Holiday rentals in Sarasota

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Top-rated holiday rentals in Sarasota

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

Flat in Sarasota

5 out of 5 average rating, 196 reviews

Modern Luxury Apartment in a House Near Siesta

Large modern construction 950 square foot 1 bedroom apartment. Beautifully furnished, efficient apartment attached to the side of the main house. This unit has a private entrance with bright, modern interior and high ceilings. The apartment offers 1 King bed. The full bathroom has a large shower. A Washer and dryer located inside the apartment. Nestled on a quiet street with easy access to Siesta key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key. Great location!

Top guest favourite

Home in Bellevue Terrace

5 out of 5 average rating, 102 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream! From the swings at the dining room table and the neon sign, to the moss wall and the private putt-putt course, Living the Dream is fully loaded and is the ultimate luxury vacation home! Located just 15 minutes away from BOTH Lido Key and Siesta Key Beach, this incredible stay includes: ✔ Backyard Putt-Putt Course ✔ Private Heated Saltwater Pool w/ Lounge Chairs ✔ Covered Patio w/ String Lights ✔ Jura Espresso Machine ✔ 65" Frame TV w/ Youtube TV Included!

Guest favourite

Home in Sarasota

4.91 out of 5 average rating, 190 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

Top guest favourite

Flat in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 171 reviews

ROYS PLACE Romantic, Private, Paradise!

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR THREE YEARS. "I LOVE ROYS PLACE!" Words most commonly used by guests in reviews are "quality" "clean" "cute" "sexy" "cool" "safe" . This is a restored 600 sq. ft. one bedroom apartment in an old historic home located in the heart of coveted safe Northwest Sarasota. Offered for you, a romantic boutique apartment with your own private (exclusive to you, not shared) CLOTHING OPTIONAL lanai, outdoor shower and heated pool.

Top guest favourite

Guest suite in Sarasota

4.99 out of 5 average rating, 183 reviews

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

Guest favourite

Tiny home in Sarasota

4.96 out of 5 average rating, 358 reviews

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

Guest favourite

Home in Sarasota

4.93 out of 5 average rating, 122 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

Guest favourite

Home in Gillespie Park

4.9 out of 5 average rating, 105 reviews

Saltwater Pool & Hot Tub-Gas Grill-Bikes-Baby Gate

The House - Sleeps 12 people. -Saltwater heated pool -4 person hot tub -Kid’s toys & accessories, including stroller, carseat, highchair, pack and play, etc… -Bikes! -Stocked kitchen -King beds. Location: - 5 minute walk to downtown, 8 minute drive to Lido Key Beach. -Directly next to our “sister house” … book both for huge groups! Hosts -Small family run side-business. We love connecting with visitors! WE OFFER A DISCOUNT FOR PUBLIC SCHOOL TEACHERS! Message us for info!

Guest favourite

Guest suite in Sarasota

4.93 out of 5 average rating, 219 reviews

MG Tropical Stay. With private entrance and patio.

Welcome to our one year old Guest Room.(Adults only). The attached Modern open concept studio style room is all yours with your own: kitchennete, bedroom, bathroom, and secluded patio! no shared spaces at all. With private entrance and two cars parking space. Quiet location -Spotless upon arrival We are welcoming you to our place! Location is 3.8 miles from downtown 7.9 miles from Lido Key Beach and less than 5 miles from Main Mall, UTC Shopping, and Restaurants areas.

Guest favourite

Home in Arlington Park

4.96 out of 5 average rating, 124 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.

Guest favourite

Home in Sarasota

4.93 out of 5 average rating, 187 reviews

Sea-esta Cottage- Cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand-new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

Top guest favourite

Home in Indian Beach-Sapphire Shores

4.9 out of 5 average rating, 671 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