Holiday rentals with a pool in Saint Armands Key

Find and book unique homes with a pool on Airbnb

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.

1 of 1 pages1 / 1
Top Guest favourite
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, 25 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 favourite
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 favourite
Condo in Longboat Key
4.98 out of 5 average rating, 241 reviews

Island Time: Open July 7 - 10!

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...!

Superhost
Home in Sarasota
4.57 out of 5 average rating, 7 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!

Top Guest favourite
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, 382 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.

Top Guest favourite
Home in Sarasota
4.98 out of 5 average rating, 116 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 favourite
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, 361 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!

Guest favourite
A serene private pool is showcased with a gentle waterfall feature, surrounded by lush tropical foliage. Vibrant green leaves and purple flowers frame the pool, creating a tranquil retreat. The clear water reflects the soothing sounds of the cascading water, enhancing the outdoor ambiance.
Home in Sarasota
5 out of 5 average rating, 11 reviews

Walk to Lido Beach/St Armands, HEATED pool w/grill

VR22-00146 - Walk to Lido Beach/ St. Armands, HEATED POOL 3 BR home w/grill, privacy, walk to shopping and restaurants!! This home is a piece of paradise! One block to the beach, 5-minute walk to St. Armands! What else makes this property unique? Not only do you have an amazing private pool, but it's also heated! Walk to everything that Lido has to offer!

Top Guest favourite
Home in Sarasota
5 out of 5 average rating, 21 reviews

Luxury Lido Key Heated Pool & Game Room

Escape to a beautiful, tropical oasis on Lido Key. This renovated home features a heated saltwater pool, fire pit, and a full game room. Perfect for families and groups, it's just steps from St. Armand's Circle and the beach. Enjoy seamless indoor-outdoor living in a lush, fully fenced backyard. Your ultimate Florida getaway awaits!

Guest favourite
A mid-century structure is set among lush palm trees, showcasing a combination of wooden accents and large glass windows. A curved gravel driveway leads to the front entrance, inviting natural light into the living areas and offering a serene outdoor landscape.
Home in Sarasota
4.92 out of 5 average rating, 147 reviews

St Armand's Mid-Century Oasis

Mid-century retreat in the heart of Lido Key! Stroll to pristine beaches or enjoy the vibrant shops & eateries of St. Armand's Circle just steps away! Recently renovated with authentic period details, this 3BR/3BA gem boasts a sparkling pool, sun-soaked rooftop deck and stylish office. VR2400013

Guest favourite
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!

Popular amenities for Saint Armands Key rentals with a pool

Destinations to explore