Kid-friendly holiday rentals in Siesta Key

4.94 out of 5 average rating, 289 reviews

Lovely Guest Studio • 6 Miles to Siesta Key Beach

Welcome to your peaceful retreat.Unplug and relax in this bright, cozy studio just minutes from everything Sarasota has to offer. Whether you’re here for business or leisure, this serene space is designed to help you feel calm, refreshed, and right at home. Comfortable queen-bed , Kitchenette with fridge, microwave, and essentials, Full private bathroom and Private entrance, 100 ft from the main house Prime location near restaurants, shops, beaches & downtown quiet enough to relax. Shared pool

4.93 out of 5 average rating, 514 reviews

Guest house in Sarasota

La Casetta: "the little house" near to the beaches

La Casetta means, in Italian, little house. Set in a private, peaceful, mature Florida tropical garden, a real hideaway. I am proud of the cleanliness of our property, however in this new reality that we live in, we do carry out enhanced cleaning and sanitizing between guests. We also practice social distancing, insofar as guests have their own part of our luscious back garden as well as your own entrance. La Casetta has 1 queen sized bed, bathroom & kitchenette. Wifi & Netflix available.

4.9 out of 5 average rating, 117 reviews

Apartment in Siesta Key

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

4.99 out of 5 average rating, 178 reviews

Guest suite in Sarasota

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

4.89 out of 5 average rating, 219 reviews

Tiny home in Sarasota

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

4.87 out of 5 average rating, 112 reviews

Apartment in Sarasota

Anchor house +6 min. from Siesta Beach+heated pool

★ "Ground floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" 🌴 Stylish Retreat Near Siesta Key Heated Pool! Welcome to your perfect Sarasota getaway! This 600 sq. ft. pet-friendly home offers a heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

4.97 out of 5 average rating, 317 reviews

Apartment in Siesta Key

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

4.9 out of 5 average rating, 329 reviews

Guest suite in Sarasota

Siesta Keys stylish and affordable Airbnb.

Relax while you stay in a colorful and warm Siesta Key/Sarasota neighborhood home that is only minutes from the famous Siesta Key beach. Enjoy your private, safe, and comfortable suite while being in close reach to all that Florida has to offer. Your suite is spacious and accommodating, wether your an individual, couple, family, or group of friends we have the space and amenities for you to maximize both your comfort and fun time while here in Florida :-)

Home in Indian Beach-Sapphire Shores

4.9 out of 5 average rating, 662 reviews

Charming Apt. in old Florida home

Cozy, charming suite in a historic 1920's home. Lots of character and charm. Amazing location. One block from the bay with beautiful sunsets. And just a few miles to the beach and downtown. Clean, comfy and a welcoming host. Great for 1 or up to 3 guests. ****Please read the full detailed description for more information before booking. This is very old home, not fully restored, old Florida house. Owner occupied Non- Smoking guests 🙏 Hope to see you soon

4.94 out of 5 average rating, 106 reviews

Apartment in Siesta Key

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

4.97 out of 5 average rating, 326 reviews

Island in Sarasota

Now NEW AUG Openings! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and 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!

4.94 out of 5 average rating, 247 reviews

Guest suite in Sarasota

2 Miles to Siesta Key

Comfortable Accommodations with Private Entrance & Quiet Surroundings. This is a Private Guest Suite in a home with a king size bed, full bathroom, and kitchenette with sink and countertop, fridge and freezer, microwave, and coffee maker. This provides ample utility to prepare simple meals but is not suitable for cooking since there is no stove or oven.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Flats

Convenient locations with everyday essentials

Popular amenities for Siesta Key family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Kid-friendly house rentals

4.97 out of 5 average rating, 67 reviews

Sun-filled cottage with pool, walk to beach

JulietteRating, 5 stars1 week ago

We loved staying here! The house was very clean and we felt right at home! We absolutely LOVED the backyard area with the private pool! The location was very walkable! The owner’s were very responsive and kind!

4.97 out of 5 average rating, 67 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

KyleRating, 5 stars4 days ago

A beautiful home with a private, relaxed atmosphere and all the amenities you could need.

4.93 out of 5 average rating, 355 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

KatherineRating, 5 stars3 weeks ago

We had a wonderful experience in this home. The pool was a blast, baby safe inside and out of the house, quiet neighborhood and close to many fun things to do.

5 out of 5 average rating, 101 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

Rahul VarmaRating, 5 stars3 weeks ago

This place was absolutely perfect for our vacation in Sarasota. The host Landon, had been extremely responsive and the amenities they provided were top notch (from the pool to the mini golf, the beach gear, the coffee machine and all). Will definitely recommend this place to anyone looking for a family getaway to Sarasota.

Superhost

4.86 out of 5 average rating, 50 reviews

Cozy Coastal - 2bd/2bath with Heated Pool and Spa!

BenRating, 5 stars1 week ago

Nice place, convenient location. Great pool for kids

5 out of 5 average rating, 66 reviews

Siesta Key Fully-Renovated Unit 5 min to the beach

KadieRating, 5 stars1 week ago

Amazing host! Super communicative and friendly. I would definitely book again in the future!!

4.95 out of 5 average rating, 91 reviews

1 Bed 1 bath 7 mins to the beach

LauraRating, 5 stars2 weeks ago

Near Siesta Key, a quiet neighborhood. The house has everything you need to cook and be comfortable. Keep in mind that if there are more than two people, the third must sleep on an inflatable mattress (very comfortable, but to be taken into account). My son slept very well there.

4.92 out of 5 average rating, 367 reviews

Home in Bradenton

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

AlejandraRating, 5 stars1 day ago

Great place to stay !! The house is beautiful, it’s in a great location and I love the pool area, I had so much fun with my friends on this trip and we’re planning to come back !!

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Family-friendly apartment rentals

5 out of 5 average rating, 188 reviews

Modern Luxury Apartment in a House Near Siesta

BrandonRating, 5 stars6 days ago

Nick and Jess were wonderful hosts. Responsive to questions. Provided beach amenities. Clean and modern home. Great location as well. 10/10.

4.84 out of 5 average rating, 238 reviews

VILLA 5 · Pool view. King bed. Daily rentals

BruceRating, 5 stars2 days ago

Great place close to the beach and refreshing pool! Enjoyed great meals at Captain Curt’s and Mango Cafe only 10 minute walk away. 7Eleven was close by and handy for beach snacks. Beach chairs provided were much appreciated. Met nice fellow travelers while enjoying morning coffee by the pool. All new interiors had all we needed.

4.81 out of 5 average rating, 242 reviews

Flat in Siesta Key

Cozy, Remodeled Studio Steps from Siesta Key Beach

MattRating, 5 stars1 week ago

Perfect spot right across from Sarasota Beach! Quiet, very clean, great pool, and very responsive host! We loved our stay and have favorited Vanessa as a host so we can check out her properties when we come back. Highly recommend this host and property for your trip to Siesta Key.

4.86 out of 5 average rating, 197 reviews

Updated Old Florida Studio Getaway in Central SRQ

SalRating, 5 stars1 week ago

Detailed, nice place, nice bathroom, all the channels you need for comfort, close to the beach, hashtag cafe has the best matcha I’ve tried. Thanks

Flat in Downtown Sarasota

4.85 out of 5 average rating, 323 reviews

Sarasota Downtown close to Lido Beach

PeterRating, 5 stars1 week ago

Cute little studio apartment nestled in a quite neighborhood close to all shops and beaches in Sarasota, a great couples getaway location.

4.93 out of 5 average rating, 108 reviews

Flat in Siesta Key

Siesta Premier Location - The 'Calm of Siesta'

JasminRating, 5 stars1 week ago

I visit Sarasota every year and stay each time at a new place. This year I wanted to do something closer to the beach and Siesta Village. Matt’s spot was perfectly located for this due to being so close to the beach and every night we walked to the village for dinner/nightlife which was about 15 minutes walking distance. Overall a great place for 1-4 people if you’re looking for a nice chill vacation.

Superhost

4.87 out of 5 average rating, 115 reviews

Cozy Updated Studio Apt-Centrally Located!

KateRating, 5 stars2 weeks ago

Garrett went above and beyond in assisting us during our stay. Replied within minutes when there was a question. The space was spotless, very update and very comfortable. The outside area has a lovely array of fauna, shaded area, and a hot tub. Definitely recommend this space.