House holiday rentals in Sarasota

A light-filled entryway features a wall of glass shelving with decorative items. Double glass doors provide access to the outdoor space, which is partially visible through the glass. A small mat lies on the floor near the entrance.

4.91 out of 5 average rating, 213 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

An inviting fire pit is surrounded by a circular stone seating area, featuring two Adirondack chairs. Decorative cushions add color to the seating. A spacious, fenced backyard is complemented by a serene evening sky with pastel hues.

4.97 out of 5 average rating, 109 reviews

Cottage w/Fire Pit Near Siesta!

Welcome to "Polka Dotted Pelican" located just a stone’s throw from world famous SIESTA KEY! This charming cottage is completely remodeled & nestled in a quiet neighborhood. Enjoy roasting s'mores around the INCREDIBLE backyard fire pit!! The living area opens to a large covered lanai for outdoor dining & relaxation. Comfortable, clean, & fully equipped! Amenities include high speed Wi-Fi, dedicated workspace, free indoor laundry, & bikes/games/beach chairs. Walk or bike to nearby Gulf Gate.

A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.

5 out of 5 average rating, 117 reviews

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

The exterior of the villa is displayed, featuring a welcoming blue-green door and two large windows framed in white. A small potted plant accents the entrance, while a pathway leads to the door, surrounded by well-maintained grass and greenery.

4.87 out of 5 average rating, 119 reviews

Charming Villa 14 mins away from Siesta Key Beach

This villa close to Siesta Key Beach serves as the perfect escape for those looking to enjoy Sarasota. The property comes fully equipped with amenities such as a BBQ, outdoor umbrella, lounge chairs, beach chairs, pickleball rackets, washer/dryer and carport. Featuring 2 bedrooms, this charming home exudes a warm vibe. You can reach Siesta Key Beach, St. Armands Circle, and Downtown Sarasota in under 15 minutes, making it easy to explore all that Sarasota has to offer during your stay.

A welcoming entryway showcases a simple wooden console table with small potted plants. Above, a serene painting depicting a boat complements the neutral wall. The view to the right reveals a sun room filled with natural light, providing a connection to the private backyard.

4.95 out of 5 average rating, 178 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Newly renovated cozy home with all new furnishings and appliances. 2 bedrooms 1 bathroom with an eat in kitchen, sun room, and comfy living room. Stream shows or work virtually with our high speed WIFI. Grab the beach chairs and umbrella to enjoy Lido Key or Siesta Key Beaches both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the backyard. Several golf courses near-by or catch Orioles spring training at Ed Smith stadium within walking distance.

The studio apartment features a spacious bed with light-colored linens, complemented by two decorative pillows. A sleek brown sofa is positioned in front, adorned with a soft throw blanket. Natural light enters through the window, enhancing the clean and modern design.

4.81 out of 5 average rating, 208 reviews

Comfortable + Functional Private Studio Apartment

This comfortable, clean, and private studio apartment is the perfect spot to relax- whether you're here on business or you've spent the whole day on the beach! Recently remodeled with a dining table to take your meals, hot water, a comfortable bed, and well equipped kitchenette, you will be lacking nothing here. This apartment is a guest suite attached to the main living area of the home and is completely private, however there is a resident who lives in the main part of the home.

An open living area is presented, featuring a blue couch and a wooden coffee table. A dining table with four chairs sits nearby, complemented by a kitchen with white cabinetry and modern appliances. A Christmas tree adds a seasonal touch, while windows allow natural light.

4.96 out of 5 average rating, 103 reviews

2 BR House 1.6 miles from Siesta Key Beach

Discover the charm of Sarasota in our newly remodeled 2BR/1BA vacation home. Just 1.6 miles from beautiful Siesta Key Beach! Enjoy your morning coffee on a brick patio surrounded by flowers and sunshine. Our comfy beds, blackout curtains, and quiet neighborhood ensure a sweet deep sleep. FIOS wifi and three smart TVs; a fully-equipped kitchen; and a sparkling new bathroom with two sinks, huge mirror, and marble shower offer all the comforts and convenience of home. We welcome you!

4.92 out of 5 average rating, 272 reviews

A welcoming entryway features a bright door with a small window and a decorative hanging piece. Light-colored walls surround a cozy seating area with a modern sofa. A simple side table holds a lamp, and framed artwork decorates the walls, complemented by indoor plants.

Home in Gillespie Park

*Downtown home 10min. drive to beach; walk DT*

In the heart of Gillespie Park, this bright & spacious home is a 10 min. drive to Lido Beaches and within walking distance to downtown shops, grocery, farmer's market, opera house, restaurants, bars, live music, tennis, parks, antique shops and performing arts. Old Florida bungalow on the outside, inside, it's updated with new appliances and bathrooms. A banyan tree offers private, shady repose on the back deck w/grill and dining area. Message me for room availability.

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, 114 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!

Home in Indian Beach-Sapphire Shores

A rustic wooden sign with the word 'Welcome' painted in white is displayed prominently. Dried floral arrangements are arranged above the sign, adding a natural touch. A small turquoise glass jar sits nearby, contributing to a warm and inviting entryway.

4.89 out of 5 average rating, 710 reviews

Charming Apt. in old Florida home

Cozy, charming suite in a historic 1920's home. Lots of character and charm. Amazing location. One block from the bay with beautiful sunsets. And just a few miles to the beach and downtown. Clean, comfy and a welcoming host. Great for 1 or up to 3 guests. ****Please read the full detailed description for more information before booking. This is very old home, not fully restored, old Florida house. Owner occupied Non- Smoking guests 🙏 Hope to see you soon

4.98 out of 5 average rating, 438 reviews

The living area features a light-colored sofa and two dark armchairs arranged around a wooden coffee table. Natural light enters through large windows with soft drapes, while a wall-mounted television displays a serene image. Decorative elements include a flower arrangement and artwork.

Home in Arlington Park

The Cottage at Central Park II

If you are looking for the perfect family home to cater to your every need, then look no further! With plenty of space to spread out, natural light that pours into every room, an expansive and private fenced in yard, screened-in porch and outfitted kitchen- 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!

A private backyard features a heated saltwater pool surrounded by a spacious patio area. Sun loungers are arranged along the edge of the pool, while trees and shrubbery provide a sense of seclusion. Soft clouds drift in the blue sky above.

4.95 out of 5 average rating, 122 reviews

Coastal Getaway *With Bikes & NEW Saltwater Pool*

Just outside of Downtown near the Legacy Trail, this home is located in a quiet neighborhood only 15 minutes from the Siesta Key Beach. The home stands out with its bright and airy design, brand new saltwater pool in the private backyard, and its breezy living room. The large master bathroom rain shower is perfect to wash off the leftover sand from the beach. You can also spend your evenings grilling out back or playing corn hole in the patio area.

Popular amenities for house rentals in Sarasota

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The modern kitchen features a large island with a marble countertop, topped with an arrangement of fresh fruits and drinks. A light fixture adds a soft glow above the island, while a cozy seating area with a dark sofa and brick wall can be seen in the background.

4.87 out of 5 average rating, 112 reviews

Sarasota Getaway “Have some fun under the sun.”

A serene pool area features a rectangular swimming pool surrounded by a spacious deck. Lounge chairs are positioned for relaxation, while lush greenery and a wooden fence provide privacy. A decorative statue adds an elegant touch to the tranquil environment.

4.98 out of 5 average rating, 103 reviews

The Oasis

4.93 out of 5 average rating, 177 reviews

Home in Bradenton

Casa Noir | POOL • BBQ • FIRE PIT • GAMES • VIBES

A screened-in pool area features a crystal-clear heated pool with lounge chairs positioned nearby. An umbrella provides shade over a seating area, surrounded by lush greenery and fencing that enhances privacy.

4.95 out of 5 average rating, 229 reviews

Cozy 2BD/2BA with Heated Pool Near Siesta Key

4.92 out of 5 average rating, 382 reviews

A bright and airy indoor space features a coastal-themed rug with a starfish design. Light-colored furniture and a wooden table provide a casual dining area, while large windows allow natural light to fill the room and offer views of the backyard.

Home in Pelican Cove

Beach Retreat•Renovated Pool Patio•Near Siesta Key

The spacious living area features a comfortable couch adorned with patterned pillows, a wooden coffee table, and colorful rugs. Natural light floods in through large windows, and an open layout connects to the dining area and kitchen, which is visible in the background.

4.98 out of 5 average rating, 124 reviews

Sunshine House, close to Downtown

A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.

4.95 out of 5 average rating, 222 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

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, 119 reviews

Luxury Heated Pool Family Home Near Siesta Key/DT

Weekly house rentals

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, 82 reviews

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

4.94 out of 5 average rating, 83 reviews

A serene outdoor space features a circular fire pit surrounded by comfortable seating. Lush greenery enhances the setting, while the warm colors of a sunset fill the sky. The guest house is visible in the background, contributing to a cozy atmosphere for relaxation.

Home in Gillespie Park

Downtown Sarasota Guest House

A charming cottage exterior is surrounded by lush landscaping, featuring vibrant flowering plants and manicured greenery. The front porch is accessed by a walkway, with a welcoming entrance illuminated by natural light. The garage door adds functional design to the home.

4.96 out of 5 average rating, 73 reviews

Coastal Cottage | Oasis w/ Fire Pit + Grill!

Home in Indian Beach-Sapphire Shores

A light-filled living area features a sleek black sofa adorned with green cushions, paired with a glass coffee table. A colorful bookshelf is positioned against one wall, while large windows with unobstructed views invite natural light and views of the surrounding greenery.

4.99 out of 5 average rating, 97 reviews

Magical Secluded Retreat

The exterior of a charming turquoise cottage is framed by a fenced yard, featuring a stony pathway and ample outdoor space. Large trees provide a natural backdrop, enhancing the serene environment of this peaceful neighborhood.

4.97 out of 5 average rating, 31 reviews

Costal Breeze Cottage. Pet friendly. King size bed

5 out of 5 average rating, 29 reviews

A private entrance features a white fence and gate with the number 1825 displayed prominently. The pathway is paved with bricks and flanked by lush greenery and colorful flowers, leading to the home's inviting entrance.

Home in Gillespie Park

The Gecko Bungalow - DT Sarasota

5 out of 5 average rating, 12 reviews

NEW! Renovated Pool Home Mins 2 Siesta Key Beach

5 out of 5 average rating, 62 reviews

A serene outdoor space showcases a sparkling pool framed by lush tropical landscaping. Palms and vibrant plants surround the area, with a flamingo statue in the foreground. Soft lighting from string lights enhances the tranquil atmosphere as the sky transitions to dusk.

Home in Bradenton

Flamingo Royale — Beach Luxury Resort

Private house rentals

A single-story home is surrounded by lush landscaping and palm trees, set against a vibrant sunset sky. The entrance features well-kept plants and a paved driveway leading to the garage. The spacious front yard is meticulously maintained, offering ample green space.

4.97 out of 5 average rating, 36 reviews

The Palm House: cozy, safe, central Sarasota

5 out of 5 average rating, 10 reviews

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.

Home in Arlington Park

Paradise on Prospect w/ Htd Saltwater Pool

5 out of 5 average rating, 18 reviews

Kid-Friendly • Near SRQ • Sleeps 6–8

The outdoor space features a private heated pool surrounded by a spacious patio made of pavers. A floating chipping green is positioned near the pool, with sun loungers arranged for relaxation. A shaded dining area is also visible, perfect for outdoor meals.

4.95 out of 5 average rating, 40 reviews

Palm Breeze Luxury•Heated Pool -Great for Families

A bright and airy living area features a sleek white sectional sofa with decorative pillows. A dark coffee table is centered in front, adorned with two gold vases. Framed art pieces are arranged on the wall, adding a touch of elegance to the space.

4.95 out of 5 average rating, 82 reviews

Siesta Key Escape-8 min to the beach,Spa,Bikes,BBQ

A serene outdoor space showcases a heated pool with a gentle gradient of blue, surrounded by elegant stone paving. The house features large windows that allow soft lighting to fill the interior. Lounge chairs and a dining area await under the warm evening sky.

4.81 out of 5 average rating, 47 reviews

Salt Life Villa with heated pool & outdoor dining

5 out of 5 average rating, 40 reviews

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.

Home in Arlington Park

Sarasota Escape | Minutes to Beaches + Downtown