Family-friendly vacation rentals in Anna Maria

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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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Guest favorite

Apartment in Treasure Island

4.86 out of 5 average rating, 279 reviews

Treasure Island Beach Apartment #3

Great location, directly across Gulf Blvd from the 123 Street beach access with, Boca Ciega Bay behind. Your home is a full sized one-bedroom apartment with all the amenities, including a sleep sofa for the occasional guest. The beach is the main attraction, along with plenty of activities to choose from, like fishing, swimming and sunning. Walk the beach or to restaurants and shopping at nearby John's Pass. Live music every night. Year round golf. Off street parking available for one vehicle.

Nov 21 – 28

R2,140 ZAR per night

Guest favorite

Home in Anna Maria

4.93 out of 5 average rating, 153 reviews

Private 30' Pool and Boat Dock - Rated best on AMI

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles than staying at Sunshine Cottage, located in the City of Anna Maria!

Dec 1 – 8

R9,839 ZAR per night

Guest favorite

Apartment in Holmes Beach

4.97 out of 5 average rating, 185 reviews

Crows Nest at Spinnakers Vacation Cottages

Close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love the location, the ambiance, and the high ceilings. Located in the lush tropical paradise of Spinnakers Vacation Cottages. Offers a spacious living area, with the bedroom and bathroom on the living floor with a spiral staircase leading to a loft with two twin beds. Great for couples, families and dogs (with small pet fee) Great private deck for star gazing! Spa maintains same temperature as pool

Jan 4 – 11

R5,561 ZAR per night

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

*NEW May 17 CX 30% OFF! Sarasota #1 Luxury Villa*

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Jan 6 – 13

R11,668 ZAR per night

Guest favorite

Home in Holmes Beach

4.97 out of 5 average rating, 124 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly (to 35 lbs) in a great location 5 min. walk to the beach. Private lagoon-style *heated* pool amid lush landscaping with gorgeous rock waterfall. Fully updated kitchen, 60-inch Sony HDTV, 55'' Samsung Frame TV, Italian leather reclining sofas, BBQ, beach gear, updated bathrooms, three king bedrooms. Classic Florida one-level home - no stairs. Managed directly by owners. No crazy fees!

Aug 31 – Sep 7

R8,470 ZAR per night

Guest favorite

Home in Bradenton Beach

4.97 out of 5 average rating, 153 reviews

Paradise! Steps2 Private Beach & Tropical Yard!

Less than a 2 minute WALK from the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. With large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with a bathroom on opposite ends of the house (a pocket door adds privacy). Private heated salt water pool sits amidst the lush tropical yard. Hop on the free A/C'ed trolley and explore Florida's gorgeous Anna Maria Island.

Apr 26 – May 3

R12,730 ZAR per night

Guest favorite

Guest suite in Gulfport

4.92 out of 5 average rating, 454 reviews

Gulfport Studio STEPS to Beach & Restaurants

Calling all beach lovers! Fall in love with this unique Gulfport Beach Cottage! Colorful, light & bright. Located on a corner lot STEPS from popular Beach Blvd & Gulfport beach, fishing pier, eclectic Gulfport shops, cafes and everything FUN! Gulfport has artsy and quirky shops, fabulous waterfront restaurants and a thriving art scene. Gulfport is a funky community all its own. Gulfport has an Art Walk on the First Friday and Third Saturday and a Tuesday market every week. Don’t miss it!

Oct 10 – 17

R2,281 ZAR per night

Guest favorite

Guest suite in Bradenton

4.81 out of 5 average rating, 145 reviews

Lovely Studio near Anna Maria Island and UTC Mall

Lovely and cozy studio apartment minutes from white sandy beaches, IMG Academy, Sarasota, Theaters, dining and UTC Mall. Located in Bradenton, FL minutes from Sarasota and Tampa. The studio includes a private separate entrance, private bathroom, wifi, a kitchenette with full -size fridge, Keurig, and stove top. Minutes from Anna Maria Island, Coquina Beach, Bradenton Beach, Holmes Beach, award-winning Siesta Key Beach, LECOM Park and 15 minutes from St. Armand’s Circle.

Feb 13 – 20

R1,580 ZAR per night

Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 143 reviews

1 BR direct beachfront! Now avail. 8/29-9/11.

Our condo is directly on the beach!! It is close to restaurants and dining, mini-golf, Clearwater and St. Pete's Beach. About 25 miles from Tampa, Florida for the Buccaneers NFL football and Lightning NHL hockey! We are about 37 miles from Busch Gardens. Only 95 miles to Disney World in Orlando! Mini-golf right across the street! You’ll love my place because of the neighborhood. My place is good for couples, small families, solo adventurers, and business travelers.

Dec 10 – 17

R2,712 ZAR per night

Guest favorite

Cottage in Bradenton

4.94 out of 5 average rating, 153 reviews

Cozy Cottage L-Steps to Riverwalk/Close to Beaches

Beautiful cottage style duplex located in Old Downtown West Bradenton in Historic Point Pleasant neighborhood - steps from Riverwalk! Close to beaches!!! Visit RealizeBradenton website for a listing of monthly events , Comfortably sleeps 4 - 1 bedroom with king size bed ,Living area has queen sleeper sofa, Kitchen: well equipped • Guest must disclose if they are bringing a pet and the pet breed • $50 per each 2-7 day stay - per pet

Jul 22 – 29

R2,508 ZAR per night

Guest favorite

Guesthouse in Sarasota

4.97 out of 5 average rating, 235 reviews

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area offers. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

Oct 20 – 27

R3,038 ZAR per night

Guest favorite

Home in Palmetto

4.9 out of 5 average rating, 141 reviews

Historic Home with Boat parking 0.6M of Boat Ramp

Newly renovated home close to everything. 3 bedroom two bath with kitchen, large master suite with smart TV, dressing area, living room & 3 outdoor spaces. Fenced very large private yard. 4K smart TV in Living room. Walking distance to REGATTA POINTE MARINA, Downtown Historic District, Publix and main street eating venues. Easy drive to beaches both Anna Maria Island and St Pete.

May 28 – Jun 4

R2,323 ZAR per night