Vacation rentals with a pool in Southgate

4.97 out of 5 average rating, 131 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 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, 107 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.

4.95 out of 5 average rating, 128 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!

4.92 out of 5 average rating, 146 reviews

Cottage in Sarasota

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Casita Verde blends classic vintage charm with modern comforts. This 2-bedroom, 1-bath home features a 55" flat-screen TV with HD cable and fast Wi-Fi. Relax by the private pool or enjoy peaceful evenings on the deck with your favorite drink. Pet-friendly and conveniently located near Downtown Sarasota on Bahia Vista, with an easy drive to Lido Key, world-famous Siesta Key, and I-75 for day trips and longer adventures. 🌴 Cert# VR24-00152

4.94 out of 5 average rating, 112 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. 🌴

4.97 out of 5 average rating, 359 reviews

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

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!

The outdoor area features a heated pool surrounded by lounge chairs, providing ample space for relaxation. A dining set is positioned nearby, accompanied by an umbrella for shade. Lush greenery and palm trees border the property, complementing the serene atmosphere.

4.92 out of 5 average rating, 112 reviews

Rhodes Retreat - Beautiful Pool and Backyard Space

Bright and newly renovated home for a delightful family escape in Sarasota. Central location near beaches, shopping, and downtown, yet nestled in a serene neighborhood. Short walk to charming Amish Village of Pinecraft. Ample parking, garage, and spacious front yard. Option to book separate secondary unit. Siesta Beach 8.7mi, Lido 5.8mi. VR24-00264

Popular amenities for Southgate rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

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

A modern one-story home is framed by lush landscaping and mature trees. The façade features a sleek, dark exterior with large windows and a symmetrical entrance. A paved driveway leads up to the two-car garage, enhancing the welcoming curb appeal.

4.96 out of 5 average rating, 74 reviews

Stunning New 3 bed 3 bath pool home by Siesta Key!

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, 98 reviews

Modern Organic King Beds Salt POOL/SPA SRQ Escape

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

4.94 out of 5 average rating, 53 reviews

Private Heated Pool Retreat for Two Families

5 out of 5 average rating, 14 reviews

3BR/2BA Pool Home | 5mi Siesta/Lido | 2mi Downtown

Condo rentals with a pool

An aerial view captures the expansive white sand beach and turquoise waters, lined with beachgoers. The surrounding buildings and amenities are visible, including pools and recreational areas, creating a vibrant coastal atmosphere. Cloud patterns add depth to the bright blue sky above.

4.94 out of 5 average rating, 128 reviews

Beautiful White Sand Siesta Key Beach

A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.

4.89 out of 5 average rating, 141 reviews

Crystal House on Siesta Key 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, 377 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 cozy living area is depicted, featuring a comfortable sofa and two light blue armchairs. A wooden coffee table is centered in the space, while a small TV is positioned on a decorative cabinet. Soft lighting from floor lamps enhances the inviting atmosphere.

4.84 out of 5 average rating, 163 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

Condo in Gulf Gate Estates

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

4.89 out of 5 average rating, 184 reviews

Lake View 1BR Condo | Heated Pool Near Siesta

4.98 out of 5 average rating, 237 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!

5 out of 5 average rating, 105 reviews

Condo in Sarasota

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

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, 93 reviews

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

An outdoor dining area is presented next to a heated pool, featuring a table set with plates of food and drinks. A gas grill is nearby, and the pool is enclosed by a mesh screen. Lush greenery is visible through the enclosure, enhancing the serene environment.

5 out of 5 average rating, 13 reviews

Paradise on Prospect w/ Htd Saltwater Pool

Home in Downtown Sarasota

4.96 out of 5 average rating, 48 reviews

Beach Escape+Downtown | large yard/Heated pool

5 out of 5 average rating, 15 reviews

Siesta Key Paradise

5 out of 5 average rating, 47 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

5 out of 5 average rating, 4 reviews

Sapphire Shores Muse | 2 Bed 3 Bath | Luxe Pool

A spacious seating area features comfortable chairs surrounding a modern fire table. A clear view of the salt water heated pool is available through large glass doors. Outdoor furniture is positioned beside the pool, with lush greenery visible in the background.

5 out of 5 average rating, 52 reviews

Sunshine House- Sarasota Pool Retreat