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Family-friendly vacation rentals in Saint Armands Key

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Top-rated family-friendly rentals in Saint Armands Key

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

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The home's exterior is softly illuminated by warm lights, highlighting the paved driveway and tropical landscaping. Tall palm trees and lush greenery surround the entrance, creating a serene atmosphere. The modern roof adds a contemporary touch, enhancing the inviting appearance of the property.

Home in Longboat Key

4.88 out of 5 average rating, 129 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

A tranquil beach scene is depicted, showcasing crystal-clear waters that blend from turquoise to green. A person stands waist-deep in the water, with a horizon extending into the distance. Driftwood and natural debris adorn the sandy shore under a bright blue sky with scattered clouds.

Guesthouse in Sarasota

4.92 out of 5 average rating, 521 reviews

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.

A screened-in patio features a round table with decorative tile and four chairs, surrounded by lush greenery. A pool is visible in the background, reflecting the clear blue sky, providing a serene setting for relaxation and outdoor dining.

Bungalow in Sarasota

4.91 out of 5 average rating, 356 reviews

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with wood floors and lots of natural light, located in a quiet neighborhood on the downtown core edge. Enjoy a spacious and private, fenced-in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

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 Sarasota

4.96 out of 5 average rating, 172 reviews

ROYS PLACE Romantic, Private, Paradise!

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR THREE YEARS. "I LOVE ROYS PLACE!" Words most commonly used by guests in reviews are "quality" "clean" "cute" "sexy" "cool" "safe" . This is a restored 600 sq. ft. one bedroom apartment in an old historic home located in the heart of coveted safe Northwest Sarasota. Offered for you, a romantic boutique apartment with your own private (exclusive to you, not shared) CLOTHING OPTIONAL lanai, outdoor shower and heated pool.

A spacious living area is highlighted by a large sectional sofa and a wooden coffee table. A TV sits atop a media console, while glass doors provide access to the outdoor patio, allowing natural light to fill the room.

Villa in Sarasota

4.89 out of 5 average rating, 208 reviews

Entire Standalone Villa,1.2k sf,1 block Lido Beach

Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!

Top guest favorite

A private pool area is surrounded by lush greenery, featuring a clear blue water pool and four lounge chairs positioned for relaxation. Umbrellas provide shade, enhancing the serene outdoor space. Tropical plants are situated along the edge, adding to the natural atmosphere.

Home in Sarasota

4.98 out of 5 average rating, 106 reviews

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

Your "Beach Home" w/ heated pool is a private home 1 and 1/4 mile drive to Beach Access 12 on Siesta Key. 3bedroom/2bathroom. It's ideal for families/couples. Everything you need for a great vacation!Fully equip kitchen,towels/linen, laundry room . Large pool w/ gas bbq & patio area. Use our chairs, cooler,umbrella,beach cart.STRICT OCCUPANCY OF MAX 6 PEOPLE INCLUDING INFANTS/KIDS AT HOUSE. NO OUTSIDE GUESTS DAY/NIGHT. DO NOT BOOK IF YOUR GROUP IS LARGER. No Pets. Min Age 26 to book

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, 280 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.

Top guest favorite

An outdoor common area features a decorative umbrella over a bistro table, surrounded by potted plants. A wooden deck leads to a staircase, with warm lights illuminating the setting. A grill is positioned nearby, creating an inviting outdoor space for relaxation.

Guesthouse in Sarasota

4.97 out of 5 average rating, 464 reviews

Quick and Easy Walk Downtown - Tons of Amenities

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

Top guest favorite

The living area features a cozy sofa, two reclining chairs, and elegant decor. A TV is positioned above a media console, while a dining area is visible in the background. Large windows allow natural light to fill the space, highlighting the light wood flooring.

Home in Sarasota

4.92 out of 5 average rating, 297 reviews

❤ Villa & Garden in Downtown ~ 5 Min to Beaches

Our bright and contemporary Heart Villa offers the quintessential Sarasota downtown and beach experience. It is nestled among tropical trees in a charming cul-de-sac in historic Laurel Park – right in the heart of downtown with loads of restaurants, boutiques, and sights on offer. Several fantastic beaches are just 5-mins ride away! And the villa's private garden is the perfect place to enjoy alfresco dining! We’ve poured our hearts & souls into this villa, it's our family business.

Top guest favorite

A covered front porch features two gray Adirondack chairs, set against light blue paneling. A welcoming door with a glass insert leads into the home. Planters with greenery add a touch of color amidst freshly mulched landscaping.

Home in Sarasota

4.97 out of 5 average rating, 102 reviews

"Chill Time” Great Location in Sarasota

Great location, only 1 mile from Downtown Sarasota. Cozy home with a mid-century flair in a quiet neighborhood near downtown Sarasota and minutes from Payne Park and the Legacy Trail. This is a family friendly home with a fenced back yard, close to all the great things Sarasota has to offer- museums, gardens, theaters, and beaches. The home is just a 1.5 miles to Downtown,15 min drive to Lido Beach, and 20 min to Siesta Key. One dog will considered with an added fee.

Top guest favorite

A charming outdoor patio area features a wooden pergola overhead, providing shade. Potted plants and herbs are arranged thoughtfully around the space. Two sets of double doors lead inside, complemented by white garden furniture, inviting relaxation and connection with nature.

Guesthouse in Sarasota

4.98 out of 5 average rating, 273 reviews

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area offers. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

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, 328 reviews

NEW 3/NTS JULY 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!

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Popular amenities for Saint Armands Key family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The image captures a shared pool area surrounded by lush greenery and palm trees. Lounge chairs with blue umbrellas are positioned around the pool, which is enclosed with a white fence. A pathway leads through well-maintained landscaping, enhancing the inviting outdoor space.

Condo in Sarasota

4.91 out of 5 average rating, 68 reviews

Steps from Lido Beach & St. Armands Circle

A large heated pool is surrounded by a spacious limestone deck, furnished with lounging chairs and tropical plant arrangements. Sunlight reflects off the clear water, creating a serene atmosphere. The pool area is designed for relaxation and enjoyment in a private outdoor setting.

Home in Siesta Key

4.97 out of 5 average rating, 29 reviews

Canal home short walk to Beach & Village, Heated P

Top guest favorite

An aerial view showcases a vibrant community surrounded by lush greenery. A swimming pool is visible alongside a hot tub and a mini putting green. Two tennis courts are situated nearby, and a tranquil pond complements the landscape.

Home in Sarasota

5 out of 5 average rating, 8 reviews

Private View Villa/Heated Pool/Pickleball/7883

Top guest favorite

A sandy pathway leads through lush greenery, providing access to a charming two-story building. The structure features a spacious balcony, surrounded by palm trees and local vegetation, under a bright blue sky with scattered clouds.

Apartment in Longboat Key

4.95 out of 5 average rating, 104 reviews

Longboat Key-OCEAN FRONT- on the beach

Top guest favorite

A spacious backyard is showcased, featuring a six-hole putting green with vibrant green turf. String lights are draped overhead, creating a warm ambiance against a pastel sunset sky. Outdoor seating areas and a solid fence provide privacy, enhancing the inviting outdoor environment.

Home in Sarasota

5 out of 5 average rating, 12 reviews

Putt 'n Plunge Paradise: 3/2 15 mins to Beach!

Top guest favorite

An open living area features tiled flooring and soft lighting, with comfortable seating arrangements including a sofa and armchairs. A dining area is visible, showcasing a wooden table with chairs. Decorative touches such as artwork and a side cabinet enhance the space's charm.

Cottage in Sarasota

4.99 out of 5 average rating, 92 reviews

Quaint Cottage,150 steps away from Crescent Beach!

A spacious outdoor area features a private saltwater pool with a sun shelf and adjoining heated spa. Lush landscaping and palm trees surround the pool, while a shaded patio with lounge chairs and an umbrella provides a relaxing retreat. The clear sky enhances the inviting atmosphere.

Home in Anna Maria

4.84 out of 5 average rating, 55 reviews

Crescent Palms north end AMI, 2 King suites

An aerial view captures the expansive Siesta Key coastline, showcasing a stretch of sandy beach meeting calm blue waters. Nearby buildings and lush greenery punctuate the landscape, highlighting the serene environment just minutes away from the cottages.

Cottage in Sarasota

4.77 out of 5 average rating, 135 reviews

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub

Family- and pet-friendly home rentals

The living area features light-colored sofas arranged around a central coffee table, with a decorative rug adding warmth to the space. Soft lighting from floor lamps complements natural light entering through a large frosted window. A mirror and wall art enhance the room's decor.

Home in Sarasota

4.89 out of 5 average rating, 134 reviews

Downtown Sarasota

A warm and welcoming room showcases a blend of natural wood paneling and vibrant artwork. Seating is provided by three bamboo stools, while a desk and lamp create an inviting workspace. A blue quilted bed and framed photos enhance the cozy atmosphere.

Home in Holmes Beach

4.97 out of 5 average rating, 137 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

An oversized private pool is surrounded by lush tropical plants and palm trees, offering a serene atmosphere. The pool features a gently curving shape and a tiled edge, with comfortable lounge chairs positioned nearby for relaxation.

Home in Bradenton

4.77 out of 5 average rating, 261 reviews

Tropical Paradise - Private Pool - Close Beaches

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 Sarasota

4.95 out of 5 average rating, 371 reviews

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

A neatly arranged sleeping area features a queen-sized adjustable bed dressed in a yellow quilt. A decorative bench with a grid pattern stands at the foot of the bed, and warm light emanates from a lamp beside the bed. A mirror and framed artwork add visual interest to the space.

Apartment in Sarasota

4.87 out of 5 average rating, 180 reviews

Hip Walkable District Water & Performance Theaters

Top guest favorite

A rectangular swimming pool is surrounded by a paved patio featuring a round table with four metal chairs. Potted plants with various greenery decorate the area, and a small structure is visible in the background under a clear blue sky.

Guesthouse in Sarasota

4.99 out of 5 average rating, 117 reviews

Sarasota Pool House

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

4.83 out of 5 average rating, 264 reviews

Private Siesta Beach House Oasis with Heated Pool.

A living room features two reclining genuine Italian leather couches arranged to face a wall-mounted 58" flat screen TV. Natural light enters through sheer curtains, highlighting the wood-burning fireplace and polished wooden flooring. A fan is centrally located above for ventilation.

Home in Sarasota

4.83 out of 5 average rating, 228 reviews

Home away from home mins to Siesta Beach! 4/2

Family-friendly home rentals with a pool

A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.

Condo in Siesta Key

4.85 out of 5 average rating, 176 reviews

Best Siesta Key Condo

The outdoor area showcases a heated saltwater pool surrounded by lounge chairs and a covered seating area. A manicured artificial turf putting green is prominently featured, providing a playful touch to the spacious backyard, which is framed by lush landscaping and bright skies.

Home in Bradenton

4.79 out of 5 average rating, 341 reviews

Heated saltwater pool home - turf putting green

A tranquil pool area is surrounded by lush greenery, with gentle palm trees swaying in the breeze. Lounge chairs are positioned alongside the clear blue water, while bright red umbrellas provide shade. Sunny skies add a bright atmosphere to the inviting scene.

Condo in Siesta Key

4.93 out of 5 average rating, 206 reviews

Steps away from beach and village! #1 in Siesta!

Top guest favorite

A comfortable living area features a neutral sofa with decorative cushions, flanked by two bedside tables with lamps. A piece of wall art depicting a beach scene adds a calming touch, while a ceiling fan provides overhead cooling. Natural light is visible through an open doorway.

Condo in Siesta Key

4.92 out of 5 average rating, 243 reviews

Sea Club 2 - Relaxing Siesta Key Beach Condo-Siest

Top guest favorite

A serene community pool is surrounded by a fence and complemented by lounge chairs positioned nearby. The pool's clear blue water reflects the sunlight, while the yellow exterior of the building provides a warm backdrop. Windows with awnings complete the inviting atmosphere of the area.

Apartment in Sarasota

4.94 out of 5 average rating, 154 reviews

Super Clean! 2/2 condo Walk to SKey!

A spacious saltwater pool is surrounded by lounge chairs on a paver deck. Palm trees offer shade in the background, and a bright blue sky is overhead. The multi-story building can be seen in the distance, providing a backdrop to the leisure space.

Cottage in Sarasota

4.73 out of 5 average rating, 153 reviews

Drift Inn A Heated Pool & Private Beach Access!

Top guest favorite

A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.

Home in Anna Maria

4.94 out of 5 average rating, 179 reviews

Discounted 20% - Two open August weeks w/Dock-Pool

A single-story home is depicted, featuring a light-colored facade and a two-car garage. Lush green grass surrounds the property, with palm trees partially framing the view. The sky is filled with fluffy clouds, enhancing the welcoming appearance of the residence.

Home in Sarasota

4.86 out of 5 average rating, 170 reviews

The Sea is Calling

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