Family-friendly vacation rentals in Holmes Beach

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Top-rated family-friendly rentals in Holmes Beach

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

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Guest favorite

Home in Bradenton Beach

4.91 out of 5 average rating, 234 reviews

Ohana Beachside 2 Br Gulf view - 150 ft from Beach

Aloha and welcome to our island home. "Ohana" is Hawaiian for family & that is who you are when you stay w/ us. The 2 bedroom 1 bath suite is located on the second floor w/ picturesque views of the Gulf from the living room, 2nd bedroom & your outside deck. 4 PPL ONLY! We also have a 3rd floor deck guests utilize to watch the sun sink into the earth over the Gulf of Mexico or enjoy soaking up the sun. You are 150 feet from stepping into the pristine white sands & turquoise waters of the Gulf.

Dec 12 – 19

R3,624 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.

Dec 7 – 14

R9,790 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

R8,614 ZAR per night

Guest favorite

Condo in Holmes Beach

4.86 out of 5 average rating, 109 reviews

Steps from the beach

Perfect place to put your feet up and relax! One of four units in the condo gives your getaway a private feeling where you don't share the heated pool with many others, on a dead end road. The only unit overlooking the pool from the master bedroom. You'll be just one block from the beach making it tempting to go multiple times a day! The clean, modern decor makes it a great place for both short and long term visitors. Just a nature trail away from a grocery store, shops and restaurants.

Dec 21 – 28

R4,797 ZAR per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

Dec 2 – 9

R2,483 ZAR per night

Guest favorite

Condo in Holmes Beach

4.96 out of 5 average rating, 116 reviews

Beautiful beachfront condo for perfect vacation

Beautiful, cozy, elegantly furnished, spacious (1350 sqf with a large terrace), beachfront, 2 bedroom - 2 bathroom condominium, in the best managed, boutique-style gulf front residential complex on Anna Maria Island in Florida for an ideal vacation. Heated pool and hot tub, 2 tennis courts, 2 elevators, top floor unit, high speed internet, washer/dryer in unit, beach chairs, close to supermarket (Publix) and restaurants, free island trolley, rich cultural life.

Jul 20 – 27

R4,853 ZAR per night

Guest favorite

Apartment in Holmes Beach

4.95 out of 5 average rating, 172 reviews

Cabin 2 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, the free AMI trolley, and nightlife. You’ll love my place because of the location and the ambiance. It is nestled in the lush tropical landscape of Spinnakers Vacation Cottages. You will find Cabin 2 is a perfect spot for an island getaway. My place is good for couples, solo adventurers, families (with kids), and certain size breed and weight dogs. Spa maintains same temperature as pool.

Sep 21 – 28

R4,709 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

R2,566 ZAR per night

Guest favorite

Condo in Longboat Key

4.8 out of 5 average rating, 212 reviews

SRQ/Longboat Key Beach - kid friendly/romantic B1

Beachfront on beautiful Longboat Key, this condominium, unit 234, offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air.

Nov 16 – 23

R3,689 ZAR per night

Guest favorite

Guesthouse in Sarasota

4.97 out of 5 average rating, 234 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

R3,112 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.

Jun 5 – 12

R2,350 ZAR per night

Guest favorite

Condo in Bradenton Beach

4.89 out of 5 average rating, 120 reviews

Your Tropical Paradise Destination

The only thing you will need to bring are your groceries. Our 2nd floor Condo features 781 sq ft, 2 bedroom 1 k bd, and 1 full size bed, 1 bath, full kitchen, dining and living room, patio with breathtaking views of the Gulf of Mexico. Washer and dryer in unit! Grocery shopping / special request available upon request, before your arrival.

Aug 13 – 20

R3,633 ZAR per night