Holiday rentals with breakfast in Sarasota

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.

Lakefront+Htd Pool+Pickleball+Arcade+Firepit+AMI

“This house is truly a little slice of paradise.” — Galena, 2025 Wake up to lake views, spend your days poolside, and your evenings by the fire pit watching the sun melt into the water. Tree by the Sea is a 5BR lakefront retreat minutes from AMI, designed for friend & families to unplug, play, and reconnect. Pickleball and Bocce matches, putting green practice, corn hole games, shuffleboard, arcade game-room nights, coastal calm, barefoot mornings, and memories that linger long after checkout.

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.

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

Tropical Escape, Sarasota!

Discover Real Florida, UP CLOSE! Unique and tranquil. Enjoy nature & everything Sarasota! • Refreshing breezes: private wrap-around deck • Pets welcome* • Comfortable beds, Towels, Bedding • Fully equipped kitchen • Beach gear, Crib, Bikes • 1st day cont. breakfast • Boat/truck/RV* • Air conditioned, hot water • Special occasions* • EV Charging Station* • Secluded, yet close to Beaches, Parks, Shopping, Dining • Pool & fitness • Sleeps 1-12 • 1400 ft.² * Fees apply

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!

Trophy Fish at the Oasis

Welcome to the "Trophy Fish," a private oasis where resort-style living meets relaxation and fun. Set on a lush half-acre, this retreat offers an in-ground pool and spa, fully equipped outdoor kitchen, putt-putt golf, cornhole, a fire pit, and a 85' TV with extendable arm for movie nights under the stars and views from the pool. Sonos speakers set the perfect soundtrack inside and out. 4 bedrooms, 3 full baths including the outdoor bathroom and shower.

Perfect Location! Steps to Beach~Heated Pool!

Experience coastal luxury at Villa #2 Shrimp 🌴✨, a stylish studio just a 2-minute walk to Manatee Beach 🌊. Enjoy a king bed 👑, spa-like bath 🚿, kitchenette 🍽️, and a private tropical patio 🌿. Relax by the shared resort-style pool 💦, grill out 🍔, or explore nearby shops and dining 🚎🛍️. Dog friendly 🐾 with approval and includes 1 parking space 🚗—your perfect Anna Maria Island escape awaits!

NEW Pickleball | Pool | Playset | 7 min to AMI

Escape to Paradise Palms, a Mediterranean oasis in Palma Sola Park! This 4BR home sleeps 14, perfect for families. Enjoy a private heated saltwater pool, pickleball/basketball court, and game room. Just a 10-min drive to Anna Maria Island's white-sand beaches. Features high-speed WiFi, a fully equipped kitchen, and a cozy screened porch. Your ultimate Bradenton getaway awaits!