
Family-friendly holiday rentals in Bay Pines
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Top-rated family-friendly rentals in Bay Pines
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Popular amenities for Bay Pines family-friendly rentals
Family-friendly home rentals with a hot tub

THE HOUSE - 32 Steps to the Beach - Beautiful Clearwater Beach Home just across from the Beach - Drive to your door.
This was our 2nd stay and it was just as pleasant as the first time! The extremely short walk right across the street to the beach, quiet neighborhood, less crowded section of the beach, along with the close proximity to restaurants makes it the perfect little getaway! It's probably the most well stocked home with everything you can think of needing (including both a hot pot and tea pot for your tea, beach towels, beach chairs, wagons, boogie boards ECT) It's a clean, comfortable place that makes us feel right at home. We also love the option of the hot tub to relax in for the evening. The hosts are very kind/helpful. It's the perfect little beach getaway. Thank you again! This place has a special place in our hearts. Happy memories made!

Waterfront Luxury Heated Pool/Hot Tub 5 bedrooms
The house was well stocked and very clean. The pool was at a perfect temperature and also clean. Location was great, close to many restaurants and beaches. Great for a family vacation with little ones. The host was very friendly and easy to communicate with. The only downside (to be expected) is the number of biting bugs in the morning/evening - there were no outdoor screened in areas, and there were a lot of raccoons that came into the backyard at night. Not a great place to spend nights outside, but this is discouraged by the host understandably, as the house is in a neighborhood with mostly locals. All in all it was a great experience and we would recommend it to friends/family, and stay again.

Sun, Beach Views, and Smiles!!!
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!

Crescent Beach House Pet friendly
This was the perfect location for our family. We loved the proximity to the beach and restaurants. The place was clean and well stocked. Would love to come back.

Beach Front Condo 3 bathrooms 3 bedrooms/5 beds
I loved the apartment very well equipped for everything you need to cook. The apartment has an amazing view, location is great, close to everything from restaurants, grocery stores, pharmacies, etc. I loved it!

Waterfront Beach House Steps Away from #1 Beach!
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!

Waterfront Oasis! Kayaks,Hot Tub
The place was wonderful. it was very comfy. Big kitchen with lots of pans to cook in. big fridge and huge TV in all the rooms. AC is on point and works great. The yard, the water, the atmosfere is pretty awesome. Loved it

Bay Shores Yacht & Tennis Club Indian Shores FL
Great location! Easy walk to the beach. Property has desired amenities. Inside had everything we needed.
Family- and pet-friendly home rentals

STEPS TO THE BEACH FROM, 'COZY BEACH COTTAGE
Great location.Everything in the house is perfectly clean.There is everything you need for a holiday.Will come back again.

Vintage Florida Beach Cottage B
We brought two toddlers to the little pink house, and they just loved it. The kitchen was set up Perfect. The Murphy bed in the living room was a bonus and let us all spread out when it was time to sleep. Eric was nearby in a nearby apartment, and so helpful with everything. The best is he provided just the right amount of beach toys, and two wagons to get toddlers to the beach, which is just a block away. If we would’ve stayed longer, we would’ve Used the laundry, which was lovely We discovered night frogs at the fountain around the corner, and the nature park and playground also just a walk away . Great spot

BEACHFRONT Condo - Belleair Beach Club - RENOVATED
Mathew's place was exactly what I needed. Calm, quiet and very peaceful. I didn't hear the neighbors the whole time I was there. The beach was literally right out the window. So getting down there was very easy. Having a beach chair, cooler and bag in the condo was very convenient. The condo was very clean and homey. I liked being able to cook for myself and never having to leave the complex. I will definitely stay here again!!

Cute home in historic neighborhood
The place was cozy, comfortable, and a great value overall. Clean and well-equipped, working AC, fresh sheets, clean kitchen and bathroom, and enough supplies for a short stay. I did find a dead roach when we arrived, but being from Florida, that’s not shocking and didn’t bother me. If you're super particular about spotless perfection, you might notice minor things, but nothing that impacted our comfort. The neighborhood is clearly mid-gentrification so you may see some characters around; I came across a homeless person sleeping in the nearby playground one morning while walking my dog. That said, I never felt unsafe (as a 6 foot tall guy) and it seemed like a “keep to yourself and you’re fine” kind of area. I took my daughter to the playground another day without issue. The best part is the location: 5 min drive (or 10 min scooter ride) to Central Ave, for great bars and restaurants and a 10 min or less drive to the waterfront area.

Villa Al Golfo Pristine Waterfront Oasis
Lyn is a wonderful host and the villa is just amazing! It looked just like the photos, right next to water, 2 minute walk to the beach, sparkling clean, has everything one needs for a wonderful vacation. Lyn was very kind to reach out in advance asking for coffee/cream preferences, and during the stay even offered to buy us dinner just to brighten our stay even more! She is super friendly and easy to talk to, and overall our stay could not have been better.

Gulfport Art District - One Block From Beach!
This may be my one of favorite vacation rentals we’ve done! The owner is super attentive and quick with responding. The place itself is adorable. Amazing location, clean and so charmingly decorated. They have the fridge and cabinets stocked with essentials which is an amazing touch. Already thinking about booking again for a trip in the winter!

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!

Baby Bungalow close to Downtown!
This adorable bungalow was perfect for a long weekend getaway! They have all of the amenities, it is centrally located, it's clean, and they communicated very well. I will definitely come again and recommend your place!!
Family-friendly home rentals with a pool

Renovated Condo! Across the Street From The Beach
being 7 months pregnant this place was perfect for a quick baby moon! the beach is just a walk across the street, plenty of restaurants less than a 5 minute drive and had everything we needed for the beach as well.

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach
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!

Historic Kenwood Studio with Pool
Kenneth’s place is a true gem. Perfect location, amazing surroundings, quiet and safe. The pool area was so serene and inviting, such a lovely little oasis. Kenneth was friendly and available, such a great host. We will definitely return!

POOL VIEW IN A MODERN CONDO - Feel at Home
We had an amazing stay. We loved all the amenities. The condo was gorgeous. A super comfortable bed and pillows. Shower pressure was great and plenty of hot water. It was nice to have a washer and dryer in the unit. The kitchen was well equipped and convenient for breakfast and lunch. We went out to dinner every night because there are so many great restaurants in Clearwater and the surrounding communities. Thank you for allowing us to stay at such an amazing place!

1 BR direct gulf front!
Due to the hurricanes there was still some work going on at the Condo and on the beach. We completely understood and knew this might be the case coming in. Our goal was to relax and unwind and that is what we did! We loved the location - the ocean view from the deck and the short walk to the beach. The bed was relatively comfortable - not too hard. There were plenty of things in the kitchen to make using it easy. We walked and hung out on the beach a lot which was our plan. The pool is small but was nice. There are restaurants and stores within relatively close driving distance. When we had a question everyone was quick to get back to us. Overall a truly wonderful experience!

Villa Madeira
Ray's 3 bedroom condo is very comfortable and relaxing. The master bedroom is well stocked with a variety of books to read. Being right on the beach, it has a great view and very accessible to the ocean. We used the kitchen almost every day to make a meal. The brand-new Samsung refrigerator was a nice perk.

Waterfront, Harbourside, Water Park, Beach, #7720
We had a wonderful stay this past week! The condo was beautiful and very comfortable. We enjoyed both balconies and the views on the bay were fabulous. Our children had a blast at the water park and the beach is just a short walk away. The space was also impeccably clean, which we appreciated very much. Our boys were already asking if we can go back next year!

Comfortable Home w/Private Pool
Matthew was great to work with and we thoroughly enjoyed our stay at his place! If you need a place within walking distance of some beautiful parks, within driving distance of the beach, close to some fantastic restaurants, and with a pool to relax in in the evenings, then this is the place for you!
Quick stats about holiday rentals that are family-friendly in Bay Pines
Total rentals
160 properties
Nightly prices starting at
₹5,995 before taxes and fees
Total number of reviews
7.1K reviews
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
110 properties have a dedicated workspace
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- Anna Maria Island
- Siesta Beach
- Dunedin Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
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- Lido Key Beach
- Amalie Arena
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- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Adventure Island