Family-friendly vacation rentals in Osprey

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Osprey

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

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Guest favorite

A bright kitchen area features pale green walls and modern white cabinetry. A sign spells out "BEACH" in decorative letters, accompanied by textured decorative objects. A stainless-steel refrigerator and microwave are visible, highlighting the suite's inviting and fully equipped kitchen.

Guest suite in Sarasota

4.79 out of 5 average rating, 307 reviews

Studio 10 Minutes to the Beach Fenced in Backyard

Experience Sarasota like never before in our studio. Immerse yourself in the seaside charm while enjoying the comfort of a home away from home. Perfectly situated in the heart of Sarasota, you'll have easy access to all the must-see attractions, from the pristine Siesta Key beach to the bustling downtown area. Plus, with Sarasota Bay, Marina Jacks, top-rated restaurants, and grocery stores just a stone's throw away, everything you need is within reach. Come live the dream & book your stay today!

Guest favorite

A light-filled entryway features a wall of glass shelving with decorative items. Double glass doors provide access to the outdoor space, which is partially visible through the glass. A small mat lies on the floor near the entrance.

Home in Sarasota

4.91 out of 5 average rating, 200 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

Superhost

A serene lake mirrors the surrounding landscape, showcasing greenery and trees along the shoreline. The cloudy sky is reflected in the still water, creating a calming ambiance. The scene emphasizes the natural beauty and tranquility of the property.

Home in Nokomis

4.73 out of 5 average rating, 342 reviews

The Ibis Cottage

Freshly renovated, The Ibis Cottage is a cozy studio on a beautiful property overlooking a small lake. It is a 5 minute drive to Nokomis Beach, Siesta Beach and Venice Beach are within easy reach, and a block away to the Legacy Trail bike path (Sarasota to Venice). Enjoy seeing a variety of birds on the property including the ibis, heron, and snowy egret. The cottage is conveniently located between Sarasota and Venice. The perfect location for enjoying the Gulf coast and outstanding beaches.

Guest favorite

A well-organized kitchenette is presented, featuring a microwave, sink, and open shelving with various containers and glassware. The blue walls enhance the workspace, while a polished wooden countertop reflects ample light from the surroundings.

Apartment in Sarasota

4.8 out of 5 average rating, 109 reviews

Cozy and Private Studio Near Downtown & Beaches

Welcome to your private Sarasota retreat! This cozy and well-appointed studio offers everything you need for a comfortable stay—spacious bath, kitchenette, washing machine, WiFi, cable TV, a comfy recliner, work desk, and wall A/C. Step outside to a fenced backyard with a BBQ grill, perfect for relaxing. Enjoy a private entrance and driveway parking. Just 15 minutes from Siesta Key Beach and 10 minutes from downtown, you’re close to shops, dining, and the Legacy Trail. Relax, unwind, and enjoy!

Top guest favorite

A spacious living area is highlighted by a light-colored sectional sofa adorned with colorful pillows. A large coffee table is positioned in front of the sofa, and a dining table with six chairs is visible in the background. A fan hangs from the ceiling, and natural light enters through nearby windows.

Condo in Sarasota

4.98 out of 5 average rating, 115 reviews

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Welcome to our beautiful condo, which is located just 4 miles to Siesta Key! Enjoy Vamo Park, just steps from our door, where you can launch a kayak or paddle board. Fishing is also allowed from this location. There are also picnic tables at the park where you can enjoy sunset. Our condo is fully equipped with all the necessary things you need. Beach chairs, shops, theaters, gyms, and the legacy trail, Sarasota Sharks Inc. Plus more. These are just a few of the things available in the area.

Top guest favorite

A spacious bedroom features a king-size bed adorned with a blue and white textured coverlet. Soft natural light filters through the window, illuminating the room, which includes a nightstand, dresser, and a comfortable bench at the foot of the bed.

Guesthouse in Sarasota

4.97 out of 5 average rating, 283 reviews

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

Guest favorite

A well-appointed bedroom features a spacious bed with decorative pillows. Soft natural light filters through the window, which is adorned with brown and beige curtains. A vintage mirror adds an elegant touch, while a bedside table with a lamp provides functional lighting.

Guesthouse in Sarasota

4.92 out of 5 average rating, 189 reviews

Cozy Guesthouse in central Sarasota!

This cozy independent guesthouse is perfect for all ocations from a few business day stay to a vacacion getaway. Near to siesta key beach! Enjoy a private room with a comfortable bed, a bathroom with a great shower and hot water, plus a cozy bar-style area perfect for preparing snacks and coffee. You’ll also have access to a small patio where you can unwind, and we provide beach essentials. Perfect for travelers seeking comfort and peace, and a well-equipped space. We’d love to host you!

Top guest favorite

A modern studio layout features a queen bed with a blue floral bedspread, complemented by a comfortable futon and decorative pillows. A small dining table with two chairs is positioned near the seating area, while large blue curtains frame the window, allowing natural light to enter.

Apartment in Sarasota

4.89 out of 5 average rating, 167 reviews

Chic & Cozy Getaway • Near Siesta Key Beach

Renovated modern studio in a duplex home with private entrance, full kitchen, bathroom, laundry, and parking. Nestled in a quiet, safe neighborhood just minutes from Lido, Turtle, Nokomis beaches, and Siesta Key—#1 beach in America with soft, white sand. Walk to restaurants, Starbucks, Total Wine, Costco, Target, CVS, Bay Village Assisted Living, Selby Aquatic Center & Vamo Bay Park. Short drive to downtown Sarasota, Venice & scenic bike trails. Ideal for beach getaways or extended stays!

Superhost

An outdoor seating area is presented with a glass-top table adorned with a vase of fresh flowers. Colorful patterned cushions decorate the two wicker chairs. In the background, a black trailer and a small shed are visible, surrounded by greenery.

Camper/RV in Nokomis

4.79 out of 5 average rating, 219 reviews

Sleep Bird glamping trailer 5min to the beach

Every minute in this romantic home in nature is a pleasure... This little sleeping bird trailer is in the backyard of my house. It is equipped with a bunk bed with full and twin mattresses, refrigerator, coffee maker, electric kettle, microwave, air conditioning and kitchenware. There is also an outdoor wooden shower with a washbasin, a hanging tree swing, a gas grill and a fire pit. You can drive to Nokomis public beach in just 5 minutes.

Top guest favorite

A row of brightly colored Adirondack chairs is positioned on the sandy beach, facing the tranquil ocean. The hues include yellow, orange, green, blue, pink, and purple. A clear blue sky with soft clouds complements the serene shoreline.

Cottage in Nokomis

4.98 out of 5 average rating, 164 reviews

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!

Superhost

A cozy living area is highlighted by a navy blue sofa adorned with decorative pillows. A colorful piece of wall art draws attention, while two pendant lights cast a warm glow. A small white table holds a yellow lamp, and a potted plant adds a touch of greenery.

Bungalow in Osprey

4.78 out of 5 average rating, 360 reviews

Osprey,Buttonwood Cottage.Hot tub -patio.Sublime !

Floridian Tiny Cottage! Buttonwood Cottage is wonderfully located central to the downtowns and beaches of Sarasota and Venice with a private patio space and hot tub. 15 minutes away for the number 1 beach in USA "Siesta Key" . You'll feel that you stepped back in time upon arrival to our charming homestead. I follow Airbnb’s enhanced cleaning protocol, which was developed with expert guidance. Here are a few highlights:

Guest favorite

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

4.97 out of 5 average rating, 334 reviews

RARE Sept SALE! OPEN! 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!