Holiday rentals with breakfast in Siesta Key

Find and book unique Holiday Accommodation with Breakfast on Airbnb

Top-rated Holiday Accommodation with Breakfast in Siesta Key

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Superhost

Guesthouse in Sarasota

4.69 out of 5 average rating, 13 reviews

Coastal Cottage near Siesta Key Beach

Welcome to Robinhood's, Lil John Coastal Cottage! Cozy & modern, it's a perfect get-away! With a large fenced yard, outdoor dining table & umbrella for 4, a screened in porch area, & firepit for relaxing evenings, you will have an amazing Sarasota experience both on and off the beach! Located on a quiet cul-de-sac street. that is walkable to restaurants, shops, grocery stores, and right across the bridge from Siesta Key (5 miles to the beach)! We're pet friendly for furry friends under 50lbs!

Top Guest favourite

Home in Bradenton

4.97 out of 5 average rating, 89 reviews

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

Superhost

Home in Rosemary District

4.71 out of 5 average rating, 28 reviews

Walk Downtown. Large Villa. Fire Pit + Grill

Relax in this tastefully decorated 4.5 bd/ 3.5 bth downtown Sarasota home near beaches, dining, arts, and Lido Key Beach. Family and pet-friendly with fenced yard, free parking, fast Wi-Fi, multiple King beds, Smart TVs, and self check-in. Walkable, cozy, and custom-tailored for your stay. We love to offer local tips like secret beach spots, hidden gem restaurants, and leave treats like fresh cookies or lemonade upon arrival. WE OFFER A DISCOUNT FOR PUBLIC SCHOOL TEACHERS! Message us for info!

Superhost

Home in Sarasota

4.89 out of 5 average rating, 28 reviews

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.

Top Guest favourite

Home in Sarasota

5 out of 5 average rating, 16 reviews

Tranquil Pool Home Minutes to Siesta Key

Welcome to The Summer Breeze Cottage! This adorable pool home offers everything you will need to have an amazing vacation in one of the most sought-after travel destinations! So, if you are ready to take a plunge in the private pool or relax poolside sipping a cool drink as you enjoy time making memories with family and friends, then this is the place for you! And when you're ready to explore you are minutes to Siesta Key Beach as well as the shops and restaurants of Gulf Gate Village.

Guest favourite

Condo in Sarasota

4.96 out of 5 average rating, 28 reviews

Beautiful lakeview 2 bedroom 2 bathroom condo

Welcome to a private oasis with wi-fi connectivity Relax in the air conditioned Lanai with lake views Just 3 miles from the world-famous Siesta Key Beach & sunset This clean 2nd floor condo has ceramic tile floors throughout, open floor plan with large tv, master bedroom with king size bed and enclosed lanai with full view of the lake When the weather permits just open sliding doors on the lanai to enjoy the fresh breeze! Check out various birds, turtles in their private sanctuary

Top Guest favourite

Campervan/RV in Sarasota

4.99 out of 5 average rating, 86 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

Guest favourite

Home in Bradenton

4.91 out of 5 average rating, 56 reviews

4 Night Disc! 9/14-9/18/Heated Pool/Hot Tub/Games

🚲ELECTRIC BIKE TO AMI/RENTALS AVAILABLE ASK US!🚲 🌞 4 min to Robinson Preserve🌞12 min to AMI 🌞 13 min to Manatee/Bradenton Public Beach 🌞 15 min to IMG Academy 🌞 35 min to Bradenton Motorsports Park 🌞 43 min to Siesta Key Beach 🔥 Heated Pool & Hot Tub 🌞 3 King Suites🌞 Smart TVs in all rooms 🌞 Fully Stocked Kitchen with Coffee Bar 🌞 Free high-speed Wi-Fi 🌞 BBQ with Bar Area, Dining for 10 🌞 Pac-Man Arcade🌞 Shuffleboard 🌞 Disc Golf, Corn Hole, Firepit

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 5 reviews

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!

Top Guest favourite

Guest suite in Bradenton

4.97 out of 5 average rating, 148 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 Pass-a-Grille Beach

4.99 out of 5 average rating, 116 reviews

202 Beautiful Pass a Grille Steps from Beach

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

Townhouse in Port Charlotte

4.95 out of 5 average rating, 116 reviews

Exotic Escape home! w/ Heated Pool & Luxurious Spa

Discover a relaxing, tropical lifestyle on Florida's Gulf Coast. Located in the center and boarder of North Port and Port Charlotte you are close to shopping, beaches, restaurants, game fishing, dinner theaters and golf courses. This home is the perfect combination of quiet beauty, lively activity and friends to share it with. So look no further! We have your perfect get away!