Guesthouse holiday rentals in Sarasota
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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, 233 reviewsCasita Lantana, a 1925 cottage in a Tropical Oasis
11 – 18 Nov
Guesthouse in Sarasota
4.97 out of 5 average rating, 407 reviewsQuick and Easy Walk Downtown - Tons of Amenities
17 – 24 Nov
Guesthouse in Punta Gorda
4.9 out of 5 average rating, 230 reviewsCharming Cottage
1 – 8 Aug
Guesthouse in Sarasota
4.98 out of 5 average rating, 130 reviewsThe Mermaid and Corkscrew Loft
25 Feb – 4 Mar
Guesthouse in Saint Petersburg
4.79 out of 5 average rating, 257 reviewsSuzette's Hideaway
13 – 20 June
Guesthouse in Sarasota
4.99 out of 5 average rating, 98 reviewsSarasota Pool House
24 Sept – 1 Oct
Guesthouse in Gulfport
4.57 out of 5 average rating, 115 reviewsSpacious Gulfport Studio in Cottage Duplex
24 – 31 May
Guesthouse in Gulfport
4.89 out of 5 average rating, 18 reviewsCozy Old Florida Duplex with keyless entry
22 – 29 June
Guesthouses with a patio
Guesthouse in Bradenton
4.96 out of 5 average rating, 107 reviewsSweet MERMAID #1
22 – 29 July
Guesthouse in Bradenton
4.99 out of 5 average rating, 134 reviewsConch Cottage adorable one bedroom with pool.
26 Aug – 2 Sept
Guesthouse in Bradenton
4.94 out of 5 average rating, 125 reviewsThe Enchantment, Cozy guesthouse,7mi to the beach!
1 – 8 Aug
Guesthouse in Bradenton Beach
5.0 out of 5 average rating, 120 reviewsBradenton Beach Sunsets 1, Anna Maria Island, FL
9 – 16 Jan
Guesthouse in Sarasota
4.83 out of 5 average rating, 40 reviewsCocoanut Cottage - Fenced Yard for Pups!
11 – 18 July
Guesthouse in Sarasota
4.91 out of 5 average rating, 65 reviewsCity Garden Cottage
15 – 22 July
Guesthouse in Sarasota
4.95 out of 5 average rating, 22 reviewsDowntown Sarasota Guest House
9 – 16 Oct
Guesthouse in Sarasota
4.88 out of 5 average rating, 96 reviewsGuest house w/heated salt water pool and Game Room
3 – 10 Sept
Guest house rentals with a washing machine and dryer
Guesthouse in Sarasota
4.83 out of 5 average rating, 190 reviewsCozy Cottage by the Bay
19 – 26 July
Guesthouse in Englewood
4.97 out of 5 average rating, 201 reviewsShabby chic cottage with pool one mile from beach
16 – 23 Apr
Guesthouse in St. Petersburg
4.96 out of 5 average rating, 156 reviewsCasita Blue
Guesthouse in St. Pete Beach
4.92 out of 5 average rating, 153 reviewsA Hidden Gem Steps to Pass-a-Grille Beach Dogs Ok!
26 Oct – 2 Nov
Guesthouse in Gulfport
4.84 out of 5 average rating, 104 reviewsBamboo Carriage House
4 – 11 May
Guesthouse in Englewood
4.87 out of 5 average rating, 293 reviewsBeach Casita. Private Beach access.
24 – 31 May
Guesthouse in Sarasota
5.0 out of 5 average rating, 28 reviewsBeautifully decorated 1bdrm carriage house
27 May – 3 June
Guesthouse in Sarasota
4.95 out of 5 average rating, 20 reviewsNEW cottage near Downtown with boat parking
30 July – 6 Aug
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
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