Guesthouse holiday rentals in Sarasota
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Sarasota
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Sarasota guesthouses
Family-Friendly guesthouses
Guesthouse in Sarasota
4.97 out of 5 average rating, 236 reviewsCasita Lantana, a 1925 cottage in a Tropical Oasis
Guesthouse in Sarasota
4.99 out of 5 average rating, 102 reviewsSarasota Pool House
Guesthouse in Sarasota
4.98 out of 5 average rating, 130 reviewsThe Mermaid and Corkscrew Loft
Guesthouse in Punta Gorda
4.9 out of 5 average rating, 232 reviewsCharming Cottage
Guesthouse in Bradenton
4.99 out of 5 average rating, 313 reviewsCharming Studio Apartment in Historic Neighborhood
Guesthouse in Sarasota
4.75 out of 5 average rating, 101 reviewsOne Bed Suite near Downtown Sarasota and Beaches
Guesthouse in Gulfport
4.89 out of 5 average rating, 18 reviewsCozy Old Florida Duplex with keyless entry
Guesthouse in Gulfport
4.58 out of 5 average rating, 117 reviewsSpacious Gulfport Studio in Cottage Duplex
Guesthouses with a patio
Guesthouse in Sarasota
4.98 out of 5 average rating, 206 reviewsSiesta Breeze, adorable New Beach Style Studio !
Guesthouse in Bradenton
4.93 out of 5 average rating, 134 reviewsThe Enchantment, Cozy guesthouse,7mi to the beach!
Guesthouse in Sarasota
5.0 out of 5 average rating, 110 reviewsMagical Guesthouse 1 mi from SRQ airport
Guesthouse in Bradenton Beach
5.0 out of 5 average rating, 127 reviewsBradenton Beach Sunsets 1, Anna Maria Island, FL
Guesthouse in Sarasota
4.88 out of 5 average rating, 98 reviewsGuest house w/heated salt water pool and Game Room
Guesthouse in Sarasota
4.96 out of 5 average rating, 27 reviewsDowntown Sarasota Guest House
Guesthouse in Sarasota
4.84 out of 5 average rating, 44 reviewsCocoanut Cottage - Fenced Yard for Pups!
Guesthouse in Sarasota
4.89 out of 5 average rating, 70 reviewsCity Garden Cottage
Guest house rentals with a washing machine and dryer
Guesthouse in Englewood
4.86 out of 5 average rating, 294 reviewsBeach Casita. Private Beach access.
Guesthouse in St. Pete Beach
4.92 out of 5 average rating, 158 reviewsA Hidden Gem Steps to Pass-a-Grille Beach Dogs Ok!
Guesthouse in Sarasota
4.81 out of 5 average rating, 196 reviewsCozy Cottage by the Bay
Guesthouse in Sarasota
4.95 out of 5 average rating, 20 reviewsNEW cottage near Downtown with boat parking
Guesthouse in Sarasota
4.92 out of 5 average rating, 24 reviews*Azure Guesthouse* Walkable! Patio! Beach 8 min!
Guesthouse in Sarasota
4.94 out of 5 average rating, 54 reviewsNew Cozy Wild Cottage near Pinecraft.
Guesthouse in Sarasota
5.0 out of 5 average rating, 36 reviewsRomantic getaway- 1 bdr guest house
Guesthouse in Bradenton
4.98 out of 5 average rating, 41 reviewsSerenity Lake
Quick stats about guesthouse rentals in Sarasota
Total rentals
60 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
4.2K reviews
Destinations to explore
- Anna Maria Island Accommodation & holiday rentals
- Tampa Holiday rentals
- Naples Accommodation & holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- West Palm Beach Holiday rentals
- Boca Raton Accommodation & holiday rentals
- Fort Lauderdale Accommodation & holiday rentals
- Miami Holiday rentals
- Miami Beach Accommodation & holiday rentals
- Key West Holiday rentals
- Havana Accommodation & holiday rentals
- House rentals United States
- Guesthouse rentals United States
- House rentals Florida
- Guesthouse rentals Florida
- House rentals Florida
- Guesthouse rentals Florida
- Cottage rentals Sarasota
- Monthly Rentals Sarasota
- Bungalow rentals Sarasota
- Rentals with a fireplace Sarasota
- Holiday home rentals Sarasota
- Waterfront rentals Sarasota
- Family-friendly rentals Sarasota
- Beach house rentals Sarasota
- Kid-friendly rentals Sarasota
- Rentals with beach access Sarasota
- Private suite rentals Sarasota
- House rentals Sarasota
- Rentals with a hot tub Sarasota
- Condo rentals Sarasota
- Fitness-friendly rentals Sarasota
- Rentals with a kayak Sarasota
- Beach condo rentals Sarasota
- Rentals with pools Sarasota
- Rentals with a fire pit Sarasota
- Rentals with outdoor seating Sarasota
- Rentals with breakfast Sarasota
- Rentals with an EV charger Sarasota
- Townhouse rentals Sarasota
- Boutique hotel rentals Sarasota
- Wheelchair accessible rentals Sarasota
- Rentals with a patio Sarasota
- Smoking-friendly rentals Sarasota
- Pet-friendly rentals Sarasota
- Rentals with a washing machine and dryer Sarasota
- Apartment rentals Sarasota
- Beachfront rentals Sarasota
- Rentals with lake access Sarasota
- Villa rentals Sarasota
- House rentals Kissimmee
- Guesthouse rentals Kissimmee
- House rentals Tampa
- Guesthouse rentals Tampa
- Guesthouse rentals Sarasota County
- House rentals Sarasota County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom