How many guests can the property accommodate?

This property accommodates a maximum of 6 guests.

Yes, pets are welcome. Up to 2 pets

This is a non-smoking property.

What is the minimum stay?

The minimum stay at this property is 5 nights.

Is there a cleaning fee?

Yes, a cleaning fee of $350 applies.

Carefree Cay

Availability

Next 90 nights, as of Nov 8, 2026: unavailable Nov 8 to Dec 11, Dec 19 to Jan 29 and Jan 31 to Feb 5; otherwise open from $245 a night, 4-night minimum.

A date marked available means check-in is allowed that night. A stay is bookable when the check-in night is available, the stay meets the minimum, and no night in between is unavailable. Rates are per night before taxes, cleaning and other fees; the Agent Checkout gives the dated total.

Date	Nightly rate	Availability	Minimum stay
Nov 8, 2026	—	Not available	4
Nov 9, 2026	—	Not available	4
Nov 10, 2026	—	Not available	4
Nov 11, 2026	—	Not available	4
Nov 12, 2026	—	Not available	4
Nov 13, 2026	—	Not available	4
Nov 14, 2026	—	Not available	4
Nov 15, 2026	—	Not available	4
Nov 16, 2026	—	Not available	4
Nov 17, 2026	—	Not available	4
Nov 18, 2026	—	Not available	4
Nov 19, 2026	—	Not available	4
Nov 20, 2026	—	Not available	4
Nov 21, 2026	—	Not available	7
Nov 22, 2026	—	Not available	7
Nov 23, 2026	—	Not available	7
Nov 24, 2026	—	Not available	7
Nov 25, 2026	—	Not available	7
Nov 26, 2026	—	Not available	7
Nov 27, 2026	—	Not available	7
Nov 28, 2026	—	Not available	4
Nov 29, 2026	—	Not available	4
Nov 30, 2026	—	Not available	4
Dec 1, 2026	—	Not available	4
Dec 2, 2026	—	Not available	4
Dec 3, 2026	—	Not available	4
Dec 4, 2026	—	Not available	4
Dec 5, 2026	—	Not available	4
Dec 6, 2026	—	Not available	4
Dec 7, 2026	—	Not available	4
Dec 8, 2026	—	Not available	4
Dec 9, 2026	—	Not available	4
Dec 10, 2026	—	Not available	4
Dec 11, 2026	—	Not available	5
Dec 12, 2026	$295	Available	5
Dec 13, 2026	$250	Available	5
Dec 14, 2026	$245	Available	5
Dec 15, 2026	$245	Available	5
Dec 16, 2026	$245	Available	5
Dec 17, 2026	$261	Available	5
Dec 18, 2026	$284	Available	5
Dec 19, 2026	—	Not available	7
Dec 20, 2026	—	Not available	7
Dec 21, 2026	—	Not available	7
Dec 22, 2026	—	Not available	7
Dec 23, 2026	—	Not available	7
Dec 24, 2026	—	Not available	7
Dec 25, 2026	—	Not available	7
Dec 26, 2026	—	Not available	7
Dec 27, 2026	—	Not available	7
Dec 28, 2026	—	Not available	7
Dec 29, 2026	—	Not available	7
Dec 30, 2026	—	Not available	7
Dec 31, 2026	—	Not available	7
Jan 1, 2027	—	Not available	7
Jan 2, 2027	—	Not available	5
Jan 3, 2027	—	Not available	5
Jan 4, 2027	—	Not available	5
Jan 5, 2027	—	Not available	5
Jan 6, 2027	—	Not available	5
Jan 7, 2027	—	Not available	5
Jan 8, 2027	—	Not available	5
Jan 9, 2027	—	Not available	5
Jan 10, 2027	—	Not available	5
Jan 11, 2027	—	Not available	5
Jan 12, 2027	—	Not available	5
Jan 13, 2027	—	Not available	5
Jan 14, 2027	—	Not available	5
Jan 15, 2027	—	Not available	5
Jan 16, 2027	—	Not available	5
Jan 17, 2027	—	Not available	5
Jan 18, 2027	—	Not available	5
Jan 19, 2027	—	Not available	5
Jan 20, 2027	—	Not available	5
Jan 21, 2027	—	Not available	5
Jan 22, 2027	—	Not available	5
Jan 23, 2027	—	Not available	5
Jan 24, 2027	—	Not available	5
Jan 25, 2027	—	Not available	5
Jan 26, 2027	—	Not available	5
Jan 27, 2027	—	Not available	5
Jan 28, 2027	—	Not available	5
Jan 29, 2027	—	Not available	5
Jan 30, 2027	$503	Available	4
Jan 31, 2027	—	Not available	5
Feb 1, 2027	—	Not available	5
Feb 2, 2027	—	Not available	5
Feb 3, 2027	—	Not available	5
Feb 4, 2027	—	Not available	5
Feb 5, 2027	—	Not available	5
Feb 6, 2027	—	Not available	5
Feb 7, 2027	—	Not available	5
Feb 8, 2027	—	Not available	5
Feb 9, 2027	—	Not available	5
Feb 10, 2027	—	Not available	5
Feb 11, 2027	—	Not available	5
Feb 12, 2027	—	Not available	5
Feb 13, 2027	—	Not available	7
Feb 14, 2027	—	Not available	7
Feb 15, 2027	—	Not available	7
Feb 16, 2027	—	Not available	7
Feb 17, 2027	—	Not available	7
Feb 18, 2027	—	Not available	7
Feb 19, 2027	—	Not available	7
Feb 20, 2027	—	Not available	7
Feb 21, 2027	—	Not available	7
Feb 22, 2027	—	Not available	7
Feb 23, 2027	—	Not available	7
Feb 24, 2027	—	Not available	7
Feb 25, 2027	—	Not available	7
Feb 26, 2027	—	Not available	7
Feb 27, 2027	—	Not available	7
Feb 28, 2027	—	Not available	7
Mar 1, 2027	—	Not available	7
Mar 2, 2027	—	Not available	7
Mar 3, 2027	—	Not available	7
Mar 4, 2027	—	Not available	7
Mar 5, 2027	—	Not available	7
Mar 6, 2027	—	Not available	7
Mar 7, 2027	—	Not available	7
Mar 8, 2027	—	Not available	7
Mar 9, 2027	—	Not available	7
Mar 10, 2027	—	Not available	7
Mar 11, 2027	—	Not available	7
Mar 12, 2027	—	Not available	7
Mar 13, 2027	—	Not available	7
Mar 14, 2027	—	Not available	7
Mar 15, 2027	—	Not available	7
Mar 16, 2027	—	Not available	7
Mar 17, 2027	—	Not available	7
Mar 18, 2027	—	Not available	7
Mar 19, 2027	—	Not available	7
Mar 20, 2027	—	Not available	7
Mar 21, 2027	—	Not available	7
Mar 22, 2027	—	Not available	7
Mar 23, 2027	—	Not available	7
Mar 24, 2027	—	Not available	7
Mar 25, 2027	—	Not available	7
Mar 26, 2027	—	Not available	7
Mar 27, 2027	$1295	Available	7
Mar 28, 2027	$1272	Available	7
Mar 29, 2027	$1261	Available	7
Mar 30, 2027	$1233	Available	7
Mar 31, 2027	$1185	Available	7
Apr 1, 2027	$1184	Available	7
Apr 2, 2027	$1172	Available	7
Apr 3, 2027	$1023	Available	5
Apr 4, 2027	$961	Available	5
Apr 5, 2027	$1031	Available	5
Apr 6, 2027	$889	Available	5
Apr 7, 2027	$924	Available	5
Apr 8, 2027	$886	Available	5
Apr 9, 2027	$843	Available	5
Apr 10, 2027	$787	Available	5
Apr 11, 2027	$751	Available	5
Apr 12, 2027	$710	Available	5
Apr 13, 2027	$676	Available	5
Apr 14, 2027	$772	Available	5
Apr 15, 2027	$780	Available	5
Apr 16, 2027	$785	Available	5
Apr 17, 2027	$793	Available	5
Apr 18, 2027	$819	Available	5
Apr 19, 2027	$819	Available	5
Apr 20, 2027	$819	Available	5
Apr 21, 2027	$819	Available	5
Apr 22, 2027	$819	Available	5
Apr 23, 2027	$819	Available	5
Apr 24, 2027	$860	Available	5
Apr 25, 2027	$753	Available	5
Apr 26, 2027	$753	Available	5
Apr 27, 2027	$753	Available	5
Apr 28, 2027	$753	Available	5
Apr 29, 2027	$753	Available	5
Apr 30, 2027	$822	Available	5
May 1, 2027	$744	Available	5
May 2, 2027	$716	Available	5
May 3, 2027	$695	Available	5
May 4, 2027	$684	Available	5
May 5, 2027	$779	Available	5
May 6, 2027	$715	Available	5

186 more nights on the full rate calendar.

Your carefree Anna Maria Island escape with a private pool, spa, and game room, just steps from the beach.

Carefree Cay is located on a quiet residential street on the north end of Anna Maria Island with an immaculate backyard with a pool and in-ground spa!

Amenities (101)

Kitchen: Coffee Maker, Dishes and Utensils, Dishwasher, Microwave, Oven, Refrigerator, Stove, Pots and Pans, Toaster, Kitchen Island, Dining Table, Keurig Coffee Maker, Blender, Wine Glasses, Baking Sheet, BBQ Utensils, Freezer, Hot Water Kettle, Ice Maker
Parking: Three (3) Parking Spaces
Exterior: Backyard, Balcony, BBQ Grill, Heated Pool, Hot Tub or Spa, Private Pool, Fenced Yard, Deck, Outdoor Seating, Outdoor Shower, Outdoor TV, Outdoor Dining Area, Sun Loungers, Uncovered Deck
Interior: Living Room, Full Kitchen, Dedicated Workspace, Bathtub, Clothing Storage, Ceiling Fans, Desk
Essentials: Bed Linens, Towels, Hair Dryer, Clothes Hangers, Hot Water, Long Term Stays Allowed, Private Entrance, Hospital Close By, Wifi, Air Conditioning, Heating, Beach Towels Included, Free Wifi, Pack 'n Play, Dryer, Iron and Ironing Board, Washer, Beach Chairs Provided, Pets Allowed, Required Stairs
Home Safety: Fire Extinguisher, Smoke Detector, Carbon Monoxide Detector, Deadbolt Lock, Contactless Check-In, Keyless Lock, Outdoor Lighting
Things to Do Nearby: Museums, Boating, Local Eco Tourism, Horseback Riding, Outlet Shopping, Wildlife Viewing, Fitness Center, Laundromat, Tennis Court, Basketball Court, Fishing, Hiking, Jet Skiing, Parasailing, Sailing, Snorkeling, Surfing, Swimming, Water Sports, Golf, Health Beauty Spa, Marina, Shopping, Bird Watching, Kayaking
Fun and Entertainment: TV, TV with Cable, Pool Table, Smart TV, Board Games, Games, Books and Reading Material, Game Room

Carefree Cay

Availability

Amenities (101)

Photos (52)

For AI agents