Vacation rentals with a pool in Southgate

4.97 out of 5 average rating, 130 reviews

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.

A living area features wooden flooring with a large area rug at the center. Two gray armchairs are positioned near a media console, which supports a flat-screen television. Natural light is provided by windows adorned with sheer white curtains, and a green plant adds a touch of greenery.

4.95 out of 5 average rating, 537 reviews

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

The outdoor area features a uniquely shaped heated saltwater pool with clear blue water. Surrounding the pool are loungers placed on a bright, white deck, complemented by tropical plants and palm trees that enhance the tranquil environment.

4.98 out of 5 average rating, 121 reviews

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!

A private backyard oasis is highlighted by a heated pool and a hot tub, surrounded by lush tropical landscaping. A shaded area with an umbrella and seating for outdoor dining is visible beside the pool, creating a serene environment for relaxation.

4.97 out of 5 average rating, 128 reviews

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

Welcome to Siesta Fiesta, where dreams of relaxation become reality. With the backyard heated pool and hot tub, you have your own oasis to channel inner peace. If you’re feeling froggy, hop over to the beaches, take a kayak tour through the mangroves, a beautiful chartered sunset cruise, or try some of the local eateries that guests rave about! Whether you want to stay in, or go out, this home offers you everything you could need or want and will satisfy for pure relaxation or adventure!

A sparkling pool is surrounded by a spacious patio, featuring lounge chairs and a vibrant red umbrella. Lush tropical landscaping creates a serene retreat, providing an inviting space for relaxation and leisure under a clear blue sky dotted with fluffy white clouds.

4.96 out of 5 average rating, 157 reviews

Mid-Century Oasis with Pool in Arlington Park 1

A perfect blend of Sarasota’s architectural heritage and contemporary elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath & pull out sofa in a 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, or use as an extra sleeping space with comfy pull out sofa. Take a break with a quick dip in the sparkling pool. VR24-00160

5 out of 5 average rating, 106 reviews

The Blessing House- Htd Pool/Spa, Close to Beaches

Welcome to The Blessing House! This home has been beautifully renovated, designed & curated for you to be rejuvenated, relaxed & inspired during your stay. You will love the heated pool & spa, the spacious lanai with plant wall, the fresh and bright design, and the amazing location of this house. The Blessing House is only a 15 min drive to Lido Key Beach & Siesta Key Beach, tons of shops & restaurants and the lovely Arlington Park is only about a 7-10 min walk away.

Superhost

A heated pool is framed by lounge chairs, with lush tropical plants surrounding the area. The back of the home features large glass doors, providing a view into the inviting living space. A subtle sunset sky adds a soft glow to the scene.

4.77 out of 5 average rating, 145 reviews

"Charming Pool Home 1 Mile from Siesta Key"

Your Sarasota Sanctuary Awaits 🌴 Newly refurbished 3BR/2BA pool home minutes from Siesta Key Beach, dining & boutiques. Featuring designer furnishings, a gourmet kitchen, and bright open spaces. Relax by the private heated pool (baby fence on request), enjoy central AC & ceiling fans. Sleeps 8 guests max. with hypoallergenic bedding (king, queen, full, plus an additional premium airbed). Peaceful, quiet neighborhood. 🚭 No smoking/pets/parties. 🚗 Parking for 3.

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.94 out of 5 average rating, 127 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

4.92 out of 5 average rating, 359 reviews

A private caged pool area is surrounded by lush tropical greenery. A turquoise umbrella provides shade over a lounge chair, while a series of blue-tiled steps lead into the pool. Potted roses add a touch of color beside the water.

Guest suite in Sarasota

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!

A person is seated at the edge of a sparkling pool, facing the clear blue water. The poolside is tiled, and the sunlight reflects off the surface, creating a serene ambiance. The individual wears a swimsuit featuring a tiger stripe pattern.

4.95 out of 5 average rating, 131 reviews

Luxury Pool Family Home-Siesta Beach/DT-3BR/2BA

Welcome to your private oasis! This stunning pool home has undergone a meticulous renovation, offering a spacious and luminous retreat. Nestled on a serene street, it provides a peaceful escape while being in close proximity to Sarasota's top destinations. Whether you're seeking the sun-kissed shores of Siesta Key Beach, the vibrant downtown scene, or the flavors of the Fresh Fish Waltz Market, this home offers easy access to it all.

4.94 out of 5 average rating, 111 reviews

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

4.98 out of 5 average rating, 112 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. 🌴

Popular amenities for Southgate rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private pool area is showcased within a screened enclosure, featuring clear waters and sun loungers. Colorful umbrellas in red and green provide shade, while tall palm plants are arranged around the space. The adjacent home showcases large windows, offering views of the inviting outdoor area.

5 out of 5 average rating, 16 reviews

Sarasota's Luxury Oasis

5 out of 5 average rating, 12 reviews

Siesta Key 3BR w/ Heated Pool, Game Room & Lanai

Superhost

A modern outdoor space features a private heated pool surrounded by lounge chairs. The white pool deck is complemented by lush greenery. A separate dining area is visible on the second level balcony, offering a serene view of the backyard oasis.

5 out of 5 average rating, 15 reviews

The Palace on Clematis – Luxury Siesta Key Retreat

A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.

4.95 out of 5 average rating, 156 reviews

Beautifully Remodeled Home with Pool Near Siesta

A welcoming living area features a light-colored sectional sofa, a wooden coffee table, and various decorative elements. Soft beige carpet covers the floor, while a tropical plant adds a touch of greenery. Light flows through a large window, illuminating the space.

4.94 out of 5 average rating, 50 reviews

Golden Breeze Pool House

A private solar-heated pool is framed by a spacious patio featuring terracotta tiles. Colorful lounge chairs are arranged beside the pool, and glass doors lead into the living area. A shaded seating area offers comfort under the overhang, enhancing the outdoor space.

4.81 out of 5 average rating, 91 reviews

Best Location, Clean,w/ Fenced Yard & Private Pool

An open living area features a light-colored seating arrangement, including two armchairs and a sofa, with a wooden coffee table at the center. A wall-mounted TV is visible, and a dining area with a table and chairs is located nearby. Natural light enters through sliding glass doors.

5 out of 5 average rating, 41 reviews

Cozy Getaway Home near Siesta Key Beach

A serene saltwater pool features a spa section, adorned with colorful inflatable floats. Lush greenery surrounds the pool area, enhancing the tranquil outdoor space, with a clean, modern stone deck complementing the vibrant tile accents.

5 out of 5 average rating, 96 reviews

Modern Organic King Beds Salt POOL/SPA SRQ Escape

Condo rentals with a pool

4.96 out of 5 average rating, 218 reviews

A serene lanai view features a dining table with chairs overlooking the community pool. Lush palm trees frame the scene, while sunlight reflects off the water's surface. A doorway is visible, leading to the interior of the condo.

Condo in Sarasota

Gateway to Siesta Key - 1/2 Mile to the Beach

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.

4.97 out of 5 average rating, 376 reviews

On the Beach; Siesta Key SunBum Studio

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

4.86 out of 5 average rating, 105 reviews

Comfy Siesta Key Condo

A spacious bedroom features a large king-size bed dressed in neutral linens. A flat-screen television is mounted on the wall, while natural light enters through sliding glass doors. A small table and a decorative plant add a touch of elegance to the minimalist decor.

4.83 out of 5 average rating, 340 reviews

[Beach Elements] pool view + private beach & bikes

4.86 out of 5 average rating, 142 reviews

A modern living area features a blue sofa with decorative pillows and a low coffee table. A dining set with white chairs is visible in the background. Bright natural light filters through sheer curtains, enhancing the neutral grey walls and stylish artwork.

Condo in Sarasota

Heated Pool Apartment Near Siesta Key | 1BR

4.79 out of 5 average rating, 103 reviews

Beachwalk Townhouse with view of Gulf of Mexico

4.98 out of 5 average rating, 236 reviews

A clear view of the tranquil waters reveals a vibrant blue float anchored in the shallows. The backdrop features a picturesque beachside resort with palm trees, framed by a clear blue sky and soft sandy shorelines.

Condo in Longboat Key

Island Time on LBK!

The exterior of the two-story condo building is visible, featuring a series of balconies adorned with umbrellas. Lush greenery surrounds circular seating areas with white chairs and tables, providing a relaxed outdoor atmosphere. Clear blue skies complement the setting.

4.93 out of 5 average rating, 234 reviews

Private Siesta Key Escape

Other vacation rentals with a pool

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 out of 5 average rating, 91 reviews

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

A clear swimming pool reflects the evening sky, surrounded by a spacious patio. Outdoor seating for dining is arranged under an umbrella, with chairs positioned nearby. Lush greenery provides privacy, and large glass doors lead to the inviting interior of the home.

5 out of 5 average rating, 14 reviews

Pool, Spa, & Private Gym in the Heart of Sarasota

5 out of 5 average rating, 9 reviews

Private Pool +Game Room Near Siesta Key | Sleeps 9

5 out of 5 average rating, 44 reviews

A vibrant outdoor scene showcasing a poolside setting with plush lounge chairs and colorful pool floats. A straw hat and sunglasses rest on a striped towel next to a wicker table adorned with tropical-themed items. Refreshing drinks and fruits are nearby, surrounded by lush greenery.

Villa in Arlington Park

Luxury Pool & Game Retreat • Close to Beaches

Superhost

Home in Bayou Oaks

5 out of 5 average rating, 4 reviews

Sapphire Shores Muse | 2 Bed 3 Bath | Luxe Pool

4.94 out of 5 average rating, 32 reviews

Sarasota Hideaway~ Stay Near Siesta Key

A private heated pool is surrounded by a screened patio, featuring multiple loungers for relaxation. Lush greenery and trees can be seen beyond the pool area, and a fully fenced yard provides privacy. Sunlight reflects off the tranquil water surface.

4.91 out of 5 average rating, 22 reviews

Poolside Oasis | NEWLY Remodeled | Fully Fenced