Holiday rentals with breakfast in Sarasota

Family Hot Tub Villa w/ Fire-pit + Outdoor Lounge

Welcome to our bright and family-ready Sarasota home, just 15 minutes from Lido Beach and 2 miles from downtown. With 5 bedrooms, a nursery, 2 TV lounges, and hot tub, there’s room for everyone to relax, play, and reconnect. We are a local Sarasota family who loves hosting guests from around the world. Happy to give you our insider tips on best places to eat and drink, secret beach parking, and where to take the kids to the coolest playground. Public teacher discounts available. Message us!

Little Summer House 2/2, heated pool, golf/beach

Once you enter Little Summer House you will have left your worries behind. This turquoise paradise is the cumulus of tranquility, comfort and security with a stylish décor. Indulge yourself watching colorful sunsets from the amazing pool or sink into the memory foam king-size bed. You may spot a butterfly or two around our butterfly garden or whip up a quick snack in the fully stocked kitchen with a coffee station complementary with your stay. Pristine beaches and golf courses are a short drive.

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

Nottingham Beach Bungalow Near Siesta Key Beach!

Book your stay for Winter / Spring 2026 now! Booking November 26th through 2026! 28+ day stays get 30% discount! This cozy Nottingham Beach Bungalow is in a central location with a large fenced-in yard, new sunroom with vinyl windows & AC/outdoor-style living-room , and a backyard firepit for a relaxing evening, we are here to help you have an amazing experience on & off the beach! Situated in a quiet residential cul-de-sac, you are only a short drive to downtown, 10 min to Siesta Key beach.

A Piece Of Sunshine to Enjoy!

Beautiful two bedroom, two bathroom home on a dead end road completely fenced and gated it has a pull out couch, full kitchen, dining room, laundry room, and plenty of space to spread out. Located just 10 miles from Bradenton beach and minutes to Anna Marie island from there. 15 miles to Siesta Key Beach. Sarasota airport is 5 miles away, and Tampa Airport is 47 miles away. There are plenty of places to dine out and plenty of places to visit locally. Ideal space for enjoying time with family.

Unit #1 Free kayak/bikes/walk to beach/fullcottage

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

Beautiful Home in Gulf Gate 4 Miles to Siesta Key!

Beautiful, totally remodeled Gulf Gate Home 4 Miles To Siesta Key Beach. This home has beautiful natural light in every room and has been fully updated with a modern touch. Includes so many wonderful sitting areas: modern living room, screened lanai with dining table, Florida sunroom with amazing farm table and lounge sofa, outside patio with grill and chaise lounges. Walking distance to Gulf Gate Library, Gulf Gate Restaurants and Nightlife. No RVs, Boat, or Jet Skis are permitted.

Lakefront Retreat:Heated Pool+Pickleball+Games+AMI

Welcome to Tree by the Sea, a private lakefront 5BR resort just minutes from AMI. Enjoy a heated pool, pickleball/basketball court, bocce/putting green, shuffleboard, and a sunset firepit lounge by the lake. Inside, relax in two game rooms, play on the Infinity Game Table, and unwind in coastal-themed bedrooms and the hammock grove. Perfect for families and groups. Designed for relaxation, connection, and play, Tree by the Sea delivers a true resort-style experience.

Island Home & Casita, Pool, Golf Cart, Beach

Complimentary golf cart INCLUDED. With a short stroll to warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

Peacock Way by Duncan Real Estate

Welcome to Peacock Way! This lovely 1 bedroom duplex side is tucked away on quiet Peacock Lane for a fantastic island getaway with a private pool. The ground level cottage style rental offers a spacious living area with fully equipped kitchen and bistro breakfast area. The property sleeps a total of 4 featuring the king bedroom and the living room sofa that can convert into a full size sleeper. Enjoy all new furnishings after the recent complete remodel!

Florida West Coast Get-Away

Enjoy Florida's beautiful West Coast in your own cozy, private apartment . One bedroom, living room, kitchenette with breakfast bar, attached bath with shower. Central air and heat. Free wi-fi. Private drive and gated entrance. Everything you will need is here just waiting for your arrival. You'll find this a beautiful place near everything you will need to enjoy your Florida vacation. Not available for guests with infants.

Historic Beasley House with Heated Pool

Welcome to the historic Beasley House, a charming 1926 Mediterranean Revival estate. - 4 bedrooms with 1 king bed and 3 queen beds - Heated courtyard pool and multiple terraces - Fully equipped kitchen and cozy living area - Wi-Fi throughout the property - Antique fixtures and original plank wood floors - Free parking, beach chairs, and cooler included - Located near Siesta Key Beach and top attractions