Family-friendly vacation rentals in Siesta Key

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Siesta Key

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

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Top guest favorite
Home in Siesta Key
4.91 out of 5 average rating, 127 reviews

Siesta Key, FL - Casa Berano

Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beaches 7 days/wk. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets max (dogs only), under 50lbs.

Guest favorite
A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.
Home in South Sarasota
4.98 out of 5 average rating, 137 reviews

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

Guest favorite
Condo in Siesta Key
4.79 out of 5 average rating, 105 reviews

Beachwalk Townhouse with view of Gulf of Mexico

Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

Top guest favorite
An airy dining area features a glass table supported by a unique wooden base, surrounded by four woven chairs. Natural light floods the open space, highlighting the modern kitchen with white cabinetry and high-end finishes, while a large pendant light adds a stylish touch.
Home in Siesta Key
4.99 out of 5 average rating, 100 reviews

Private Standalone Home - Walk to Siesta Key Beach

Welcome to your private escape on Siesta Key, an ideal retreat for a relaxing vacation. This renovated, standalone single-level home is tucked away on a quiet, tree-lined street, offering rare privacy just a short walk from Siesta Key’s famous white-sand beaches, restaurants, and bars. Surrounded by lush tropical gardens, enjoy peaceful seclusion plus access to a large heated community pool and an intracoastal pier, perfect for morning coffee, afternoon fishing, or sunset tropical drinks.

Top guest favorite
Condo in Longboat Key
4.98 out of 5 average rating, 241 reviews

Island Time!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Top guest favorite
A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.
Home in Holmes Beach
4.97 out of 5 average rating, 105 reviews

Salty Harbor AMI pool retreat near the Beach

Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our calendar! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

Guest favorite
Home in Sarasota
4.93 out of 5 average rating, 397 reviews

Heated&Renovated Pool•Beach Retreat•15m to Siesta

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

Guest favorite
Home in Sarasota
4.98 out of 5 average rating, 113 reviews

Pool, Shuffleboard, EV charg, Near beach, UTC mall

Welcome to Vistalodgings Vista Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀  Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

Top guest favorite
Home in Sarasota
4.95 out of 5 average rating, 192 reviews

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. VR24-00265

Top guest favorite
A single-story tropical home is presented with a light blue exterior and a metal roof. Lush palm trees and colorful plants border the pathway leading to the entrance. An outdoor umbrella sits near the entry, enhancing the welcoming appearance of the property.
Home in Siesta Key
4.93 out of 5 average rating, 161 reviews

Siesta Key Beach & Village 2BR/2BA Steps to Beach

This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located in the heart of Siesta Key Village. You will be within a 2 minute walk to Siesta Key Beach and Siesta Village. With a beach house décor and equipped with 3 smart TVs, WIFI, cable, refrigerator, microwave, W/D, grill, beach chairs, toys for the kids, beach wagon, 1 queen bed, 2 twin beds and sleeper queen sofa. This private beach home has everything you need for a beach vacation. Local ownership.

Guest favorite
Home in Siesta Key
4.85 out of 5 average rating, 117 reviews

Stylish & Bright: Steps to Beach ~ Pool ~ Hot Tub!

Stay at a vibrant 2BR beachfront duplex in the heart of Siesta Key—just steps from the sand, dining and local attractions. This colorful retreat blends modern comfort with fun outdoor living, featuring a private cabana with hot tub and a shared pool. Perfect for couples, families and beach lovers. ☀ Shared pool ☀ Steps to the beach ☀ Pet-friendly ☀ BBQ area ☀ Private hot tub ☀ Pets allowed ☀ Wifi & Free parking Your perfect seaside escape awaits!

Top guest favorite
A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.
Condo in Siesta Key
4.97 out of 5 average rating, 381 reviews

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.

Popular amenities for Siesta Key family-friendly rentals

When is the best time to visit Siesta Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$66,733 GYDG$83,468 GYDG$90,999 GYDG$72,381 GYDG$57,110 GYDG$56,273 GYDG$56,901 GYDG$51,671 GYDG$46,441 GYDG$49,370 GYDG$57,319 GYDG$61,921 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

Quick stats about vacation rentals that are family-friendly in Siesta Key

  • Total vacation rentals

    Explore 1,860 vacation rentals in Siesta Key

  • Nightly prices starting at

    Siesta Key vacation rentals start at G$12,552 GYD per night before taxes and fees

  • Verified guest reviews

    Over 25,570 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 350 rentals that welcome pets

  • Vacation rentals with a pool

    1,530 properties feature pools

  • Rentals with dedicated workspaces

    870 properties have a dedicated workspace

  • Wi-Fi availability

    1,810 of Siesta Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Siesta Key rentals

  • 4.8 Average rating

    Siesta Key stays are highly rated by guests—averaging 4.8 out of 5!

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