Guest house holiday rentals in Sarasota
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Top-rated guest house rentals in Sarasota
Guests agree: these guest house rentals 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 guest house rentals in Sarasota
Family-friendly guest house rentals
Guest house in Punta Gorda
4.9 out of 5 average rating, 230 reviewsCharming Cottage
12–19 Mar
Guest house in Gulfport
4.57 out of 5 average rating, 115 reviewsSpacious Gulfport Studio in Cottage Duplex
24 Jun – 1 Jul
Guest house in Gulfport
4.89 out of 5 average rating, 18 reviewsCozy Old Florida Duplex with keyless entry
20–27 Apr
Guest house in Sarasota
4.99 out of 5 average rating, 98 reviewsSarasota Pool House
2–9 Jan
Guest house in Port Charlotte
4.84 out of 5 average rating, 44 reviewsExclusive Apartment in Park Setting
10–17 May
Guest house in Siesta Key
4.95 out of 5 average rating, 21 reviewsSiesta Key Luxurious Beach Cottage
4–11 Oct
Guest house in Sarasota
4.78 out of 5 average rating, 18 reviewsGuest House Get Away! Great Area. Private. Relax!
8–15 Jan
Guest house in Sarasota
4.47 out of 5 average rating, 125 reviewsLa Casa Pequeña - Pool House
14–21 May
Guest house rentals with a patio
Guest house in Bradenton
4.99 out of 5 average rating, 134 reviewsConch Cottage adorable one bedroom with pool.
31 Jul – 7 Aug
Guest house in Bradenton
4.96 out of 5 average rating, 107 reviewsSweet MERMAID #1
24 Sep – 1 Oct
Guest house in Bradenton
4.94 out of 5 average rating, 126 reviewsThe Enchantment, Cozy guesthouse,7mi to the beach!
26 Mar – 2 Apr
Guest house in Bradenton Beach
5.0 out of 5 average rating, 121 reviewsBradenton Beach Sunsets 1, Anna Maria Island, FL
12–19 Jan
Guest house in Sarasota
4.83 out of 5 average rating, 40 reviewsCocoanut Cottage - Fenced Yard for Pups!
22–29 Jun
Guest house in Sarasota
4.91 out of 5 average rating, 65 reviewsCity Garden Cottage
18–25 Jul
Guest house in Sarasota
4.88 out of 5 average rating, 96 reviewsGuest house w/heated salt water pool and Game Room
7–14 Jan
Guest house in Sarasota
4.92 out of 5 average rating, 97 reviewsCozy Heaven Studio I
14–21 Sep
Guest house rentals with a washing machine and dryer
Guest house in Sarasota
4.91 out of 5 average rating, 114 reviewsPerfect Florida location: Craftsman Carriage House
22–29 Sep
Guest house in Sarasota
4.83 out of 5 average rating, 190 reviewsCozy Cottage by the Bay
11–18 Sep
Guest house in Englewood
4.97 out of 5 average rating, 202 reviewsShabby chic cottage with pool one mile from beach
16–23 Apr
Guest house in St. Pete Beach
4.92 out of 5 average rating, 153 reviewsA Hidden Gem Steps to Pass-a-Grille Beach Dogs Ok!
28 Oct – 4 Nov
Guest house in Gulfport
4.84 out of 5 average rating, 104 reviewsBamboo Carriage House
4–11 May
Guest house in Englewood
4.87 out of 5 average rating, 293 reviewsBeach Casita. Private Beach access.
24–31 May
Guest house in Sarasota
5.0 out of 5 average rating, 28 reviewsBeautifully decorated 1bdrm carriage house
27 May – 3 Jun
Guest house in Sarasota
4.95 out of 5 average rating, 20 reviewsNEW cottage near Downtown with boat parking
30 Jul – 6 Aug
Quick stats about guest house 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
4.2T reviews
Destinations to explore
- Anna Maria Island Holiday rentals
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