396 n/a
PMS Rate
Nov 11, 2026 - Nov 11, 2026
Minimum Stay: 4 Days
$483 $3,396 n/a
PMS Rate
Nov 12, 2026 - Nov 12, 2026
Minimum Stay: 4 Days
$538 $3,388 n/a
PMS Rate
Nov 13, 2026 - Nov 14, 2026
Minimum Stay: 4 Days
$475 $3,325 n/a
PMS Rate
Nov 15, 2026 - Nov 15, 2026
Minimum Stay: 4 Days
$475 $3,344 n/a
PMS Rate
Nov 16, 2026 - Nov 16, 2026
Minimum Stay: 4 Days
$475 $3,429 n/a
PMS Rate
Nov 17, 2026 - Nov 17, 2026
Minimum Stay: 4 Days
$475 $3,573 n/a
PMS Rate
Nov 18, 2026 - Nov 18, 2026
Minimum Stay: 4 Days
$475 $3,735 n/a
PMS Rate
Nov 19, 2026 - Nov 19, 2026
Minimum Stay: 4 Days
$475 $4,015 n/a
PMS Rate
Nov 20, 2026 - Nov 20, 2026
Minimum Stay: 4 Days
$475 $4,291 n/a
PMS Rate
Nov 21, 2026 - Nov 21, 2026
Minimum Stay: 4 Days
$494 $4,536 n/a
PMS Rate
Nov 22, 2026 - Nov 22, 2026
Minimum Stay: 4 Days
$560 $4,691 n/a
PMS Rate
Nov 23, 2026 - Nov 23, 2026
Minimum Stay: 4 Days
$619 $4,606 n/a
PMS Rate
Nov 24, 2026 - Nov 24, 2026
Minimum Stay: 4 Days
$637 $4,462 n/a
PMS Rate
Nov 25, 2026 - Nov 25, 2026
Minimum Stay: 4 Days
$755 $4,300 n/a
PMS Rate
Nov 26, 2026 - Nov 26, 2026
Minimum Stay: 4 Days
$751 $4,020 n/a
PMS Rate
Nov 27, 2026 - Nov 27, 2026
Minimum Stay: 4 Days
$720 $3,744 n/a
PMS Rate
Nov 28, 2026 - Nov 28, 2026
Minimum Stay: 4 Days
$649 $3,499 n/a
PMS Rate
Nov 29, 2026 - Dec 12, 2026
Minimum Stay: 4 Days
$475 $3,325 n/a
PMS Rate
Dec 13, 2026 - Dec 13, 2026
Minimum Stay: 4 Days
$475 $3,346 n/a
PMS Rate
Dec 14, 2026 - Dec 14, 2026
Minimum Stay: 4 Days
$475 $3,494 n/a
PMS Rate
Dec 15, 2026 - Dec 15, 2026
Minimum Stay: 4 Days
$475 $3,678 n/a
PMS Rate
Dec 16, 2026 - Dec 16, 2026
Minimum Stay: 4 Days
$475 $3,877 n/a
PMS Rate
Dec 17, 2026 - Dec 17, 2026
Minimum Stay: 4 Days
$475 $4,131 n/a
PMS Rate
Dec 18, 2026 - Dec 18, 2026
Minimum Stay: 4 Days
$475 $4,388 n/a
PMS Rate
Dec 19, 2026 - Dec 19, 2026
Minimum Stay: 4 Days
$496 $4,648 n/a
PMS Rate
Dec 20, 2026 - Dec 20, 2026
Minimum Stay: 4 Days
$623 $4,926 n/a
PMS Rate
Dec 21, 2026 - Dec 21, 2026
Minimum Stay: 4 Days
$659 $5,127 n/a
PMS Rate
Dec 22, 2026 - Dec 22, 2026
Minimum Stay: 4 Days
$674 $5,368 n/a
PMS Rate
Dec 23, 2026 - Dec 23, 2026
Minimum Stay: 4 Days
$729 $5,594 n/a
PMS Rate
Dec 24, 2026 - Dec 24, 2026
Minimum Stay: 4 Days
$732 $5,765 n/a
PMS Rate
Dec 25, 2026 - Dec 25, 2026
Minimum Stay: 4 Days
$735 $5,933 n/a
PMS Rate
Dec 26, 2026 - Dec 26, 2026
Minimum Stay: 4 Days
$774 $6,098 n/a
PMS Rate
Dec 27, 2026 - Dec 27, 2026
Minimum Stay: 4 Days
$824 $6,224 n/a
PMS Rate
Dec 28, 2026 - Dec 28, 2026
Minimum Stay: 4 Days
$900 $5,907 n/a
PMS Rate
Dec 29, 2026 - Dec 29, 2026
Minimum Stay: 4 Days
$900 $5,489 n/a
PMS Rate
Dec 30, 2026 - Dec 30, 2026
Minimum Stay: 4 Days
$900 $5,091 n/a
PMS Rate
Dec 31, 2026 - Dec 31, 2026
Minimum Stay: 4 Days
$900 $4,714 n/a
PMS Rate
Jan 01, 2027 - Jan 01, 2027
Minimum Stay: 4 Days
$900 $4,349 n/a
PMS Rate
Jan 02, 2027 - Jan 02, 2027
Minimum Stay: 4 Days
$900 $3,977 n/a
PMS Rate
Jan 03, 2027 - Jan 03, 2027
Minimum Stay: 4 Days
$507 $3,583 n/a
PMS Rate
Jan 04, 2027 - Jan 04, 2027
Minimum Stay: 4 Days
$482 $3,551 n/a
PMS Rate
Jan 05, 2027 - Jan 05, 2027
Minimum Stay: 4 Days
$502 $3,544 n/a
PMS Rate
Jan 06, 2027 - Jan 06, 2027
Minimum Stay: 4 Days
$523 $3,517 n/a
PMS Rate
Jan 07, 2027 - Jan 07, 2027
Minimum Stay: 4 Days
$535 $3,469 n/a
PMS Rate
Jan 08, 2027 - Jan 08, 2027
Minimum Stay: 4 Days
$528 $3,435 n/a
PMS Rate
Jan 09, 2027 - Jan 09, 2027
Minimum Stay: 4 Days
$506 $3,453 n/a
PMS Rate
Jan 10, 2027 - Jan 10, 2027
Minimum Stay: 4 Days
$475 $3,551 n/a
PMS Rate
Jan 11, 2027 - Jan 11, 2027
Minimum Stay: 4 Days
$475 $3,677 n/a
PMS Rate
Jan 12, 2027 - Jan 12, 2027
Minimum Stay: 4 Days
$475 $3,760 n/a
PMS Rate
Jan 13, 2027 - Jan 13, 2027
Minimum Stay: 4 Days
$475 $3,823 n/a
PMS Rate
Jan 14, 2027 - Jan 14, 2027
Minimum Stay: 4 Days
$501 $3,898 n/a
PMS Rate
Jan 15, 2027 - Jan 15, 2027
Minimum Stay: 4 Days
$546 $3,957 n/a
PMS Rate
Jan 16, 2027 - Jan 16, 2027
Minimum Stay: 4 Days
$604 $3,940 n/a
PMS Rate
Jan 17, 2027 - Jan 17, 2027
Minimum Stay: 4 Days
$601 $3,888 n/a
PMS Rate
Jan 18, 2027 - Jan 18, 2027
Minimum Stay: 4 Days
$558 $3,819 n/a
PMS Rate
Jan 19, 2027 - Jan 19, 2027
Minimum Stay: 4 Days
$538 $3,778 n/a
PMS Rate
Jan 20, 2027 - Jan 20, 2027
Minimum Stay: 4 Days
$550 $3,754 n/a
PMS Rate
Jan 21, 2027 - Jan 21, 2027
Minimum Stay: 4 Days
$560 $3,720 n/a
PMS Rate
Jan 22, 2027 - Jan 22, 2027
Minimum Stay: 4 Days
$529 $3,712 n/a
PMS Rate
Jan 23, 2027 - Jan 23, 2027
Minimum Stay: 4 Days
$552 $3,745 n/a
PMS Rate
Jan 24, 2027 - Jan 24, 2027
Minimum Stay: 4 Days
$532 $3,771 n/a
PMS Rate
Jan 25, 2027 - Jan 25, 2027
Minimum Stay: 4 Days
$517 $3,795 n/a
PMS Rate
Jan 26, 2027 - Jan 26, 2027
Minimum Stay: 4 Days
$514 $3,837 n/a
PMS Rate
Jan 27, 2027 - Jan 27, 2027
Minimum Stay: 4 Days
$516 $3,893 n/a
PMS Rate
Jan 28, 2027 - Jan 28, 2027
Minimum Stay: 4 Days
$552 $3,966 n/a
PMS Rate
Jan 29, 2027 - Jan 29, 2027
Minimum Stay: 4 Days
$562 $4,059 n/a
PMS Rate
Jan 30, 2027 - Jan 30, 2027
Minimum Stay: 4 Days
$578 $4,161 n/a
PMS Rate
Jan 31, 2027 - Jan 31, 2027
Minimum Stay: 4 Days
$556 $4,256 n/a
PMS Rate
Feb 01, 2027 - Feb 01, 2027
Minimum Stay: 4 Days
$559 $4,354 n/a
PMS Rate
Feb 02, 2027 - Feb 02, 2027
Minimum Stay: 4 Days
$570 $4,517 n/a
PMS Rate
Feb 03, 2027 - Feb 03, 2027
Minimum Stay: 4 Days
$589 $4,675 n/a
PMS Rate
Feb 04, 2027 - Feb 04, 2027
Minimum Stay: 4 Days
$645 $4,831 n/a
PMS Rate
Feb 05, 2027 - Feb 05, 2027
Minimum Stay: 4 Days
$664 $4,989 n/a
PMS Rate
Feb 06, 2027 - Feb 06, 2027
Minimum Stay: 4 Days
$673 $5,225 n/a
PMS Rate
Feb 07, 2027 - Feb 07, 2027
Minimum Stay: 4 Days
$654 $5,452 n/a
PMS Rate
Feb 08, 2027 - Feb 08, 2027
Minimum Stay: 4 Days
$722 $5,698 n/a
PMS Rate
Feb 09, 2027 - Feb 09, 2027
Minimum Stay: 4 Days
$728 $5,876 n/a
PMS Rate
Feb 10, 2027 - Feb 10, 2027
Minimum Stay: 4 Days
$745 $6,048 n/a
PMS Rate
Feb 11, 2027 - Feb 11, 2027
Minimum Stay: 4 Days
$803 $6,203 n/a
PMS Rate
Feb 12, 2027 - Feb 15, 2027
Minimum Stay: 4 Days
$900 $6,300 n/a
PMS Rate
Feb 16, 2027 - Feb 21, 2027
Minimum Stay: 4 Days
$900 $6,265 n/a
PMS Rate
Feb 22, 2027 - Feb 22, 2027
Minimum Stay: 4 Days
$865 $6,265 n/a
PMS Rate
Feb 23, 2027 - Apr 04, 2027
Minimum Stay: 4 Days
$900 $6,300 n/a
PMS Rate
Apr 05, 2027 - Apr 06, 2027
Minimum Stay: 4 Days
$900 $6,253 n/a
PMS Rate
Apr 07, 2027 - Apr 10, 2027
Minimum Stay: 4 Days
$900 $6,147 n/a
PMS Rate
Apr 11, 2027 - Apr 11, 2027
Minimum Stay: 4 Days
$853 $6,147 n/a
PMS Rate
Apr 12, 2027 - Apr 12, 2027
Minimum Stay: 4 Days
$900 $6,194 n/a
PMS Rate
Apr 13, 2027 - Apr 13, 2027
Minimum Stay: 4 Days
$794 $6,194 n/a
PMS Rate
Apr 14, 2027 - Apr 17, 2027
Minimum Stay: 4 Days
$900 $6,300 n/a
PMS Rate
Apr 18, 2027 - Apr 18, 2027
Minimum Stay: 4 Days
$900 $6,257 n/a
PMS Rate
Apr 19, 2027 - Apr 19, 2027
Minimum Stay: 4 Days
$900 $6,174 n/a
PMS Rate
Apr 20, 2027 - Apr 20, 2027
Minimum Stay: 4 Days
$900 $6,083 n/a
PMS Rate
Apr 21, 2027 - Apr 21, 2027
Minimum Stay: 4 Days
$900 $5,992 n/a
PMS Rate
Apr 22, 2027 - Apr 22, 2027
Minimum Stay: 4 Days
$900 $5,836 n/a
PMS Rate
Apr 23, 2027 - Apr 23, 2027
Minimum Stay: 4 Days
$900 $5,723 n/a
PMS Rate
Apr 24, 2027 - Apr 24, 2027
Minimum Stay: 4 Days
$857 $5,628 n/a
PMS Rate
Apr 25, 2027 - Apr 25, 2027
Minimum Stay: 4 Days
$817 $5,551 n/a
PMS Rate
Apr 26, 2027 - Apr 26, 2027
Minimum Stay: 4 Days
$809 $5,457 n/a
PMS Rate
Apr 27, 2027 - Apr 27, 2027
Minimum Stay: 4 Days
$809 $5,371 n/a
PMS Rate
Apr 28, 2027 - Apr 28, 2027
Minimum Stay: 4 Days
$744 $5,285 n/a
PMS Rate
Apr 29, 2027 - Apr 29, 2027
Minimum Stay: 4 Days
$787 $5,217 n/a
PMS Rate
Apr 30, 2027 - Apr 30, 2027
Minimum Stay: 4 Days
$805 $5,163 n/a
PMS Rate
May 01, 2027 - May 01, 2027
Minimum Stay: 4 Days
$780 $5,156 n/a
PMS Rate
May 02, 2027 - May 02, 2027
Minimum Stay: 4 Days
$723 $5,147 n/a
PMS Rate
May 03, 2027 - May 03, 2027
Minimum Stay: 4 Days
$723 $5,116 n/a
PMS Rate
May 04, 2027 - May 04, 2027
Minimum Stay: 4 Days
$723 $5,030 n/a
PMS Rate
May 05, 2027 - May 05, 2027
Minimum Stay: 4 Days
$676 $4,952 n/a
PMS Rate
May 06, 2027 - May 06, 2027
Minimum Stay: 4 Days
$733 $4,965 n/a
PMS Rate
May 07, 2027 - May 07, 2027
Minimum Stay: 4 Days
$798 $4,999 n/a
PMS Rate
May 08, 2027 - May 08, 2027
Minimum Stay: 4 Days
$771 $4,999 n/a
PMS Rate
May 09, 2027 - May 09, 2027
Minimum Stay: 4 Days
$692 $5,056 n/a
PMS Rate
May 10, 2027 - May 10, 2027
Minimum Stay: 4 Days
$637 $5,161 n/a
PMS Rate
May 11, 2027 - May 11, 2027
Minimum Stay: 4 Days
$645 $5,321 n/a
PMS Rate
May 12, 2027 - May 12, 2027
Minimum Stay: 4 Days
$689 $5,380 n/a
PMS Rate
May 13, 2027 - May 13, 2027
Minimum Stay: 4 Days
$767 $5,435 n/a
PMS Rate
May 14, 2027 - May 14, 2027
Minimum Stay: 4 Days
$798 $5,474 n/a
PMS Rate
May 15, 2027 - May 15, 2027
Minimum Stay: 4 Days
$828 $5,534 n/a
PMS Rate
May 16, 2027 - May 16, 2027
Minimum Stay: 4 Days
$797 $5,594 n/a
PMS Rate
May 17, 2027 - May 17, 2027
Minimum Stay: 4 Days
$797 $5,627 n/a
PMS Rate
May 18, 2027 - May 18, 2027
Minimum Stay: 4 Days
$704 $5,658 n/a
PMS Rate
May 19, 2027 - May 19, 2027
Minimum Stay: 4 Days
$744 $5,829 n/a
PMS Rate
May 20, 2027 - May 20, 2027
Minimum Stay: 4 Days
$806 $5,937 n/a
PMS Rate
May 21, 2027 - May 21, 2027
Minimum Stay: 4 Days
$858 $6,031 n/a
PMS Rate
May 22, 2027 - May 22, 2027
Minimum Stay: 4 Days
$888 $6,073 n/a
PMS Rate
May 23, 2027 - May 23, 2027
Minimum Stay: 4 Days
$830 $6,085 n/a
PMS Rate
May 24, 2027 - May 24, 2027
Minimum Stay: 4 Days
$828 $6,155 n/a
PMS Rate
May 25, 2027 - May 25, 2027
Minimum Stay: 4 Days
$875 $6,227 n/a
PMS Rate
May 26, 2027 - May 26, 2027
Minimum Stay: 4 Days
$852 $6,252 n/a
PMS Rate
May 27, 2027 - Jul 31, 2027
Minimum Stay: 4 Days
$900 $6,300 n/a
PMS Rate
Aug 01, 2027 - Aug 01, 2027
Minimum Stay: 4 Days
$900 $6,222 n/a
PMS Rate
Aug 02, 2027 - Aug 02, 2027
Minimum Stay: 4 Days
$900 $6,128 n/a
PMS Rate
Aug 03, 2027 - Aug 03, 2027
Minimum Stay: 4 Days
$900 $5,971 n/a
PMS Rate
Aug 04, 2027 - Aug 04, 2027
Minimum Stay: 4 Days
$900 $5,793 n/a
PMS Rate
Aug 05, 2027 - Aug 05, 2027
Minimum Stay: 4 Days
$900 $5,652 n/a
PMS Rate
Aug 06, 2027 - Aug 06, 2027
Minimum Stay: 4 Days
$900 $5,549 n/a
PMS Rate
Aug 07, 2027 - Aug 07, 2027
Minimum Stay: 4 Days
$822 $5,426 n/a
PMS Rate
Aug 08, 2027 - Aug 08, 2027
Minimum Stay: 4 Days
$806 $5,266 n/a
PMS Rate
Aug 09, 2027 - Aug 09, 2027
Minimum Stay: 4 Days
$743 $5,140 n/a
PMS Rate
Aug 10, 2027 - Aug 10, 2027
Minimum Stay: 4 Days
$722 $5,077 n/a
PMS Rate
Aug 11, 2027 - Aug 11, 2027
Minimum Stay: 4 Days
$759 $5,035 n/a
PMS Rate
Aug 12, 2027 - Aug 12, 2027
Minimum Stay: 4 Days
$797 $4,956 n/a
PMS Rate
Aug 13, 2027 - Aug 13, 2027
Minimum Stay: 4 Days
$777 $4,805 n/a
PMS Rate
Aug 14, 2027 - Aug 14, 2027
Minimum Stay: 4 Days
$662 $4,699 n/a
PMS Rate
Aug 15, 2027 - Aug 15, 2027
Minimum Stay: 4 Days
$680 $4,652 n/a
PMS Rate
Aug 16, 2027 - Aug 16, 2027
Minimum Stay: 4 Days
$680 $4,532 n/a
PMS Rate
Aug 17, 2027 - Aug 17, 2027
Minimum Stay: 4 Days
$680 $4,370 n/a
PMS Rate
Aug 18, 2027 - Aug 18, 2027
Minimum Stay: 4 Days
$680 $4,217 n/a
PMS Rate
Aug 19, 2027 - Aug 19, 2027
Minimum Stay: 4 Days
$646 $4,073 n/a
PMS Rate
Aug 20, 2027 - Aug 20, 2027
Minimum Stay: 4 Days
$671 $4,038 n/a
PMS Rate
Aug 21, 2027 - Aug 21, 2027
Minimum Stay: 4 Days
$615 $4,041 n/a
PMS Rate
Aug 22, 2027 - Aug 22, 2027
Minimum Stay: 4 Days
$560 $4,049 n/a
PMS Rate
Aug 23, 2027 - Aug 23, 2027
Minimum Stay: 4 Days
$518 $4,100 n/a
PMS Rate
Aug 24, 2027 - Aug 24, 2027
Minimum Stay: 4 Days
$527 $4,111 n/a
PMS Rate
Aug 25, 2027 - Aug 25, 2027
Minimum Stay: 4 Days
$536 $4,108 n/a
PMS Rate
Aug 26, 2027 - Aug 26, 2027
Minimum Stay: 4 Days
$611 $4,153 n/a
PMS Rate
Aug 27, 2027 - Aug 27, 2027
Minimum Stay: 4 Days
$674 $4,142 n/a
PMS Rate
Aug 28, 2027 - Aug 28, 2027
Minimum Stay: 4 Days
$623 $4,368 n/a
PMS Rate
Aug 29, 2027 - Aug 29, 2027
Minimum Stay: 4 Days
$611 $4,637 n/a
PMS Rate
Aug 30, 2027 - Aug 30, 2027
Minimum Stay: 4 Days
$529 $4,920 n/a
PMS Rate
Aug 31, 2027 - Aug 31, 2027
Minimum Stay: 4 Days
$524 $4,909 n/a
PMS Rate
Sep 01, 2027 - Sep 01, 2027
Minimum Stay: 4 Days
$581 $4,886 n/a
PMS Rate
Sep 02, 2027 - Sep 02, 2027
Minimum Stay: 4 Days
$600 $4,826 n/a
PMS Rate
Sep 03, 2027 - Sep 03, 2027
Minimum Stay: 4 Days
$900 $4,777 n/a
PMS Rate
Sep 04, 2027 - Sep 04, 2027
Minimum Stay: 4 Days
$892 $4,464 n/a
PMS Rate
Sep 05, 2027 - Sep 05, 2027
Minimum Stay: 4 Days
$894 $4,158 n/a
PMS Rate
Sep 06, 2027 - Sep 06, 2027
Minimum Stay: 4 Days
$518 $3,812 n/a
PMS Rate
Sep 07, 2027 - Sep 07, 2027
Minimum Stay: 4 Days
$501 $3,811 n/a
PMS Rate
Sep 08, 2027 - Sep 08, 2027
Minimum Stay: 4 Days
$521 $3,818 n/a
PMS Rate
Sep 09, 2027 - Sep 09, 2027
Minimum Stay: 4 Days
$551 $3,829 n/a
PMS Rate
Sep 10, 2027 - Sep 10, 2027
Minimum Stay: 4 Days
$587 $3,845 n/a
PMS Rate
Sep 11, 2027 - Sep 11, 2027
Minimum Stay: 4 Days
$586 $3,878 n/a
PMS Rate
Sep 12, 2027 - Sep 12, 2027
Minimum Stay: 4 Days
$548 $3,891 n/a
PMS Rate
Sep 13, 2027 - Sep 13, 2027
Minimum Stay: 4 Days
$517 $3,902 n/a
PMS Rate
Sep 14, 2027 - Sep 14, 2027
Minimum Stay: 4 Days
$508 $3,937 n/a
PMS Rate
Sep 15, 2027 - Sep 15, 2027
Minimum Stay: 4 Days
$532 $3,989 n/a
PMS Rate
Sep 16, 2027 - Sep 16, 2027
Minimum Stay: 4 Days
$567 $4,020 n/a
PMS Rate
Sep 17, 2027 - Sep 17, 2027
Minimum Stay: 4 Days
$620 $4,032 n/a
PMS Rate
Sep 18, 2027 - Sep 18, 2027
Minimum Stay: 4 Days
$599 $4,021 n/a
PMS Rate
Sep 19, 2027 - Sep 19, 2027
Minimum Stay: 4 Days
$559 $4,027 n/a
PMS Rate
Sep 20, 2027 - Sep 20, 2027
Minimum Stay: 4 Days
$552 $4,031 n/a
PMS Rate
Sep 21, 2027 - Sep 21, 2027
Minimum Stay: 4 Days
$560 $3,991 n/a
PMS Rate
Sep 22, 2027 - Sep 22, 2027
Minimum Stay: 4 Days
$563 $3,931 n/a
PMS Rate
Sep 23, 2027 - Sep 23, 2027
Minimum Stay: 4 Days
$579 $3,895 n/a
PMS Rate
Sep 24, 2027 - Sep 24, 2027
Minimum Stay: 4 Days
$609 $3,897 n/a
PMS Rate
Sep 25, 2027 - Sep 25, 2027
Minimum Stay: 4 Days
$605 $3,893 n/a
PMS Rate
Sep 26, 2027 - Sep 26, 2027
Minimum Stay: 4 Days
$563 $3,897 n/a
PMS Rate
Sep 27, 2027 - Sep 27, 2027
Minimum Stay: 4 Days
$512 $3,904 n/a
PMS Rate
Sep 28, 2027 - Sep 28, 2027
Minimum Stay: 4 Days
$500 $3,984 n/a
PMS Rate
Sep 29, 2027 - Sep 29, 2027
Minimum Stay: 4 Days
$527 $4,080 n/a
PMS Rate
Sep 30, 2027 - Sep 30, 2027
Minimum Stay: 4 Days
$581 $4,150 n/a
PMS Rate
Oct 01, 2027 - Oct 01, 2027
Minimum Stay: 4 Days
$605 $4,210 n/a
PMS Rate
Oct 02, 2027 - Oct 02, 2027
Minimum Stay: 4 Days
$609 $4,332 n/a
PMS Rate
Oct 03, 2027 - Oct 03, 2027
Minimum Stay: 4 Days
$570 $4,445 n/a
PMS Rate
Oct 04, 2027 - Oct 04, 2027
Minimum Stay: 4 Days
$592 $4,602 n/a
PMS Rate
Oct 05, 2027 - Oct 05, 2027
Minimum Stay: 4 Days
$596 $4,626 n/a
PMS Rate
Oct 06, 2027 - Oct 06, 2027
Minimum Stay: 4 Days
$597 $4,646 n/a
PMS Rate
Oct 07, 2027 - Oct 07, 2027
Minimum Stay: 4 Days
$641 $4,693 n/a
PMS Rate
Oct 08, 2027 - Oct 08, 2027
Minimum Stay: 4 Days
$727 $4,732 n/a
PMS Rate
Oct 09, 2027 - Oct 09, 2027
Minimum Stay: 4 Days
$722 $4,709 n/a
PMS Rate
Oct 10, 2027 - Oct 10, 2027
Minimum Stay: 4 Days
$727 $4,678 n/a
PMS Rate
Oct 11, 2027 - Oct 11, 2027
Minimum Stay: 4 Days
$616 $4,574 n/a
PMS Rate
Oct 12, 2027 - Oct 12, 2027
Minimum Stay: 4 Days
$616 $4,548 n/a
PMS Rate
Oct 13, 2027 - Oct 13, 2027
Minimum Stay: 4 Days
$644 $4,518 n/a
PMS Rate
Oct 14, 2027 - Oct 14, 2027
Minimum Stay: 4 Days
$680 $4,462 n/a
PMS Rate
Oct 15, 2027 - Oct 15, 2027
Minimum Stay: 4 Days
$704 $4,389 n/a
PMS Rate
Oct 16, 2027 - Oct 16, 2027
Minimum Stay: 4 Days
$691 $4,310 n/a
PMS Rate
Oct 17, 2027 - Oct 17, 2027
Minimum Stay: 4 Days
$623 $4,228 n/a
PMS Rate
Oct 18, 2027 - Oct 18, 2027
Minimum Stay: 4 Days
$590 $4,254 n/a
PMS Rate
Oct 19, 2027 - Oct 19, 2027
Minimum Stay: 4 Days
$586 $4,313 n/a
PMS Rate
Oct 20, 2027 - Oct 20, 2027
Minimum Stay: 4 Days
$588 $4,376 n/a
PMS Rate
Oct 21, 2027 - Oct 21, 2027
Minimum Stay: 4 Days
$607 $4,437 n/a
PMS Rate
Oct 22, 2027 - Oct 22, 2027
Minimum Stay: 4 Days
$625 $4,479 n/a
About this rental

About This Rental

Pineapple Cottage is a ground-level 4-bedroom, 3-bath home in Anna Maria that accommodates up to 8 guests. The setting is listed as waterfront-nearby and near a beach, with beach distance noted at 0.3 miles. The home has been restored following hurricanes Helene and Milton and offers keyless entry via a keypad.

Sleeping arrangements include a king bed in the primary bedroom, a second king bedroom, a queen bedroom, and a trundle bed in the fourth bedroom. Core in-home amenities include air conditioning, ceiling fans, internet access, televisions, towels/linens, and a washer/dryer. Safety items noted include a fire extinguisher and smoke detector, and a Ring door camera is installed at the front entrance.

For meals and downtime at the house, the kitchen includes a refrigerator, freezer, microwave, dishwasher, coffee maker, and blender. Outdoor features include a private pool and hot tub/spa, plus a patio and grill. Pool heating is seasonal (approximately Thanksgiving to Easter) and temperature limits are specified; spa temperature defaults to pool temperature when not in use.

Additional stay details include a starter supply kit (paper goods, trash bags, laundry detergent, and coffee/tea) and provided bath and bed linens. Dogs 25 lbs or less are allowed with a separate pet fee per pet. The garage is reserved for owner storage with no guest access. House rules also note a 4-night minimum stay, age requirements for guests under 25, and that the home is not intended for parties or large gatherings.

Welcome to “Pineapple Cottage” – a beautifully updated ground-level beach cottage located in the heart of Anna Maria City and just 1 block from all the shops, restaurants, and fun on Pine Avenue. This charming cottage has been completely restored after hurricanes Helene and Milton. This property is better than ever and offers all the luxuries you will come to expect from Staying with Salty Mermaid Vacation Rentals. Leave your car parked (3 spots provided) – the town is very walkable and this property offers an excellent location in the center of it all, plus our island’s free trolley is only a few flip flop steps away on Pine Ave. Pineapple Cottage offers 4 bedrooms, 3 baths and was professionally designed to create a warm and inviting atmosphere. Take a swim in your private tropical oasis – where the saltwater pool and spa are heated or light the gas grill for a barbecue with friends and spend your evening relaxing on the back porch. Your family will enjoy get-togethers with all the outdoor shaded private space. As always, we make sure you have the ability to stay connected on our free high-speed wireless internet! Kick back relax turn on the Flat screen and catch that flick you always wanted to see or that must-see sports game.

Disclaimers:

*Florida Law requires an audible alarm to be installed on doors and windows that open to a pool area. The purpose of these alarms is to alert an adult if a child walks out to a pool area unattended. These alarms typically have a bypass button that allows the door to be opened for 7 seconds before the alarm goes off. These alarms must not be removed or tampered with in any way. Any evidence of tampering or damage to pool alarms will be billed to the credit card on file for the reservation.*

*Dogs 25lbs or Less are welcome, A $ 250+ tax pet fee is required per pet, This is a separate fee paid directly to Salty Mermaid Real Estate after booking. Pets that are not disclosed to our office will result in additional cleaning charges to your reservation.

*Check-in time is 4 pm on the day of your arrival, Check out time is 10 am on the day of your departure. No early access or late departure is allowed unless special arrangements are made with our office, Our cleaning and Inspection team need time to ensure the rental is clean and safe for your stay*

*A starter kit of paper towels, toilet paper, trash bags, laundry detergent, and coffee & tea. Full sized luxury hand soap, shampoo, conditioner, and body wash are provided at check-in. Also available if requested, while supplies last, is a toothbrush and sewing kit. Any additional items that you may need during your stay can be purchased at one of the local grocery stores.*

*White Duvet covers and inserts, white bed linens, multi color beach towels, white bath towels, white wash clothes, white bathroom floor towels, black makeup towels, kitchen towels, premium pillows, vacuum sealed throw blankets* 

*Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!*

*This home has a 4-night minimum stay requirement*

*Reservations that are 30 nights or longer will require a mid-stay clean, one of our rental agents will provide more information at the time of booking.

*The Bikes in the Photos are not included with the rental, if you would like more info on bike rental options please reach out to us and we will be happy to help*

*The Garage is the Owners personal storage space, no guest access allowed*

*Ring Door camera at front Entrance*

*Please note this is not a party or large gathering house. Noise complaints will result in eviction*

*Parking for 2 Vehicles side by side on the driveway, do not block sidewalk, you can park in the grass strip in front of the house too, do not have any tires on the street, you will get a ticket.

*Pools are heated from approximately Thanksgiving to Easter only and are set no higher than 80 degrees. Spa temperatures default to the pool temperature when not in use and can reach 100 Degrees under normal weather circumstances. During colder weather, we cannot guarantee that the pool/spa can be maintained to that degree. No refunds, credits, or discounts will be offered if the pool/spa temperature cannot be maintained due to unusually cold weather*
Things to enjoy

Activities and Special Interests

This property provides access to the following activities and special interests:

Beach
Biking
Boating
Canoeing
Fishing
Deep Sea Fishing
Golfing
State National Parks
Ocean
Pet Friendly
Sailing
Scuba Diving
Surfing
Fly Fishing
Wind Surfing
Family Vacations
Kayaking
What's included

Property Amenities

Featured Amenities

Air Conditioning
Dishwasher
Grill
Hot Tub
Internet Access
Pool (Private)
Television
Washer/Dryer

Property Features

Blender
Ceiling Fan(s)
Coffee Maker
Freezer
Hair Dryer
Microwave
Parking
Refrigerator
Towels/Linens

Other Property Amenities

Beach Distance: 0.3 Mi
Bed Size 1st/Master: King
Bed Size 2nd Rm: King
Bed Size 3rd Rm: Queen
Bed Size 4th Rm: Trundle
Patio
TVs/VCR/DVD
Key Pad
Iron
Fire Extinguisher
Smoke Detector
Helpful details

Frequently Asked Questions

Pineapple Cottage is located in Anna Maria, Florida.

Pineapple Cottage accommodates up to 8 guests.

4 Bedrooms and 3 Full Bathrooms.

The listed beach access for Pineapple Cottage is Near a Beach.

Yes. The property lists Pool (Private).

Yes. Pineapple Cottage is listed as pet friendly. Review the manager's policies for any pet restrictions or fees.
Local management

Professionally Managed By

Salty Mermaid Real Estate & Vacation Rentals
In business since 2018
View Manager Profile

Questions about this rental?

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Property reference
#181639 · Pineapple Cottage
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