Holiday rentals with a pool in South Sarasota

The Wisteria Oasis W/swings, heated pool & hot tub

A Florida wellness retreat>>> Discover the charm of our delightful cottage, exceptionally placed amidst lush greenery! The interior offers an inviting ambiance with its plush, comfortable furnishings and a well-equipped kitchen with an espresso machine. Quietly nestled away from the hubbub of city life, our cottage offers a tranquil escape yet is in close to local attractions. Relish the day exploring charming seaside villages and beaches or simply bask in the serenity of your private haven.

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

Tropical Oasis Heated Pool Hot Tub Near Siesta Key

Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!

Beautifully Remodeled Home with Pool Near Siesta

It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

Beach & Town Posh Location! Jungle Paradise Studio

PRIME! To Town&Beach Locations! *Private Studio* *NO Smoking *NO Children. *Shared Pool. Studio w/private entrance & patio @Designers private Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Beach, shops, dining, & 5mins/Downtown Sarasota. Walk/local markets/ dining/movies & shopping New King bed. New 50" TV. Off street parking. No Smoking/Vaping! No kitchen. No Hotels in my exclusive area! Live like a local!

The Sand Castle - Backyard Oasis Mins from Siesta!

*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want!

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

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

Family-Friendly 3BR Home w/ Private Heated Pool, Hot Tub & Backyard– Near Siesta Key! Located just minutes from world-famous beaches, and a wide variety of dining, shopping, and entertainment options, this home is the perfect base for your Sarasota vacation. Whether you’re planning a family trip, a couples’ retreat, or a friends’ getaway, you’ll love the blend of comfort, convenience, and fun!

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. 🌴

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!

Lake View 1BR Condo | Heated Pool Near Siesta

Bright 1-bedroom condo with peaceful lake views in a quiet residential area of Sarasota. Siesta Key Beach is a 5–10 minute drive (traffic dependent). Pet-friendly home — all pets welcome with a flat $10 pet fee per reservation, regardless of the number of pets. Guests enjoy access to a heated community pool and a calm setting close to shopping and dining.

Private Siesta Beach House Oasis with Heated Pool.

Come enjoy the #1 rated beach in the USA. A contemporary style beach house that is located in a very conveniently located 10 min from Siesta Key beach. Within .5 miles you will find a mall, Cinebistro, trendy local bars, all major banks, Trader Joe’s, Publix, and a gas station. Drive way accommodates 2 cars with street parking as well.