Boutique hotel vacation rentals in Sarasota County

The spacious bedroom features hardwood flooring and white wooden walls. A king bed with a light patterned coverlet is centered in the room. A small dining table is positioned near a window, and an ensuite bathroom is visible in the background.

4.76 out of 5 average rating, 42 reviews

Bayside Bliss - 1 KING BR, 1 BA; Coffee Shop

Stay in a piece of history! The Bayside Bliss Room on the second floor, is part of the historically significant (former) Charles Ringling estate; now The Reserve Retreat. The property boasts 2 restaurants, coffee/tea shop, wine, craft beer bar. Complimentary drip coffee in our Café (open 8a-2p Fri-Sun). Across the street from Sarasota Bay, & five minutes to Lido Key Beach & St. Armand's Circle. Short distance to Siesta Key Beach downtown & the best Sarasota attractions & cultural destinations.

A bright and airy room features a comfortable king bed with light bedding and decorative pillows. Natural light fills the space through windows adorned with soft blue curtains. A cozy sofa with accent pillows complements the rustic hardwood flooring, while a shelving unit provides additional storage.

4.76 out of 5 average rating, 29 reviews

Mable Ringling Loft 1 KING BR, BA,kitchen downtown

Stay in a piece of history! The 2nd floor Mable Ringling Loft w/ kitchen is part of the historically significant Charles Ringling estate. The property boasts 2 restaurants, coffee/tea shop, wine, & craft beer bar. Complimentary drip coffee in our Café (opens 8a Fri-Sun). Across the street from Sarasota Bay, & five minutes to Lido Key Beach & St. Armand's Circle. Short distance to Siesta Key Beach downtown & the best Sarasota attractions & cultural destinations. We are AirBNB Superhosts.

A bright and airy room features two king-size beds with decorative pillows atop crisp white linens. A mini fridge is placed near the entrance, while large windows allow natural light and offer views of the outdoor surroundings. A cozy seating area is visible in the background.

4.79 out of 5 average rating, 71 reviews

Junior Suite 2 king/beds, private bath

This spacious 2nd floor room was part of the former, significantly significant, Ringling home. The 2-king-bed room is romantically decorated in '20s style. The room faces Tamiami Trail at the 14th St round about, so road noise should be expected. The property boasts 2 restaurants, coffee/tea shop, wine, & craft beer bar. Complimentary drip coffee in our Café (opens 8a Fri-Sun). The other restaurant is upscale with a menu featuring masterfully prepared food from Italy and the Mediterranean.

A spacious bedroom features a comfortable king bed with light linens and decorative pillows. Two bedside lamps provide soft illumination beside matching nightstands. A large window offers natural light and views, while warm wood floors and a decorative rug enhance the inviting atmosphere.

4.72 out of 5 average rating, 81 reviews

August Ringling 1 KING, 1 BA Bay, Beach, Downtown!

This room was originally part of the Ringling family home. The Reserve Retreat has 2 restaurants, a coffee/tea shop & a craft beer and wine bar. The Café is open for breakfast & lunch-Fri-Sun 8a-2p. The room faces Tamiami Tr. at the 14th St round about, so road noise should be expected. Across the street from Sarasota Bay, & five minutes to Lido Key Beach & St. Armand's Circle. Short distance to Siesta Key Beach downtown & the best Sarasota attractions & cultural destinations.

A bright room features a spacious bed with crisp white linens, complemented by a dining area with a small table and chairs. A full-sized refrigerator and a microwave are visible, along with a mirror reflecting natural light from the windows dressed in soft curtains.

4.86 out of 5 average rating, 21 reviews

Reserve Retreat Room 1BR-king/ensuite/kitchn/beach

Stay in a piece of history! Your 2nd floor room is part of the historically significant (former) Charles Ringling estate. The property boasts 2 restaurants, coffee/tea shop, wine, & craft beer bar. Complimentary drip coffee in our Café (opens 8a Tues-Sun). Across the street from Sarasota Bay, & five minutes to Lido Key Beach & St. Armand's Circle. Short distance to Siesta Key Beach downtown & the best Sarasota attractions & cultural destinations. We are AirBNB Superhosts.

A view from the bedroom captures a well-equipped kitchen with white cabinetry and modern appliances. A spacious king bed is dressed in a light-colored quilt, while a comfortable seating area invites relaxation. Natural light filters into the room, creating a welcoming ambience.

4.65 out of 5 average rating, 62 reviews

Charles Ringling 1 KING BR, 1 BA, kit. Bay/Beaches

Stay in a piece of history! The Charles Ringling Room on 2nd floor, is part of the historically significant (former) Charles Ringling estate. The property boasts 2 restaurants, coffee/tea shop, wine, & craft beer bar. Complimentary drip coffee in our Café (opens 8a Thurs-Sun). Across the street from Sarasota Bay, & five minutes to Lido Key Beach & St. Armand's Circle. Short distance to Siesta Key Beach downtown & the best Sarasota attractions & cultural destinations.

Top guest favorite

A bright and airy room is furnished with a queen bed, draped in a light blue patterned quilt. Two wicker chairs are positioned beside the bed, and natural light filters through window shutters, illuminating art pieces with beach themes on the walls.

4.96 out of 5 average rating, 51 reviews

Island House Apartment Motel - Queen bed

Your motel room is crisp and clean inspired by the tranquil colors of our beach. It is 1 of 4 units that share a common hallway on the second floor above the office (no elevator) that do not face the beach. A walk down the stairs and around the building will find your toes in the sand and a lovely view of the Gulf. Our beachfront motel which was built in 1959 and has been in our family since 1960. Guests return year after year to enjoy our location.

Guest favorite

The room features two beds, one full and one extra long twin, each adorned with light, patterned bedding. Soft turquoise accents complement the decor. A window with plantation shutters allows natural light, and a small chair is positioned nearby for added comfort.

4.86 out of 5 average rating, 28 reviews

Island House - Motel Room - 2nd Flr/Full/twin Bed

Your motel room is one of 4 motel rooms on the second floor sharing an interior hallway in our beachfront building, however, they do not face the beach. A simple walk down the stairs and around the corner finds your toes in the sand and you enjoying the beautiful unspoiled beaches of Casey Key. Our guests return year after year and enjoy the sun, swimming in the gulf, and visiting with one another at sunset on the beach.

A bright entryway leads to a kitchenette, featuring a half fridge, coffee maker, and countertop with a small dish rack. Natural light filters through the nearby window, illuminating the neutral-colored walls and laminate wood floors.

4.49 out of 5 average rating, 49 reviews

Casey Key Modern Bayside Cabana w/Private Beach

Just 15 feet from the Venice Inlet, this cabana has just been remodeled with queen tempurpedic bed, kitchenette and roll-in marble shower. The private Gulf beach of Casey Key is just 200 feet from your door on this Gulf to Bay Resort. Casey Key Resort provides a unique experience on Casey Key -- With Gulf Front beach on one side of the property and Venice Inlet waterfront on the other!

A well-equipped kitchen is presented, featuring modern stainless steel appliances, including a refrigerator and oven. Bright white cabinetry contrasts with dark granite countertops. A spacious island provides additional workspace, complemented by two wooden barstools. Natural light is welcomed through the overhead lights and windows.