Pet-friendly holiday rentals in Downtown 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, 206 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 living space showcases a comfortable seating arrangement, including two black lounge chairs and a stylish dining area. Natural light floods through large windows, illuminating a decorative shelf filled with coastal decor. A circular rug adds a touch of warmth to the wood flooring.

4.96 out of 5 average rating, 129 reviews

5 Star! Walk/Bike DTN ~ 5 mi to Lido Beach Pets Ok

Bright & Comfy Downtown Home | Walk to Main St, Near Trolley to Lido Beach! Centrally located in a quiet downtown neighborhood along the Legacy Bike Trail & Payne Park, this updated 3BR/2BA home is clean, cozy, and filled with coastal charm. Enjoy a screened-in lanai, a large fenced backyard, WiFi, Smart TV , BBQ, beach gear, washer/dryer and carport. Pets welcome! Prime Location: 1 mi to Main St dining. 2 mi to waterfront dining and boat tours. 5 mi to Lido Beach. Take the nearby free Trolley

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.

4.97 out of 5 average rating, 120 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 private pool is surrounded by a spacious patio with paver stones, offering an inviting area for relaxation. Several lounge chairs and a small table with decorative seating are positioned near the water. Lush greenery borders the yard, enhancing the secluded feel.

4.77 out of 5 average rating, 110 reviews

Pool house by the bay

Come stay in our beautiful, Mid-Century Modern, light drenched home just one block from the bay with a private pool. The private yard is surrounded by lush landscaping & the pool is the perfect place to cool off on hot afternoons. The house is spacious & minimally decorated with finds from our world travels. We've recently replaced the bed and the neighborhood is quiet and easy to explore on foot. Note: this is our home, so please expect a warm lived in feel in the space, not that of a hotel.

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, 330 reviews

Sarasota Getaway Guest House

Fully private & not shared with others Seasonal rates commence Nov 1 2023 - April 30, 2024 Longer Term Lower Rate Rentals commence May 1, 2024 - Nov 24 (Long Term rental rates available - please contact) Enjoy the luxuries of staying in the Gillispie Park area Dog Park, Tennis, Pickleball...... Walking distance to downtown where guests can find wonderful dining, entertainment, Saturday morning Farmers Market and much more Close to beaches and Arts and Entertainment and St. Armands Circle

4.87 out of 5 average rating, 223 reviews

A spacious bedroom features a comfortable queen-sized bed with crisp white linens. A large painting of a sea turtle surrounded by colorful fish adorns the wall. A dresser sits nearby, and a cozy sitting area is visible through the open door, enhancing the inviting feel of the space.

Flat in Burns Square

Beautiful Historic District Walkable Near Marina

My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publix, fabulous restaurants, diverse shopping options, performance theaters, movie theaters, nightlife, public transport, boat/water activity rentals, parks, spas, and a short distance to Siesta Key & Lido beach or Sarasota airport. You’ll love my place. It is good for couples, solo adventurers, and business travelers. I have lots of regulars who come back time and time again.

Cottage in Indian Beach-Sapphire Shores

The cottage features a welcoming exterior with a screened-in lanai, framed by decorative beams and charming window boxes. Lush greenery surrounds the property, and a large tree adds to the tranquil setting. A pathway leads to the front door, enhancing the inviting atmosphere.

4.8 out of 5 average rating, 269 reviews

Cozy Cottage by the Bay

Charming and historic decorator cottage near Downtown Sarasota. Located in the highly desirable, quiet, and safe neighborhood of Indian Beach - Sapphire Shores. Just a short drive to some of the nations top rated beaches like Siesta Key Beach. One of the best features of the home is the enclosed lanai at the front of the house. Perfect for enjoying Florida's coveted indoor/outdoor living. It has a private fenced in backyard, with a fire pit. Off street parking for 2 cars in the driveway.

4.9 out of 5 average rating, 166 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, 292 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

4.8 out of 5 average rating, 311 reviews

A bright kitchen area features pale green walls and modern white cabinetry. A sign spells out "BEACH" in decorative letters, accompanied by textured decorative objects. A stainless-steel refrigerator and microwave are visible, highlighting the suite's inviting and fully equipped kitchen.

Guest suite in Sarasota

Studio 10 Mins to Beach w/ Fenced in Backyard

Experience Sarasota like never before in our studio. Immerse yourself in the seaside charm while enjoying the comfort of a home away from home. Perfectly situated in the heart of Sarasota, you'll have easy access to all the must-see attractions, from the pristine Siesta Key beach to the bustling downtown area. Plus, with Sarasota Bay, Marina Jacks, top-rated restaurants, and grocery stores just a stone's throw away, everything you need is within reach. Come live the Florida dream!

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, 134 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

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, 113 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

4.96 out of 5 average rating, 77 reviews

Chic Oasis | Private Heated Pool| Legacy Trail

4.97 out of 5 average rating, 39 reviews

A privately enclosed pool area features a sparkling pool surrounded by lush tropical landscaping. Several loungers provide comfortable seating, with paver stones creating a clean, defined space. Sunlight filters through the screened enclosure, enhancing the serene atmosphere of the space.

Home in Laurel Park

Downtown Sarasota Oasis w/ Heated Pool!

A bright living area features a spacious white sofa centered beneath a large woven light fixture. Tropical plants are situated near large windows that allow natural light to fill the space. A neutral rug complements the light-colored furniture and decor.

4.92 out of 5 average rating, 26 reviews

Coastal Retreat near Siesta Key Beach and Downtown

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.

4.96 out of 5 average rating, 24 reviews

Costal Breeze Cottage. Pet friendly. King size bed

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, 226 reviews

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

4.88 out of 5 average rating, 65 reviews

3BR Beachwood Bungalow Near Beaches & Downtown

A private outdoor space is presented, featuring a heated saltwater pool illuminated by soft lighting. A hammock is hung nearby under a stylish frame, surrounded by lush greenery and a fenced area, enhancing the serene ambiance for relaxation.

4.96 out of 5 average rating, 109 reviews

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

4.97 out of 5 average rating, 143 reviews

Barefoot bungalow. Near beaches and amenities.

Pet-friendly home 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, 73 reviews

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

4.91 out of 5 average rating, 45 reviews

An open kitchen and living area feature modern cabinetry and stainless steel appliances. A large kitchen island provides seating, while a cozy living space is equipped with a sectional sofa and an armchair. Natural light flows through the sliding glass doors, showcasing the outdoor scenery.

Holiday home in Sarasota

Waterside Retreat: Modern 2BR, Mins to Beach & Apt

4.95 out of 5 average rating, 19 reviews

Coastal Luxe, SaltPool/Spa, 5miles to Siesta

4.89 out of 5 average rating, 228 reviews

A welcoming living space is visible through an opening, featuring a comfortable blue chair and a wall-mounted TV. Natural light filters through a window, illuminating the white walls and partially covering a cozy bed with blue and white bedding in the adjacent area.

Guest house in Sarasota

Supercute Beach Themed Retreat Free Parking Wi-FI

5 out of 5 average rating, 11 reviews

Apartment in Sarasota

Poolhouse 1/1, 4 min from Siesta

A private heated pool is enclosed within a screened lanai, surrounded by lush greenery. The pool area features a textured stone surface and a safety railing. Sunlight filters through the overhead structure, creating a bright and inviting atmosphere.

4.86 out of 5 average rating, 133 reviews

Casa Verde Sarasota Retreat

4.86 out of 5 average rating, 128 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.

Apartment in Sarasota

Anchor house +6 min. from Siesta Beach+heated pool

5 out of 5 average rating, 116 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

Tropical Luxury Villa: Pool, Game Room, Near 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.

4.88 out of 5 average rating, 34 reviews

Fully Equipped Beach Home Near Beaches/Downtown

5 out of 5 average rating, 16 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, 73 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!

5 out of 5 average rating, 4 reviews

Comfortable Orange Suite.

5 out of 5 average rating, 18 reviews

Luxury Sport Vacation Pool House-Downtown Sarasota

Home in Rosemary District

An aerial view captures a developed shoreline alongside a serene body of water at sunset. Modern buildings line the waterfront, while lush green spaces and a walkway connect to the natural surroundings. Vibrant colors fill the sky, reflecting on the calm surface of the water.

4.67 out of 5 average rating, 15 reviews

Downtown Sarasota. Bring your pets!

A spacious living area is highlighted by custom vaulted wood ceilings with exposed cedar beams. A large flat-screen TV displays a serene ocean scene. The modern kitchen and dining area are visible in the background, with a comfortable sectional sofa and a round coffee table at the forefront.

4.91 out of 5 average rating, 44 reviews

Designer home minutes from Downtown with Hot Tub

A living area features a yellow sofa accompanied by two blue armchairs, creating a comfortable seating arrangement. A glass coffee table is centered on a textured area rug. Natural light filters through sheer curtains, and a piece of wall art adds a touch of color to the neutral walls.