Holiday rentals with breakfast in Sarasota Beach

Lil John Coastal Cottage near Siesta Key Beach

Book your Summer 2026 Sarasota getaway-30% off stays of 28+ nights. Welcome to Robinhood's, pet-friendly Lil John Coastal Cottage is a cozy private guesthouse, located on a quiet cul-de-sac street near #1 ranked Siesta Key Beach, downtown, Trader Joe’s, restaurants & SRQ. Enjoy smart-lock self check-in, T-Mobile 5G Wi-Fi, coffee essentials, a comfortable bedroom, sleeper sofa, a screened in porch area, outdoor dining table & umbrella for 4, & shared outdoor spaces, a fire pit, in a fenced yard.

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

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.

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 (rates incl 2 guests*) • 1400 ft.² * Fees apply

Hot Tub Oasis - Sleeps 16 - Near Beach & Downtown

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, 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!

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.

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.

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

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.

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.

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!

The Shady Mermaid by Duncan Real Estate

Welcome to The Shady Mermaid! A luxury ground-level vacation home just a 3-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen has ample counter space, gas cook top and oven, extra-large fridge/freezer and wine cooler making meal prep a breeze.