Pet-friendly holiday rentals in Downtown Sarasota

4.97 out of 5 average rating, 235 reviews

A compact sleeping area is furnished with a wooden bed frame and a colorful assortment of throw pillows. A modern air conditioning unit is mounted above, while a bedside table holds a lamp. Light streams in through the window adorned with wooden blinds.

Flat in Bayou Oaks

Modern Private Apartment 1 Block from Sarasota Bay

One block from Sarasota Bay - completely remodeled and fully furnished guest apartment with a Miami deco feel. The unit is a little over 300 sf with full kitchen, one bathroom w/ shower, comfy queen bed, several stools/ chairs, flat screen tv, wifi, off-street parking, six USB ports for easy charging and sitting area outdoors on front porch. Five minutes to downtown or SRQ airport, 15 minutes to Lido Beach, and 25 minutes to Siesta Beach with easy access to University Parkway or Fruitville Rd.

Flat in Indian Beach-Sapphire Shores

A spacious living area is featured with a large flat-screen television mounted on the wall. Two comfortable chairs are placed adjacent to a round ottoman, decorated with a variety of plants and a small basket. Natural light filters in through large windows, offering a view of the surrounding landscape.

4.97 out of 5 average rating, 161 reviews

Early Chkin, Elevator-4th fl 2mins-DT, 7mins-Airpt

Beach ready Apt!! Echo/white noise machine Beside Ringling College! 2 minutes from downtown Sarasota 7 mins - Airport Corner Apt Steps to the elevator 2 bicycles & 2 escooters Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb that's on a main road . 60+ amenities from a secure room safe to a luxurious, indulgent bed. Essential amenities such as grocery stores/pharmacies/ & CVS. less than a mile away. Send me a message if you have any questions .

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

Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large, screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

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, 179 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 provided beach chairs, umbrella, and cooler 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 nearby or catch Orioles spring training at Ed Smith stadium 1.5 miles away.

Guest suite in Indian Beach-Sapphire Shores

A bright living space is showcased with wooden paneling and a ceiling fan. A cozy bed is adorned with a yellow blanket, while a colorful area rug adds warmth. A seating area with a couch and a workspace are visible, alongside a flat-screen TV and kitchenette.

4.98 out of 5 average rating, 270 reviews

The Sapphire Suite

Beautifully elegant suite with a relaxing touch. A pleasant mix of Hispanic and Modern decor in a newly renovated living area complete with all necessities such as wifi, an outdoor patio and your own free parking. The suite is located MINUTES away from all of Sarasota's famous hotspots! It is down the street from Jungle Gardens. A 10minute walk to The Ringling Museum. 10minute drive to Downtown, 15 minute drive to both Siesta Key and St. Armand's Circle. It could not be located more ideally!

Guest house in Gillespie Park

An outdoor patio area is shown, featuring a round table with four red metal chairs. Potted plants flank the table, and string lights hang overhead, creating an inviting space. French doors lead into the interior, framed by lush greenery.

4.84 out of 5 average rating, 347 reviews

Sarasota Getaway Guest House

Cute guest room with private access, featuring a comfortable queen‑size bed, spacious bathroom, coffee bar with Keurig, microwave & mini fridge. Enjoy a short walk to downtown shopping, dining, live music, Whole Foods, galleries, and fine shops. Gillespie Park is just across the street with tennis, pickleball, basketball, dog‑walking areas, & walking/running paths. You’re only minutes from Lido Beach, St. Armands Circle, Mote Marine, museums, theaters, and Sarasota’s top coastal attractions.

4.91 out of 5 average rating, 180 reviews

Guest suite in Sarasota

Sweet, pet friendly Siesta Suite

Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.

4.88 out of 5 average rating, 295 reviews

A single-story home is surrounded by greenery and palm trees, showcasing a light green exterior. A narrow pathway leads to the entrance, flanked by decorative planters. The white fence adds charm and defines the front yard, with large windows allowing natural light into the interiors.

Villa in Laurel Park

Duplex - just mins to Siesta Beach - Pet Friendly

This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

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, 225 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

4.81 out of 5 average rating, 328 reviews

A cozy sleeping area is showcased with a full-size bed adorned in white linens, complemented by decorative pillows. A large piece of art hangs above the bed, featuring abstract patterns and soft colors. A lamp illuminates the room, and a small window provides natural light.

Flat in Burns Square

Fun Hip Walkable Area by Opera/Water - Studio Apt.

Perfect for those on-the-go or planning to rest in bed & read; this small studio, has cuteness, w/amenities, full-size bed, coffee maker/small refrigerator/small microwave, closet with hangers and small bureau, tiled bathroom, books, hardwood floors, fan and ductless air/heat. Petite and best for one person but two if they love to snuggle. Historic area with shopping/dining/dancing, theaters, comedy club, markets, opera, free local transportation, Bayfront marina, tiki bar+more!

Guest house in Gillespie Park

An outdoor area is shown with a walkway made of red pavers leading to a yellow building. A dining set with an umbrella is situated on a gravel surface, surrounded by potted plants. Decorative stones and landscaping enhance the inviting outdoor space.

4.92 out of 5 average rating, 156 reviews

Perfect Florida location: Craftsman Carriage House

Beautiful accessory dwelling in downtown Sarasota designed to match and complement our historic 1920s bungalow main house, which can be booked separately on AirBnB. The 1BR/1BA carriage house apartment has all modern amenities, with a dedicated garage parking spot and a lovely outdoor porch. The carriage house features Craftsman-style details and is available for short- or long-term stays. Locally-based property management team on-call to ensure a pleasant stay.

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, 123 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 Downtown Sarasota pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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, 114 reviews

Sarasota Getaway “Have some fun under the sun.”

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.

4.88 out of 5 average rating, 122 reviews

Charming Villa 14 mins away from Siesta Key Beach

Superhost

Home in Arlington Park

4.72 out of 5 average rating, 143 reviews

Private house, 3 bed, 2 bath with back yard. WIFI

A modern living area features a light-colored sofa accompanied by a wooden coffee table. The room is enhanced by a large wall art piece depicting a beach scene. An open layout is evident, with a view of a kitchen area and bar seating in the background.

4.91 out of 5 average rating, 133 reviews

15Min to Siesta, Central, Beach Supplies

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, 230 reviews

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

Superhost

A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

4.81 out of 5 average rating, 170 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

A modern kitchen features dark wood cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and dishwasher, are included. A doorway leads to a bright living area where natural light filters through a window, illuminating a cozy seating arrangement.

4.95 out of 5 average rating, 266 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

The exterior of the duplex presents a welcoming entrance with a covered front porch and seating. Lush greenery and small potted plants enhance the home's facade. The driveway is visible, leading to the well-maintained lawn and fenced backyard area.

4.95 out of 5 average rating, 110 reviews

1 Bed 1 bath 7 mins to the beach

Pet-friendly home rentals with a pool

4.89 out of 5 average rating, 108 reviews

The exterior of a pink three-story condo is visible, surrounded by palm trees and tropical plants. A pool area features several lounge chairs and a circular table, with a covered balcony on the second floor. Light clouds decorate the sky, creating a relaxed atmosphere.

Apartment in Sarasota

5213B Menorca Street - Siesta Key Village Condo

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, 116 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Apartment in Indian Beach-Sapphire Shores

The living space features a modern open floor plan with a comfortable blue sofa and a dining area with a stylish light fixture above. A large window provides natural light, and various decorative elements, including plants and wall art, enhance the ambiance.

4.94 out of 5 average rating, 32 reviews

Condo Downtown Sarasota. Sunsets, GYM, POOL/SPA

Home in Downtown Sarasota

4.94 out of 5 average rating, 52 reviews

Serenity Springs | Private Heated Pool + Waterfall

Home in Indian Beach-Sapphire Shores

A vibrant pool is surrounded by a fenced yard, featuring greenery and decorative plants. Two lounge chairs are positioned near the pool, providing a space for relaxation. Sunlight filters through the leaves above, creating playful shadows on the water's surface.

4.94 out of 5 average rating, 66 reviews

Beautiful Florida Bungalow

Apartment in Indian Beach-Sapphire Shores

The view from the patio overlooks Whitaker Bayou, featuring calm waters lined with lush greenery and docks. Sunlight reflects off the water's surface, creating a serene atmosphere. The image captures a tranquil waterfront scene, enhancing the natural beauty of the surroundings.

5 out of 5 average rating, 10 reviews

Charming Waterfront 1/1.5 Beautiful Sunsets!

5 out of 5 average rating, 122 reviews

A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.

Villa in Arlington Park

Luxury Villa with Pool, Game Room, Near Beach

5 out of 5 average rating, 18 reviews

NEW! Renovated Pool Home Mins 2 Siesta Key Beach

Private, pet-friendly home rentals

Home in Downtown Sarasota

The dining area features a wooden table set with placemats and a decorative tray, complemented by light-colored chairs. A small bouquet of flowers adds a touch of nature. The kitchen is visible in the background, showcasing cabinets and a stainless-steel dishwasher against a neutral wall.

4.92 out of 5 average rating, 48 reviews

Fully Equipped Beach Home Near Beaches/Downtown

5 out of 5 average rating, 20 reviews

A private driveway is framed by wooden fences, leading to a residence. Sunlight filters through the nearby palm trees, creating dappled shadows on the gravel surface. The entrance is marked by a wooden gate, adding a sense of privacy to the space.

Flat in Sarasota

Botanical Bungalow at THE BAY

4.99 out of 5 average rating, 80 reviews

The living room features a comfortable beige sofa and a light-colored armchair, arranged around a wooden coffee table. A neutral area rug with a coral design covers the tiled floor. Natural light enters through a window dressed with light curtains, enhancing the tranquil ambiance.

Flat in Sarasota

Tranquil Destination Near Downtown & the Bay!

4.88 out of 5 average rating, 8 reviews

Salt&CitrusSerenity Modern | Private Gated Home

4.98 out of 5 average rating, 52 reviews

An aerial view reveals the vibrant community surrounding this vacation rental, with colorful buildings and lush palm trees. The coastline stretches in the distance, showcasing the beach's sandy shoreline and turquoise waters, while the local neighborhood features a mix of residential and commercial structures.

Townhouse in Siesta Key

100 Steps to beach access & 5-min Village walk

A modern kitchen is highlighted by a central island with a dark countertop and multiple drawers. Sleek white cabinets complement stainless steel appliances, while a coffee maker and kettle are positioned on the counter. A potted orchid adds a touch of color to the space.

4.99 out of 5 average rating, 79 reviews

Luxury Pet friendly home, 2.7miles to Siesta Key!

The exterior of a charming blue house is captured, framed by two palm trees. A small porch with steps leads to the entryway, while white landscaping stones accentuate the yard. Two white lounge chairs are positioned invitingly in front of the house.