Family-friendly holiday rentals in Sarasota

Sarasota Retreat/Beaches/Pool/8.5mi. to Siesta Key

Welcome to your Sarasota retreat!! Enjoy a private heated pool home just 8.5 miles from the white sands of Siesta Key. With multiple bedrooms and an additional living room/lania, there’s plenty of space to spread out and relax. Start your mornings with coffee poolside, spend beach days exploring the coast and downtown dining, then unwind in comfort... Perfect for: • Families wanting space and a private pool • Couples looking for a warm-weather getaway Your perfect Florida vacation starts here...

[The Bay St. Hideaway]Private Swimming Pool& Patio

Welcome to Bay Street Hideaway VR24-00156 A beautiful home to make your next family vacation the best one yet! The whole group will enjoy easy access to everything from this centrally located place. The patio fenced in backyard with a private HEATED pool provides a quiet and peaceful area if you want to avoid the crowds.The house is a 2 story completely furnished with 4 bedrooms and 3.5 bathrooms. TV's are provided in the living room, a few bedrooms, and lounge area upstairs. 3 E-bikes included

Coastal Farmhouse - 3/2 with heated saltwater pool

Experience relaxation at this tranquil 3BD/2BA home with a heated pool, perfect for a family retreat! Prepare meals in the fully equipped kitchen or savor local delights on the screened-in lanai. Each bedroom boasts plush bedding, ensuring a restful night's sleep. Plus, a cozy living room. Conveniently located, just under 9 miles from Siesta & Lido Key Beach, Der Dutchman 2.2 miles and 2.5 miles from Yoder's Restaurant. Shopping and dining options at University Town Center, only 7.7 miles away.

Luxury 3B/3B waterfront home w/ pool + boat access

Escape to this luxurious 3BR/3BA Sarasota sanctuary! 5 minutes from Siesta Key, this Mid-Century Modern gem sits on a canal with direct Bay access (no bridges). Dive into the private pool & spa, lounge on the 1,000 sq ft porch, or relax inside on cozy furnishings. Includes a private dock, kayak/SUP/canoe, bikes, and a massive driveway for boat trailers. From the hanging bed swing to the gourmet kitchen, every detail is designed for your dream waterfront getaway. Your Florida paradise awaits!

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. *Brand new pool* VR24-00265

Sapphire Shores Muse | 2 Bed 3 Bath | Luxe Pool

Welcome to Sapphire Shores Muse, a stylish, fully-furnished retreat perfect for 30+ day stays. Located minutes from Siesta Key and downtown Sarasota, this upscale home offers a private pool, shaded lounge, and outdoor dining—ideal for unwinding after work. Inside, enjoy a chef’s kitchen, smart TVs, fast Wi-Fi, and serene bedrooms with luxe linens. Perfect for corporate stays, traveling nurses, snowbirds, local renovations and relocations. Experience Sarasota in comfort and style—book now!

The Blessing House- Htd Pool/Spa, Close to Beaches

Welcome to The Blessing House, a beautifully curated Sarasota retreat designed for relaxation, comfort, inspiration, and quality time together. Enjoy a heated pool & spa, lush lanai, bright designer interiors, and a peaceful residential setting just 15 minutes from Siesta Key, Lido Key, and downtown Sarasota. Thoughtfully maintained and enjoyed by our family throughout the year, this home is ideal for couples, families, and discerning travelers seeking a restful and memorable getaway.

Resort Style Retreat, Pickleball, Htd Pool, Play.

- FREE POOL HEAT, private pool - PICKLEBALL COURT in our back yard. - 2 King Beds, Queen sleeper sofa, 2 bunk beds - Close to Anna Maria Island - 7.3 miles to IMG Academy - Large back yard fully fenced - BBQ Grill - Outdoor TV - Corn toss - Ping Pong - Boardgames - Outdoor dining table - 1 mile from Robinson Preserve: kayak rentals, nature hiking, running, and playgrounds - Beach chairs, beach towels, cooler, umbrella provided. - pack n play, high chair - Smart TV in every room

Mid-Century Oasis with Pool in Arlington Park 1

A perfect blend of Sarasota’s architectural heritage and contemporary elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath & pull out sofa in a mid-century gem offers a serene escape, providing a refreshing interplay of historical charm and modern luxury. Enjoy the separate sunroom/office for those working from home, or use as an extra sleeping space with comfy pull out sofa. Take a break with a quick dip in the sparkling pool. VR24-00160

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

Welcome to Palm Noir, a brand-new modern luxury retreat in Sarasota just 12 minutes from Siesta Key Beach and 9 minutes from Downtown. This stunning pool home features soaring ceilings, impact windows and doors, designer finishes, luxury furnishings, bright open living spaces, and a private heated pool with spa. Enjoy premium bedding, fresh towels, a fully equipped kitchen, outdoor dining, lounge seating, and everything needed for the perfect family vacation or group getaway.

Sea Esta | Private Saltwater POOL + Putting Green!

BNB Breeze Presents: Sea Esta! Experience this stunning home in the heart of Sarasota, located just 10 minutes away from Siesta Key Beach! From the gorgeous interior, to the INCREDIBLE outdoor oasis, this home has it all! • Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st • Resort-Like Back Yard w/ a Pergola, Turf + Putting Green + Bikes • Pool + Beach Supplies • Fun Outdoor Swinging Dining Table

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 has to offer. 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.