Vacation rentals with a pool in Saint Armands Key

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Top-rated rentals with a pool in Saint Armands Key

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious living area features a light-colored sofa and armchairs, with decorative pillows adding color. A coffee table sits in the middle, and a flat-screen TV is mounted on the wall. Natural light streams through windows, complementing the neutral-toned decor and beach-themed accents.
Condo in Sarasota
4.96 out of 5 average rating, 26 reviews

Lido Beach/St. Armands Condo

You won't believe it until you see it! 3 min. walk to Lido Beach, 30 seconds to the hundreds of shops and restaurants of St. Armand's Circle, 10 min. drive to airport. This condo is SO BRIGHT & is equipped with everything you need for your beach vacation. Enjoy wifi, cable TV, smart TV's, beach chairs & umbrella, screened-in porch, washer/dryer IN UNIT (also access to the community laundry if desired). Free trolley to take you to downtown SRQ. Parking Spot. Too much fun at your fingertips!

Superhost
Home in Sarasota
5 out of 5 average rating, 5 reviews

Coconut Cottage | Walk to Lido Beach & St. Armands

🦩 Exclusive Amenities Include • Private Heated Pool & Spa • Outdoor Lounge Area with TV, Exterior Heaters, Fire Table , Dinning Area, & Ping Pong Table • Less than a 2 minute walk to St. Armands Circle • Less than a 6 minute walk to Lido Key Beach • 4 Bedrooms, 3 1/2 Bathrooms • 2 King Beds, 2 Queen Beds, & 1 Twin Roll Away Bed (Sleeps 9) • Water Filtration System Added • Free WiFi & 4 Smart HDTV’s with Cable • Beach Towels, Chairs, Cooler, & Caddy Provided • 4 Bikes & 2 Kayaks with Life Vests

Top guest favorite
Apartment in Sarasota
4.93 out of 5 average rating, 122 reviews

2 BR Beachy Speakeasy | Rooftop Deck | Lido Beach

Picture this: a rooftop deck, just a 7 minute walk to the pristine sand of Lido Beach, and surrounded by the charm St Armand's Circle with boutiques, and eateries, all within a short walking distance. Forget the conventional - this condo's got a secret. Tucked behind an unassuming door, a unique rear retail/service entrance near dumpsters; a second-floor walk-up, no elevator, lies a vibrant space, drawing inspiration from speakeasy culture fused w/ a beach vibe. Your adventure starts now

Top guest favorite
A serene beach scene highlights soft white sand stretching along the coastline. Calm turquoise waters gently lap at the shore under a clear blue sky. Beach loungers and umbrellas are positioned along the sand, with a natural backdrop of greenery in the distance.
Apartment in Longboat Key
5 out of 5 average rating, 107 reviews

Sandy Toes: Open July 26th - 31st!

This sublime oceanfront studio condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the ground floor, overlooking the heated pool and ocean, this dreamy studio 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 distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.
Home in Sarasota
4.95 out of 5 average rating, 242 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

Superhost
Home in Sarasota
4.63 out of 5 average rating, 8 reviews

Beautiful Historic Ringling house!

Welcome to the John Ringling House, a three-bedroom and two-bathroom one-of-a-kind masterpiece on the National Historic Registry and is a 1924 Historic John Ringling Estate. Located in the prestigious John Ringling Estates neighborhood, this home is a quick stroll to St. Armands Circle, known for premier shopping and luxury dining, and is near the award-winning Gulf of Mexico Beaches. Immerse yourself in the island's rich history while enjoying a luxury vacation!

Guest favorite
A private pool is surrounded by a tiled patio featuring lounge chairs. Lush greenery provides privacy, while kayaks are stored against the wall. The structure above includes a staircase leading to the upper level, complementing the outdoor space.
Home in Sarasota
4.87 out of 5 average rating, 101 reviews

Lido Key House

One story house with two bedrooms and two bathrooms located one block from Lido Beach and a short walk from the stores and restaurants of St. Armand's Circle. It features an open, airy interior, large patio and newly constructed private pool and a recently updated kitchen. (Property also has a studio apartment that is unoccupied and does not have access to the grounds or pool.) City certificate of reg. #VR22-00012

Top guest favorite
Home in Sarasota
4.98 out of 5 average rating, 117 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

Top 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
4.98 out of 5 average rating, 362 reviews

JULY AVAIL! Sarasota #1 Luxury Villa w/PRIV BEACH!

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!

Superhost
Cottage in Sarasota
New place to stay

Modern Lido Key Cottage Pool & Steps to Beach

NEW LISTING Discover a calm, stylish coastal studio apartment, perfect for couples or solo adventurers seeking a serene escape. This bright space features a well-equipped kitchen, walk-in shower, and access to a vibrant community pool. Enjoy beach-ready amenities like chairs, a cooler, and a wagon. Comfortably fits 2 guests in the queen-sized bed.

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

Family Getaway • Heated Pool• 17 min Beach•PacMan

Welcome to ☀️ Vista Del Sol ☀️! This family-friendly Sarasota home is a Guest Favorite for good reason — heated pool, Pac-Man arcade, shuffleboard, EV charger, and everything your family needs for a perfect Florida getaway. 🌴

Guest favorite
An aerial view of Siesta Key displays a coastal neighborhood with a network of waterways. The vibrant blue water contrasts with the greenery and residential homes, highlighting the island's tranquil setting. The city skyline of Sarasota is visible in the distance, framing the picturesque scene.
Home in Sarasota
4.99 out of 5 average rating, 103 reviews

Siesta Key Beach Getaway

Two bedroom, two bath, 2000 sq. ft. single-family home accommodates up to 4 on the beautiful island of Siesta Key just off North Bridge with quick access to the number one beach in the U.S. and Sarasota nightlife!

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