Holiday rentals with a pool in Saint Armands Key

Mid-Century Oasis with Pool in Arlington Park

Classic elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath 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. Take a break with a dip in the sparkling pool or a game of Bocce ball in the backyard. Walk to Southside Village, Arlington Park pool/tennis/basketball/rec/playground, minutes from downtown & the bay. Boat Parking VR-2400161

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!

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

Beach Bliss: Discounted August & September!

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...!

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.

Mermaids Oasis | Walk to St. Armands Circle, Pool

🦩Exclusive Amenities Include: • Private Heated Pool & Hot Tub • 5 Minute Walk to St. Armands Circle • 10 Minute Walk to Lido Key Beach • 3 Bedrooms, 3 Full Bathrooms & 1 Half Bath • 2 King Beds, 1 Queen Bed & 2 Futons • Screened-In Lanai w/ Outdoor Lounging Space • Outdoor Dining Area • Gourmet Kitchen • Dry Bar w/ Wine Refrigerator • 2 Kayaks, 4 Bikes • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, Kitchen Essentials Provided • Gas Grill

Steps from Lido Beach & St. Armands Circle

Come getaway and enjoy yourself along with your loved ones or just for a private relaxing break from it all. This One Bedroom/One Bath apartment w/ Lanai(Screened Balcony), and shared Pool/Jacuzzi is located steps from the beautiful Lido Beach, boutique shopping, spa's and incredible dining on St. Armands Circle. If your looking to have everything you need from world famous beaches to historical sites and great food around the corner come and stay!

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

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. 🌴

DEC SALE! 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!

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!

Kingston Arms 8A by FVC

Renovated 2brm ground floor with easy walk to St. Armands Circle for dining and shopping as well as to Lido Beach. Or stay and enjoy the large community pool!