Holiday rentals with breakfast in Siesta Key

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Top-rated Holiday Accommodation with Breakfast in Siesta Key

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Guest favourite

Home in Sarasota

4.95 out of 5 average rating, 63 reviews

Beach + Downtown! Saltwater Pool, Spa, Bikes

Unwind and relax at this stunning modern house located in a quiet neighborhood, minutes from Downtown Sarasota. This newly renovated 4 bedroom/3.5 bathroom is the perfect retreat for your family vacation. Enjoy our lush backyard with pool and grill, open-concept living room, chef kitchen, and kid's entertainment. Non-Toxic: 100% Natural and Scent-free cleaning products and UV sanitization are used for turnovers. For guests, we provide organic shampoo/conditioner/soap and filtered water & ice

Superhost

Home in Sarasota

4.89 out of 5 average rating, 27 reviews

Near Siesta Key, Anna Maria, & IMG + Heated Pool

Gorgeous kitchen w/ brand new appliances, heated POOL HOME located in Whitfield Estates! Near Sarasota Airport. - Just 7 mi from downtown Sarasota and Downtown Bradenton - 15 mi to UTC & UTC Mall! - Close by to the historic Sara Bay Country Club, The Ringling Museum School of Art & Design, University of South Florida, IMG Academy, & Asolo Repertory Theatre. - All of that while just a short drive away from beautiful beaches - 8mi to Lido Beach and 13mi to Siesta Key! Your home away from home!

Guest favourite

Bungalow in Sarasota

4.94 out of 5 average rating, 132 reviews

West of Trail Home Near SMH, Siesta & Lido Key

This renovated, mid-century home - rarely available in Cherokee Park/West of Trail area - is safely situated among multi-million dollar homes and gorgeous large oaks. No need for a car with biking distance to Siesta Key, downtown Sarasota, Sarasota Memorial Hospital and Bayfront Park. Walk to Southside Village shops & restaurants, or Selby Gardens. Take a stroll in this walkable neighborhood to see the sun set over the water down the street. This 2/2 home makes for the vacation of a lifetime.

Guest favourite

Guest suite in Bradenton

4.96 out of 5 average rating, 85 reviews

Holiday Heights Hide-a-way

2 bdrm duplex (choice of twin beds or king in 2nd bdrm) with full bed in the other and a baby's pack n play, full kitchen, private entrance, carport and lanai. 7 miles from Anna Maria Island on the Gulf of Mexico, and a few hours from Disney and water parks. A quiet, working-class neighborhood with other children. The owners are retired and are familiar with the area, and happy to make their guests stay a memorable one. It will be like having your own concierge. Let your adventure begin today!

Guest favourite

Home in Ruskin

4.95 out of 5 average rating, 165 reviews

Private Beach Nature 2 ppl pets Work space remote

Unique, modern beachfront guest house-sits on a MULTI million $ property. Blend of Frank Lloyd Wright & Luis Barragan design. Located on Tampa Bay btwn Sarasota and Tampa/St Pete. Surrounded by palm trees, mangroves, birds chirping, dolphins, manatees, waves gently lapping and breezes. Sand from door to private beach. Fresh sheets, outdoor shower, small fridge, microwave, air fryer, & in and outdoor seating areas. Kayak and paddle board available. SUNRISE'S UNIQUE We are DOG FRIENDLY!

Guest favourite

Campervan/RV in Sarasota

4.99 out of 5 average rating, 76 reviews

HOME HOME ON THE RANCH. SARASOTA FL.

My place is great for couples, solo adventurers, and business travelers. Who love the great outdoors and love nature at its best! Lots of wild life to enjoy including our horses, piggy Miss Daisy Mae, Chickens, and they will even share their organic eggs with you every morning 🐣All on our property. You are welcome to take photos to also share your awesome memories. Enjoy our fabulous sunsets!🌞walk our Canopy Roads, Myakka State Park, and The Crawling Museum. Entire home, Camper/RV

Superhost

Home in Anna Maria

4.9 out of 5 average rating, 41 reviews

Gulf Coast Paradise

Located at the North End of Anna Maria Island 3 blocks from the beach and 1 block from the bay. Brand new heated swimming pool. Three bedrooms, 2 baths with open living & dining floor plan. A large screened porch for ping pong and dining. Perfect for entertaining your friends and family. House is equipped with beach chairs, beach towels, boogie boards and toys for your day at the beach. Children supplies available upon request. Pak n Play, crib etc.

Superhost

Condo in Sarasota

4.7 out of 5 average rating, 27 reviews

LJ's Cottages 3

BALCONY VIEWS - 2 bedroom, 2 bathroom second floor bungalow style unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Our massive living room and dining area are perfect for watching large 60in TV's with entertainment packages to relax after a long day at the beach. The properties amenities boast private balconies, tiki hut, pool, hot tub, grill, and parking.

Guest favourite

Guest suite in Bradenton

4.97 out of 5 average rating, 123 reviews

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.

Guest favourite

Apartment in Saint Pete Beach

4.94 out of 5 average rating, 100 reviews

302 2 BR in Pass a Grille - Gulf & Bay Views

The Berkeley Beach Club is inspired by all that is Pass-A-Grille Beach: a funky, fun beach community, unique shopping, gorgeous beaches and breathtaking sunrises and sunsets. It is, in a word, Paradise. This lovely building, inspired by classic beach architecture, is on historic 8th Avenue in the heart of Pass-A-Grille. Walk a short block to the Gulf of Mexico beach to the west or Boca Ciega Bay to the east.

Guest favourite

Home in Sarasota

4.98 out of 5 average rating, 40 reviews

Pool House Paradise

Located in the highly sought after Gulf Gate neighborhood, 2 miles from Siesta Key, this home is sure to turn your moments into memories! This 4 bedroom, 2 bathroom home features on open floor plan, granite countertops, stainless steel appliances and updated bathrooms. The yard is fully fenced, so feel free to bring along your pets!

Guest favourite

Home in Sarasota

4.81 out of 5 average rating, 128 reviews

Vacation Paradise Close to Beach!

Fantastic vacation spot with a luxurious screened in private heated pool - this spacious house has all the amenities of home so you'll never want to leave! Just a quick 7-10 minute drive to the beautiful free public beach, 12 minutes to fun Siesta Village, and 20 minutes to St Armand's Circle with tons of shops and restaurants!