Family-friendly vacation rentals in Anna Maria

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Popular amenities for Anna Maria family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
A wooden walkway leads through natural dunes towards a sandy beach. Umbrellas and chairs are set up along the shoreline, while gentle waves reflect the blue sky and clouds. Lush vegetation flanks the path, creating a serene coastal entrance.
Condo in St. Pete Beach
4.88 out of 5 average rating, 149 reviews

Sun, Beach Views, and Smiles!!!

KimRating, 5 stars1 month ago
Fabulous space with an outstanding location. Walked to get all groceries and eat at wonderful restaurants. Pool area was nice with afternoon sun and just steps to the beach. Thanks Margie!
Top guest favorite
A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.
Home in Tarpon Springs
4.96 out of 5 average rating, 362 reviews

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

DavidRating, 5 stars2 weeks ago
Overall our stay was great! Jeff was very responsive, and left us a lot of recommendations for local restaurants. The house was very clean and the pictures accurately reflected how to house looked. The only downsides were the large bugs that somehow got in the home. There were 3 occasions this happend but they seemed harmless. The net around the pool had a tear in it allowing spiders and lizards inside of the pool area but they stayed around the outside of the pool so we could avoid them.
Top guest favorite
The enclosed pool area is surrounded by lush greenery and tropical plants, with vibrant purple lighting creating a serene ambiance. A spacious swimming pool reflects the colors overhead, while a decorative wall clock adds a charming touch. Comfortable seating is present along the edges.
Apartment in Indian Beach-Sapphire Shores
4.96 out of 5 average rating, 168 reviews

ROYS PLACE Romantic, Private, Paradise!

KellyRating, 5 stars1 week ago
Roy’s place was comfortable, had good amenities, good location ( multiple beaches and restaurants in a close radius). The house was beautiful and just as described. The pool/hot tub, and outdoor seating was private and well maintained. Chairs, umbrella, and cooler were available to use which was a nice plus. We would definitely love to stay at this place again. Roy was quick to respond to any questions we had.
Top guest favorite
A serene balcony offers a view of the waterfront, with two green chairs and a glass table positioned to enjoy the scenery. Palm trees are visible in the foreground, and the calm water reflects the bright blue sky, creating a tranquil outdoor space.
Condo in St. Petersburg
4.98 out of 5 average rating, 268 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

SarahRating, 5 stars1 day ago
Just like the photos! Beautiful and comfortable for our stay… Love the location, close to everywhere we wanted to go! Comfortable bed, the couch could use some updating. The pool is very warm, but a nice spot to hang out. Didn’t get to see any dolphins 😞 Overall, enjoyed our stay, will definitely be back!
Guest favorite
A modern kitchen showcases white cabinetry with marble countertops and stainless steel appliances. Natural light floods through large windows, highlighting decorative accents and elegant floral arrangements. A central island is surrounded by bar stools, complemented by stylish area rugs beneath.
Townhouse in Clearwater Beach
5 out of 5 average rating, 121 reviews

Waterfront Beach House Steps Away from #1 Beach!

RyanRating, 5 stars3 weeks ago
Beautiful townhouse and accommodations were excellent! Very clean, close to the beach and surrounding stores and restaurants. Loved that we were able to use their wagon and beach chairs as well as the bikes to get around. Would definitely stay here again!
Guest favorite
A balcony area features a round wooden table surrounded by two chairs, one woven and one metal. A decorative piece is displayed on the wall, with two fishing poles leaning against the balcony railing overlooking the water and marina.
Apartment in St. Petersburg
4.9 out of 5 average rating, 170 reviews

The Oasis

CherieRating, 5 stars2 days ago
Russell’s place was just as described. The bay of the bay was beautiful! This condo was within short driving distances of many great local beaches and restaurants. It had all the amenities, linens, and other items needed to make our stay perfect. Russell checked in with us prior to our stay, during and after.
Superhost
A spacious balcony offers water views featuring palm trees and lounge furniture. The exterior of the building showcases a light-colored facade. A living area is furnished with a soft couch and a dining set, bathed in natural light from large windows. A pool area is visible with lounge chairs and palm trees lining the water's edge.
Condo in St. Petersburg
4.85 out of 5 average rating, 461 reviews

Waterfront condo on top floor @ Boca Ciega Resort

RaymondRating, 5 stars3 weeks ago
Her voice was very nice.The swimming pool area was very nice.We really enjoyed our stay. if I was staying in the area I would definitely stay again.Thank you very much for the hospitality
Top guest favorite
Apartment in Dunedin
4.99 out of 5 average rating, 244 reviews

Tropical Paradise

NancyRating, 5 stars1 week ago
Perfect oasis for a tropical getaway! Everything was just as described. Really enjoyed the use of bikes and Honeymoon Island is absolute paradise! Lori ands Gary were very attentive and quickly handled anything we needed!

Family- and pet-friendly home rentals

Guest favorite
A private tropical heated pool is framed by lush greenery and palm trees. A lounge chair with a colorful towel rests beside the tranquil blue water. The inviting pool area is enclosed in a screened area, enhancing privacy and comfort.
Home in Bradenton
4.95 out of 5 average rating, 258 reviews

Paradise Retreat

TeresaRating, 5 starstoday
Maggie’s place is perfect!! So convenient to everything you need!! Everything in house that you would need and also everything you need to go to the beach!!! Maggie is very fast to responding to any questions you have!! 5 star for sure!!
Guest favorite
A spacious bed is centered in the room, layered with neutral-colored bedding and decorative pillows featuring floral patterns. Flanking the bed are two bedside tables topped with lamps, and a large piece of artwork depicting a beach scene hangs above.
Apartment in Bradenton Beach
4.9 out of 5 average rating, 126 reviews

Newly Remodeled Beachfront Studio - On the sand!

AnnetteRating, 5 stars3 days ago
Jeffery’s rental was perfect. He has such an eye for detail and it’s beautifully decorated. Our view of the ocean from the sitting area outside the rental was spectacular! The space contained everything you would possibly need and was extremely comfortable. This is our second stay at Shell Cove 1 and we highly recommend it to others.
Guest favorite
A wooden boardwalk leads directly to the beach, framed by sandy dunes and swaying grass. The clear blue sky meets the calm waters of the Gulf, creating an inviting scene for beachgoers. The soft beach sand stretches out, blending seamlessly into the horizon.
Cottage in Pass-a-Grille Beach
4.88 out of 5 average rating, 170 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

KatieRating, 5 stars2 weeks ago
Lisa was a great host, and paradise by the beach is an awesome place to stay. My family of 4 (2 adults and our older teens) just loved being able to have a lot of space (compared to the hotel rooms on st Pete beach) and a full kitchen and a close walk to the beach. The kids loved riding the bikes to get an ice cream at night, and it was so easy and convenient to pack up the chairs and umbrella and walk over to the beach. The walk is actually shorter than the resorts we have stayed at on spb. It was kind of like settling into our home by the beach—very comfy and convenient with everything we needed. Lots of tvs, lots of space, easy to get around. I also liked having a fully equipped kitchen—only made dinner one night, but everything we needed was there! We’d definitely again and prefer it to the other resorts we have stayed at. It’s less expensive, more convenient, and a lot more space. Thank you so much, Lisa! We hope your space is available next time we come down!
Guest favorite
A vibrant courtyard is filled with tropical plants, colorful lounge chairs, and a tiki bar. Unique garden decorations and a fish pond with a waterfall enhance the lively atmosphere. Striped umbrellas provide shade over the seating areas, creating a welcoming outdoor space.
Townhouse in Gillespie Park
4.95 out of 5 average rating, 367 reviews

Peacock🦚1/2 m Walk to Downtown #TheTropicalNut ☀️🥳👙

RanceliRating, 5 starstoday
I would definitely stay here again and again. We were delighted. Everything was very clean. The house is beautiful and very cozy. Jennifer is a lovely person, very attentive to everything and pleasant. If you're planning on going to the beach and staying in an Airbnb, do it here because this house is perfect for the occasion.🥰♥️
Guest favorite
A screened-in pool area features a crystal-clear heated pool with lounge chairs positioned nearby. An umbrella provides shade over a seating area, surrounded by lush greenery and fencing that enhances privacy.
Home in Sarasota
4.95 out of 5 average rating, 211 reviews

2bed/2bath with POOL house, close by SIESTA KEY!!!

EmilyRating, 5 stars2 weeks ago
We absolutely loved our stay here! The house is beautiful and has everything we needed for vacation. The pool was perfect for the kids - they preferred staying home at the pool than going the beach. Romulda was also so helpful and responsive to all our questions. We only wished we had more time to stay here! We’re looking forward to booking again in the future!
Top guest favorite
A spacious saltwater pool is framed by a tiled deck, with seating options including lounge chairs and colorful adirondack chairs. The tiki bar offers a shaded space with additional seating, while the bungalows can be glimpsed in the background, creating an inviting outdoor atmosphere.
Home in Seminole
4.97 out of 5 average rating, 193 reviews

4BR/3BA Pool Home 7mins to Madeira Beach-Sleeps 14

BenjaminRating, 5 stars2 weeks ago
For those traveling to the area, this is the perfect spot! My family and I had a wonderful time and Stephanie and team were always there if we needed anything! Home is very close to the beach, plenty of places to sleep, beautifully designed, and in a great neighborhood. Would definitely plan to stay here again!
Superhost
A secluded backyard features a heated pool surrounded by lush greenery and flowering plants. Tropical palm trees and colorful potted plants enhance the tranquil atmosphere, while the tiled pool edge adds a touch of contemporary design.
Home in Sarasota
4.82 out of 5 average rating, 255 reviews

Private Siesta Beach House Oasis with Heated Pool.

AmandaRating, 5 stars2 weeks ago
We loved staying at Andrew’s Airbnb - we kept saying how everything we wanted to do, no matter which direction was 15 -20 mins max from the house! The backyard is like an oasis, we enjoyed it so much and so did our pups!
Guest favorite
Bungalow in Indian Shores
4.9 out of 5 average rating, 205 reviews

Private Beach Bungalow 1BR *Heated POOL**PETS ok

Josh and Sarah Rating, 5 stars1 week ago
We recently wrapped up an AMAZING stay at The Lobster Beach Bungalow. Everything was as described- charming ‘old Florida’ feel and close proximity to the beach (50 steps). It felt like a miniature resort. We got to meet other vacationers staying at the other bungalows, which was pretty cool. We were even able to enjoy the pool on a day where the gulf waters were a little rougher. There are a lot of eateries within walking distance. We tried a different coffee shop every morning- yum! The bungalow itself was comfortable and had everything we needed for a great stay. The kitchen had we could have desired should we have decided to eat in. Too many yummy local eateries for that for us though! We also loved being able to have our fur babies with us, as no vacation is complete without our whole family. We look forward to returning next year with some extended family to experience this peaceful paradise. Thank you, Liz, for creating a place that feels like home away from home!

Family-friendly home rentals with a pool

Guest favorite
A single-story townhouse features a welcoming entrance flanked by two sets of glass doors. Lounge chairs are positioned on a freshly manicured lawn, surrounded by shrubs and palm trees. Blue skies are visible above, enhancing the inviting setting.
Home in Siesta Key
4.77 out of 5 average rating, 512 reviews

Beachfront Getaway in Siesta Key

AdairRating, 5 stars1 week ago
Our stay was so easy and enjoyable! Dior’s place is so cute and very clean. We were able to walk to multiple shops, bars, and restaurants. It was so nice to have our private beach access right down the sidewalk, and right beside the pool! We were also so glad that she was able to accommodate us on such short notice. Everything was perfect! This will definitely be our go-to place to stay when we visit Siesta!
Superhost
A screened-in patio features a round table surrounded by six bright red chairs. A ceiling fan is visible above. A peaceful lake view is framed by trees, with landscaped grounds and additional buildings in the background.
Apartment in Bradenton
4.9 out of 5 average rating, 31 reviews

PN-near Beaches and IMG, Pool, Tennis, Pickleball

LoisRating, 5 stars1 month ago
Absolutely worth it. We spent time on Manatee Beach, had great dinners at the Ugly Grouper, Anna Maria’s Oyster House and Marina Jacks which was more upscale. The house was super clean and very comfy. Last eve was spent in pool and hot tub. Also owners were responsive to any requests. i would recommend this place and stay again myself. We also rented a catamaran 3 hour tour 😉 at Kathleen D’s. very nice.
Superhost
Home in Bradenton
4.83 out of 5 average rating, 78 reviews

4/2 Home Heated Pool/close to Anna M. Beaches/ IMG

SusanRating, 5 stars1 week ago
We had a GREAT time at this house! Pool area was AMAZING! Great for a family with kids, plenty of beach toys/coolers/lawn chairs. I would definitely stay here again.
Top guest favorite
An open living area showcases white seating arranged around a coffee table, with a view of the pool and waterfront. Ambient lighting is provided by ceiling fans. The space opens to an outdoor patio, featuring colorful lounge chairs surrounding the pool, enhancing the serene atmosphere.
Home in Coquina Key
5 out of 5 average rating, 19 reviews

Hidden Gem in Paradise with Private Beach and Pool

KathyRating, 5 stars1 week ago
The home was absolutely beautiful, well stocked, and perfect for our needs. John was extremely responsive to our few questions.
Guest favorite
A private tiki hut features a thatched roof, ambient lighting, and a large television. Seating is provided by several lounge chairs and a unique wicker chair, arranged around a stone floor. Lush greenery surrounds the area, enhancing the outdoor experience.
Bungalow in Indian Rocks Beach
4.88 out of 5 average rating, 119 reviews

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

KristaRating, 5 stars1 week ago
We just had the best family beach vacation at Mindy's place! The location cannot be beat. A very short walk to the beach with ice cream on the way. The pool was so nice to use every day as well. We really appreciated the outdoor shower by the pool to rinse off after the beach as well. The beds were soft and cozy and had everything we needed. We have small kids and so we really appreciated the beach wagons, toys, life jackets, and umbrellas and couldnt have done the beach without them since we flew in. The house is so cute and tropical and really felt like we were on vacation! My kids favorite part was the pool! Mindy went above and beyond to make sure we had everything for our stay and we really appreciated it! Cannot recommend this place enough!
Superhost
A clear heated pool is seen with shimmering blue water, accompanied by several lounge chairs positioned around the poolside. The area is landscaped with greenery, and a shaded pavilion is observable in the background.
Condo in Longboat Key
4.86 out of 5 average rating, 99 reviews

Sunset and beach view from your balcony Unit 403

NickiRating, 5 stars1 month ago
This place was just what we needed for some rest and relaxation. Everything was exactly as listed. Extremely clean and well supplied with towels and all your kitchen needs. The views from our balcony and the sounds of the ocean were priceless. If you’re looking to get away from it all and disconnect, this is the place!! You will not be disappointed.
Top guest favorite
A refreshing pool is surrounded by lounge chairs and tropical greenery, offering a relaxing outdoor space. The vibrant blue exterior of the condo stands out against the palm trees, while beach access is visible in the background, ensuring proximity to the sandy shores.
Townhouse in Bradenton Beach
4.96 out of 5 average rating, 79 reviews

Thanksgiving Availability! 1/2 Block-Beach Access

TaylorRating, 5 stars1 week ago
This was the perfect beach house getaway for my family. The house was well stocked with everything you would need in the kitchen, bathrooms, bedrooms, and even pool/beach supplies. The beach was only short walk across the street. The pool was amazing and probably our favorite spot to hangout. Will definitely look into booking Anna’s place again because it’s a gem!
Guest favorite
Home in Holmes Beach
4.93 out of 5 average rating, 68 reviews

Happy Island Cottage - Private Pool

GlenRating, 5 stars1 month ago
Our family had a great time! The house and pool are awesome. And the location is great! Walk to the beach, the Ugly Grouper, bait shop, convenience store, fresh seafood store, etc. Hosts are proactive but not intrusive. Highly recommend!

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

  • Total rentals

    440 properties

  • Nightly prices starting at

    G$23,006 GYD before taxes and fees

  • Total number of reviews

    6.7K reviews

  • Pet-friendly rentals

    140 properties allow pets

  • Rentals with a pool

    380 properties have a pool

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

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