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Family-friendly vacation rentals in Anna Maria

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Anna Maria

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.
Home in Anna Maria
4.95 out of 5 average rating, 195 reviews

Limited Availably w/ Private Boat Dock & 30' Pool

✨ 4.95★ GUEST FAVORITE! Canal Front & 1/2 Block to Beach Experience the ultimate AMI getaway! This 4.95-star tropical oasis features a wide canal with a 30' boat/fishing dock, a massive 16'x30' private pool, and is just a 1/2 block to the beach. Walk to everything:• 3-min walk to Bay Beach, 15 to Bean Point• Steps to Pine Ave shopping & City Pier• Stroll to Waterfront Restaurant & Two Scoops. Bring your boat, lounge poolside, or hit the sand. Perfect island living with 200+ rave reviews!

Top guest favorite
Home in Holmes Beach
5 out of 5 average rating, 13 reviews

Beautiful Beach house! Heated pool and spa!

Discover your dream getaway at this beautifully decorated vacation rental in Anna Maria Island. This stunning 4-bedroom, 4.5-bathroom home offers luxury and comfort, featuring a spacious open-concept living area, modern kitchen, and elegant furnishings. Enjoy the private pool and hot tub, and the beach is just a 5-minute walk away. The highlight is the rooftop deck, where you can soak in breathtaking sunsets. Experience the perfect blend of style and convenience for your unforgettable vacation!

Top guest favorite
Townhouse in Anna Maria
4.93 out of 5 average rating, 130 reviews

Green Jacaranda /Bean Point Beach 5 min walk/pool

Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

Top guest favorite
A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.
Home in Holmes Beach
4.96 out of 5 average rating, 207 reviews

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

Superhost
Home in Holmes Beach
5 out of 5 average rating, 4 reviews

Payton's Place | Private Heated Saltwater Pool/Spa

Slow down, settle in, and soak up the island pace of life. Your family will be close to everything when you stay at this centrally located private home — just a short stroll to local restaurants, charming shops, and the free trolley stop at the end of the street by the library. The white sand beaches and turquoise Gulf waters are only a 7-minute walk away. Spend your mornings at the beach, your afternoons by the heated saltwater pool, and your evenings under the stars in your private spa.

Top guest favorite
Home in Anna Maria
5 out of 5 average rating, 24 reviews

Manatee Sanctuary - in the heart of Anna Maria

Welcome to Manatee Sanctuary – a spacious 3 bed/ 2 bath canal-front retreat with a private heated pool and hot tub, located in the quiet and highly sought-after North End of the island. This serene and private oasis offers everything you need for a relaxed and memorable beach vacation. The home features an open-concept living and dining area, fully stocked kitchen, and an upstairs porch ideal for morning coffee or evening relaxation. The backyard opens onto a peaceful saltwater canal.

Guest favorite
Home in Holmes Beach
4.94 out of 5 average rating, 17 reviews

Heated Pool, Hot Tub, Game Room, Steps to Beach!

Welcome to Island Dreams, the ultimate peaceful escape just 4 min walk from Anna Maria Island's stunning beaches. This fully renovated three-bedroom, three-bath beach house features a Zen-inspired backyard oasis, a private cocktail pool, and a game room! Walk to shops, restaurants, and the trolley stop! Island Dreams offers the perfect blend of relaxation, location, and indoor and outdoor fun! NOTE: Holmes Beach has a 7-day rental minimum. Check in / Check out days are on Saturdays.

Top guest favorite
A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.
Home in Holmes Beach
4.97 out of 5 average rating, 105 reviews

Salty Harbor AMI pool retreat near the Beach

Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our calendar! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

Top guest favorite
A private pool is surrounded by tropical landscaping, featuring a clear blue water surface that reflects soft lighting. Several lounge chairs are positioned nearby, providing relaxation space under the palm trees. The serene area is perfect for unwinding after a day at the beach.
Home in Anna Maria
4.96 out of 5 average rating, 100 reviews

Beach House w/Private Pool & Spa

Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the beautiful beach is right by the house. This 3 bedroom 2 bathroom home is situated on a corner lot on a quiet street and is located just steps to the beaches of the Gulf of Mexico. Enjoy the private pool and spa, surrounded by tropical landscaping. Tons of beach gear included! It is located in a great area to explore by bike, ride to Pine Ave., Bayfront Park, the City Pier, etc....

Top guest favorite
The outdoor area features a spacious pool and a separate spa, surrounded by manicured gardens and palm trees. A covered lanai with steps leads to the upper level of the home, which includes expansive sliding glass doors inviting natural light into the interior.
Home in Anna Maria
4.97 out of 5 average rating, 35 reviews

Ocean Air Oasis-New Centrally Located AMI Luxury

Immerse yourself in coastal luxury at this exceptional 3-bedroom, 2.5-bathroom custom home, where opulent high-end finishes and stunning pecky cypress floors adorn every nook. Revel in the impeccable features, including Sub-Zero and Wolf appliances, marble countertops, Shaw’s sinks, and exquisite custom woodworking, all bathed in abundant natural light. This delightful space offers panoramic views of the lavish backyard, complete with a heated pool and spa.

Guest favorite
A vast shared swimming pool area is surrounded by a sun-drenched patio. Several lounge chairs are positioned along the edge, while a jacuzzi is located at one end of the pool, all framed by lush tropical greenery.
Home in Holmes Beach
4.92 out of 5 average rating, 76 reviews

Home with heated pool, spa, games, walk to beach

Escape to this modern 2BR/2BA beachside retreat on Anna Maria Island. Enjoy a sunlit open-concept living area with coastal décor and a fully equipped kitchen with stainless appliances. After a day in the sun, relax in two tranquil bedrooms, including a master suite. A dedicated workspace keeps you connected, and families will love the convenience of an in-unit washer and dryer plus a high chair for little ones. Rental Certificate: VRC22-000002

Superhost
Home in Anna Maria

Paradise on Pine

Welcome to "Paradise on Pine" – a stylish island retreat perfectly situated in the heart of Anna Maria! This charming 3-bedroom, 2-bath vacation home is nestled right on Pine Avenue – just 1.5 blocks to the stunning Gulf beaches and only a few blocks from the bay, City Pier, and all the boutique shops, eateries, and island favorites Anna Maria is known for. No need for a car – you’re just a flip-flop stroll to it all!

Popular amenities for Anna Maria family-friendly rentals

When is the best time to visit Anna Maria?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$99,330 GYDG$127,979 GYDG$190,715 GYDG$139,481 GYDG$104,558 GYDG$117,942 GYDG$131,534 GYDG$94,521 GYDG$87,202 GYDG$79,883 GYDG$95,148 GYDG$108,113 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

Quick stats about vacation rentals that are family-friendly in Anna Maria

  • Total vacation rentals

    Explore 480 vacation rentals in Anna Maria

  • Nightly prices starting at

    Anna Maria vacation rentals start at G$2,091 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,710 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 160 rentals that welcome pets

  • Vacation rentals with a pool

    410 properties feature pools

  • Rentals with dedicated workspaces

    280 properties have a dedicated workspace

  • Wi-Fi availability

    480 of Anna Maria vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Anna Maria rentals

  • 4.8 Average rating

    Anna Maria stays are highly rated by guests—averaging 4.8 out of 5!

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