Holiday rentals with breakfast in Sarasota Beach

Exotic Escape home! w/ Heated Pool & Luxurious Spa

Discover a relaxing tropical escape on Florida’s beautiful Gulf Coast! Perfectly located on the border of North Port and Port Charlotte, you’ll be just minutes from shopping, restaurants, stunning Gulf beaches, fishing, golf, dinner theaters, parks, and countless local attractions. Whether you’re traveling with family, friends, or simply looking for a relaxing getaway, this is the perfect place to create lasting memories. So look no further, we have your perfect Florida getaway waiting for you!

Value · Location · Pool

Beautiful lakeview 2 bedroom 2 bathroom condo

Welcome to a private oasis with wi-fi connectivity while embracing nature Relax in the air conditioned Lanai with lake views Only 3 miles to the world-famous Siesta Key Beach & sunset This 2nd fl 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 enjoy the fresh breeze! Check out various birds, turtles in their private sanctuary

Location · Family · Accuracy

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

Family · Location · Check-in

Blue Tide Bungalow

Relax & Play in Paradise – Family Retreat with Pool & Hot Tub and firepit in Bradenton, FL Welcome to your Bradenton getaway! Whether you’re here for the beaches, the ballfields, or simply a warm-weather escape, you’ll feel right at home the moment you arrive. This stylishly furnished 4-bedroom, 3-bath home comfortably sleeps 8–10 guests and offers everything you need for a relaxing and memorable stay. From coffee by the pool to sunset cocktails around the fire pit, no detail is overlooked.

Location · Family · Walkability

BeachHouse:Sleeps 13:Ocean View:Spa:Rooftop Deck

☀️ This 4bdrm/4bath house is perfect for large groups or entertaining. Sleeps 14!!! 3 King beds and 2 bunkbeds (3 Twin, 1 Full), Trundle, & Pullout Sofa. Each room has its own private marble tile bathroom. Go upstairs to the Pool table room with built in bar. Then to the 3rd story Rooftop deck for sunbathing and sunsets. Backyard includes a firepit, 12 person swimspa, putting green, outdoor shower, grill, bikes, & beach amenity shed! Mere steps to the beach itself. Spacious & newly renovated!

Location · Family · Comfort

Nottingham Beach Bungalow Near Siesta Key Beach

Book your Summer 2026 getaway - 30% off stays of 28+ nights. Pet-friendly Nottingham Beach Bungalow near the #1 rated - Siesta Key Beach, downtown, Trader Joe’s, restaurants & SRQ. Enjoy a remodeled bath, stocked kitchen, T-Mobile 5G Wi-Fi, smart-lock self check-in, beach gear, assigned parking for 2 cars, private front-yard dining table & umbrella w/ seating for 4, & a charcoal grill. The shared fenced backyard w/ fire pit & propane grill. Best for 2; sleeps up to 4 to 6 with sleeper sofas.

Value · Location · Check-in

Boutique Style:Heated Pool*Game Rm*Hot Tub*2 Kings

A home with heart. Real art on the walls, cozy textiles, thoughtful touches — this isn’t a cookie-cutter rental. It’s a home that blends comfort and style. Family & Dog Friendly — with surprises. We believe in little moments of joy: a welcome basket to make travel easier, a scavenger-hunt that delights all, and fun details throughout. Enjoy the heated pool, 5 person hot tub in the covered lanai, or relax in the media room on the world's most comfortable couch (according to prior guests).

Family · Location · Decor

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.

Family · Location · Nearby

SIP & RELAX SPECTACULAR SUNSETS CLOSE TO SIESTA

Walk the No 1 beach in America, watch dolphins, wake up to sunny blue skies and the breeze from the bay. Watch spectacular sunsets daily whilst sipping your cocktail. Host your destination wedding - additional arrangements & cost. Located on the inter coastal waterway, a peaceful cul da sac & neighborhood close to Siesta Key. Gaze at the water & garden, spot the dolphins & birdlife. Close proximity to fabulous restaurants, boat/kayak rentals, Siesta Key, Downtown, & St Armands Circle.

Family · Location · Kitchen

LJ's Cottage 2

STEPS TO THE SAND - Welcome to your tranquil oasis on Siesta Key at our first floor 2 bedroom, 2 bathroom beach bungalow style cottage unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Relax in our expansive living/dinning room while watching large 60in TV's, perfect after a long day at the beach. The properties amenities boast private balconies, tiki hut, pool, hot tub, grill, and parking.

Family · Location · Laundry

Cozy Cottage, FirePit, BBQ, 5 Min Downtown

Savor the nostalgia at Yesterday’s Sunshine, a 2-bedroom escape blending vintage Florida charm with modern comfort. Spin classic vinyl on the record player or unwind in the spacious outdoor lounge, complete with a BBQ, fire pit, and games. It’s the perfect spot to slow down and embrace sunny, coastal living. For your peace of mind, exterior security cameras monitor the driveway and entry 24/7. We respect your privacy; no recording devices are located inside the home.

Family · Value · Walkability

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!

Family · Location · Condition