
Family-friendly holiday 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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Popular amenities for Anna Maria family-friendly rentals
Family-friendly home rentals with a hot tub

Spacious Home Solar-Heated Pool and Spa
Great value!! We loved the pool area and very quiet neighborhood!

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens
Beautiful house and pool area. The back is private with plenty of space. Jeff was always responsive and everything was as described. The girls being able to get eggs every morning was an added touch of experience for them. The house was clean and we had everything we needed for the ten day stay. Tarpon Springs is an annual tradition and we weren't disappointed.

ROYS PLACE Romantic, Private, Paradise!
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.

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209
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!

The Oasis
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.

Waterfront condo on top floor @ Boca Ciega Resort
We had a really nice stay. Well stocked home. Down to Q Tips and needed to purchase nothing in order to stay comfortably. Nice pool and hot tub and great work out room. Loved it!

Tropical Paradise
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!

Private Pool, Jacuzzi, Walk to Beach.
Robert was a great host! Lots of great local recommendations. His place was extremely clean and had everything you could need. Well stocked with essentials. Close to Indian Shores Beach and Clearwater Beach. Had chairs, umbrella and cooler to use at the beach, great amenity!! You won’t be disappointed!! Highly recommend to stay at Roberts place and we plan to be back soon!!
Family- and pet-friendly home rentals

Paradise Retreat
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!!

Newly Remodeled Beachfront Studio - On the sand!
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.

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

2bed/2bath with POOL house, close by SIESTA KEY!!!
The house was exactly as described and was private and clean ! We loved the pool and how quiet and peaceful the neighborhood is . Very much enjoyed our stay as first time guests .

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!
My stay at Stephanie's property was very pleasant. I never had to call her. Everything at her property is excellent. The house is spectacular, the pool was GREAT!!!, and the fire pit was the best. I have no hesitation in recommending her property. Thank you, Stephanie!

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

The Cottage, very close to Siesta Beach!
Fair price. Great Location. Awesome / quick communication.

Paradise Cottage Largo Beaches 1 mile safe private
Mike and Ron are amazing! Their place IS paradise. The house the space everything is so cool and not a single detail missed. The garden is enchanted and sitting in it, you feel like you are in another world. Their house is beautiful full of history, art culture and life. I loved every second of staying here. I felt like I was home finally after a very long journey. Mike and Ron are magic and their space reflects that fully. I will cherish the conversations and moments spent here forever. Thank you god for this moment exactly as it is ❤️
Family-friendly home rentals with a pool

Steps from the beach
We loved it here! It was a quick walk to the beach, and had everything we needed! (Umbrella, beach chairs/towels) The condo was well kept and clean! Restaurants and Publix within walking distance. (Skinny’s was a family favorite) We would definitely book again. It was definitely a stress free, peaceful vacation!

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

Spacious renovated 2-bdrm a short walk from beach
Our family of four drove down from Connecticut and this place was so beautiful and relaxing after a 22 hour drive. It was exquisitely decorated and had every amenity we could possibly need. The host called us as soon as we arrived to make sure we were satisfied with the place and to give us some great recommendations for local restaurants and attractions. It is perfectly situated just minutes from the beach, walking distance to several restaurants, drugstores, a Publix, and the pool was just steps from the door. I highly recommend for any family looking for a beach getaway to make amazing memories.

Pool & fenced-in yard in downtown edge bungalow
We loved it. Great place, great location and very cute, especially if you appreciate the quality and sturdiness of older homes. The pool is a huge bonus. Check in/checkout and everything in between is very easy and convenient.

Sunset and beach view from your balcony Unit 403
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.

Thanksgiving Availability! 1/2 Block-Beach Access
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!

Happy Island Cottage - Private Pool
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!

Castnetter Beach Resort 5
We really enjoyed our stay at the castnetter. It was very clean with all the comforts of home and great location right across the street from the beach. Alan was great and easy to communicate with. Would definitely recommend his condo for rent.
Quick stats about holiday rentals that are family-friendly in Anna Maria
Total rentals
440 properties
Nightly prices starting at
$170 AUD 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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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park