Holiday rentals in The Meadows

4.98 out of 5 average rating, 104 reviews

A cozy living area features a light blue wall, with a comfortable white sofa arranged around a neutral-toned rug. In the foreground, a wooden dining table with four chairs provides seating. Natural light enters through a doorway that leads to an outdoor space.

Guest house in Bradenton

Serenity Lake

Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

5.0 out of 5 average rating, 12 reviews

The exterior of a modern two-story condo building is displayed, featuring light blue siding and white accents. Paved pathways lead to individual garages, bordered by neatly manicured landscaping. A clear sky with a few clouds is visible above, enhancing the bright and inviting appearance of the area.

Townhouse in Sarasota

Summer getaway near Siesta Key: Family Getaway

Discover your family getaway at this stylish 2-bedroom, 2.5-bath condo in the heart of Sarasota. Perfectly located just minutes from beautiful beaches, shopping, and dining, this modern home offers a serene atmosphere for relaxation. Enjoy a fully equipped kitchen, cozy living space, and all the essential amenities for a comfortable stay. Ideal for families seeking both tranquility and convenience, your oasis at Sienna Park awaits. Book now and create unforgettable memories in sunny Sarasota!

A covered patio area features modern wicker furniture with white cushions, positioned around a glass coffee table. The inviting space overlooks a pristine pool, surrounded by a protective screen. Lush greenery is visible in the background, enhancing the tranquil setting.

4.96 out of 5 average rating, 154 reviews

Luxury Pool Family Oasis-Siesta Key/DT 3BR/2BA

Welcome to your home away from home! This renovated, spacious, and bright pool home will immerse you in a luxurious experience the minute you arrive. Located on a lush, quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in the USA), 10 minutes to downtown (with fantastic restaurants and shopping), and within walking distance of the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake Park, and the new UTC mall!

4.95 out of 5 average rating, 199 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. *Brand new pool* VR24-00265

4.95 out of 5 average rating, 63 reviews

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

Home in Arlington Park

Private Heated Pool Retreat for Two Families

🌴 Welcome to your private Sarasota escape - designed for easy, extended stays, where two families can relax together around a private heated pool. With generous living spaces and thoughtful touches throughout, the home balances comfort and connection. Located minutes from Siesta Key, Lido Beach, and downtown Sarasota, and within walking distance of a park with playground, public pool, courts, fitness areas, and scenic trails. Relaxed, comfortable, and ideal for memorable family getaways.

A spacious seating area features comfortable chairs surrounding a modern fire table. A clear view of the salt water heated pool is available through large glass doors. Outdoor furniture is positioned beside the pool, with lush greenery visible in the background.

4.98 out of 5 average rating, 58 reviews

Sunshine House- Sarasota Pool Retreat

Welcome to the Sunshine House, a sunny Sarasota retreat in a quiet neighborhood! This 3BR/2BA home has a saltwater heated pool, fully equipped kitchen, spacious living area and an office setup with super fast WiFi and an extra monitor. Pet friendly with a fully fenced yard. We stock beach chairs, loungers, umbrellas, towels, bags and toys, plus 4 bikes (one recumbent). Lido Beach is 7 miles away, Siesta Key 10. Downtown dining and shopping are minutes out. Your perfect getaway awaits!

4.94 out of 5 average rating, 317 reviews

MG Tropical Stay. Fully private, no shared spaces

Welcome to your modern Sarasota Guest Suite – Adults Only, Private & Peaceful 🌞 Remodeled on January 26, 2026, this private suite offers a separate entrance and parking for two cars. Enjoy a cozy queen bed, full bathroom, and a kitchenette with microwave, mini‑fridge, coffee maker, and more. Relax on your private patio with a solar shower. Stay cool with a quiet mini‑split A/C. We provide beach essentials: umbrella, chairs, cooler, and towels—perfect for your Sarasota beach days 🌴

The studio apartment features a spacious bed with light-colored linens, complemented by two decorative pillows. A sleek brown sofa is positioned in front, adorned with a soft throw blanket. Natural light enters through the window, enhancing the clean and modern design.

4.82 out of 5 average rating, 246 reviews

Comfortable + Functional Private Studio Apartment

This comfortable, clean, and private studio apartment is the perfect spot to relax- whether you're here on business or you've spent the whole day on the beach! Recently remodeled with a dining table to take your meals, hot water, a comfortable bed, and refreshment center, you will be lacking nothing here! This apartment is a guest suite attached to the main living area of the home and is completely private, however there is a resident who lives in the main part of the home.

5.0 out of 5 average rating, 107 reviews

A charming house with a well-manicured lawn is framed by lush greenery. The front porch is accented by decorative red doors, and a stone walkway leads up to the entrance. Large trees provide shade over the landscaped yard.

Home in Bradenton

Peaceful Braden River Oasis: Main House

Escape to our charming riverfront Main House—a spacious 2 bed, 2 bath retreat that sleeps up to 7. Enjoy stunning river views, a screened-in porch, and access to the peaceful river dock. With a master suite featuring an outdoor shower and a spacious lofted sleeping area, this home offers everything you need for a relaxing and memorable getaway. Part of a unique property with two other rental units—perfect for groups or families seeking tranquility and adventure.

Superhost

Flat in The Meadows

Beautiful Condo with golf view

Turnkey furnished condo 2 bed/2 bath w/FABULOUS GOLF COURSE & LAKE VIEW. Close to dining, shopping, entertainment, downtown Sarasota & beautiful beaches. Lovely tile floors. Designed and furnished w/your comfort in mind. You will truly enjoy your vacation in paradise. The heated Community pool is across the street. HIGH SEASON = DEC–APR: $4,500/m LOW SEASON = MAY–NOV: $2,800/m In High season, a 3 month minimum stay is required. NO Smoking.

5.0 out of 5 average rating, 4 reviews

A caged outdoor space features a heated saltwater pool, surrounded by a spacious deck. Sun loungers are positioned nearby, and a covered area for dining is visible in the background. Lush greenery adds a touch of nature to the setting.

4.87 out of 5 average rating, 195 reviews

Beaches, Shopping, Sculling-Sarasota is calling!

Escape to this 3BR, 2BA Sarasota retreat in a quiet neighborhood, just minutes from UTC Mall, Nathan Benderson Park, and a short drive to award-winning beaches. Sleeps 6 comfortably with a bright open layout, fully equipped kitchen, and cozy living spaces. The highlight is the private heated saltwater pool, perfect for relaxing after a day of shopping, dining, or beach adventures. Your Sarasota getaway starts here!

A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.

5.0 out of 5 average rating, 110 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

Popular amenities for The Meadows holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in The Meadows

5.0 out of 5 average rating, 18 reviews

Good Vibrations Home

4.87 out of 5 average rating, 90 reviews

YC Tropical stay. 100% Private & 2 parking spots.

4.9 out of 5 average rating, 51 reviews

Private Jacuzzi & Mini Golf Near Beaches

A spacious studio features light-colored walls and wood-style flooring. A Queen bed is positioned centrally, accompanied by two bedside lamps. A small desk and chair are placed nearby, with a door leading to a bathroom visible in the background. Natural light filters through nearby curtains.

4.88 out of 5 average rating, 73 reviews

Private Studio Getaway in Sarasota!

4.97 out of 5 average rating, 34 reviews

The Seapearl - 1/1 Guest Suite

A light-filled living area features a bay window with multiple panes and a ceiling fan. A comfortable gray sofa is paired with a patterned rug, and a small coffee table sits atop it. Two armchairs provide additional seating, while a plant adds a touch of greenery.

4.91 out of 5 average rating, 22 reviews

Little Yellow Cottage

4.91 out of 5 average rating, 45 reviews

Shangri La