Holiday rentals with breakfast in Sarasota County

Palm Set– Sun Outdoors Resort~Pet Free Home

Palm Set - Resort Home | 2BR, 1.5BA, Sleeps 6 Minimum 7 day booking- Pet Free Home Enjoy Florida resort living at Sun Outdoors Sarasota, one of the area’s most popular resort communities. This clean, well-kept home sleeps up to 6 guests with two private bedrooms and a sofa bed—perfect for families, couples, snowbirds, or longer stays. Designed for comfort and convenience, it’s an ideal home base for relaxing or entertaining , weekly activities for all age , $0 cleaning fee, golf cart included

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

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

Nottingham Beach Bungalow Near Siesta Key Beach!

Book your stay for Spring 2026 now! 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.

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.

Bertram Great Escape Venice, FL

Bring the whole family to this great place with lots of room for fun. Located on Venice Island, this home is your ideal beach getaway vacation property! Our 4-bedroom, 3-bathroom vacation rental offers a unique experience with a private pool, private fenced-in backyard and steps to the Gulf Beach! Our home is available on weekly, biweekly and monthly rental options for that perfect Florida vacation getaway to refresh, recharge and unwind!

Cozy Cottage, FirePit, BBQ, 5 Min Downtown

You’ll love Yesterday’s Sunshine for its vintage Florida charm, calming vibe, and newly renovated comfort. Enjoy two cozy bedrooms, a record player with classic vinyl, a dedicated office space, and a spacious outdoor lounge with BBQ, fire pit, and games. It’s the perfect spot to unwind, slow down, and savor sunny, nostalgic Florida living.

Waterfront Retreat, Heated Pool, Fishing

Step into your dream Florida escape! This 2021 gem offers waterfront living, a heated pool, and a treasure trove of amenities that'll make your heart sing. Dive into family fun by the water, relax in the heated pool, and indulge in a fully stocked haven designed just for you. ◈Experience Port Charlotte With Us & Learn More Below!◈

House With A Boat–Your Private Waterfront Resort

Imagine this: your own private house, your own private dock, and your own private boat — no marinas, no lines, no sharing. If you love boating, fishing, and floating in the pool while the kids chase lizards and cannonball into the water, House With A Boat is your dream escape. Perfect for the Captain and crew — yes, kids included.

Port Charlotte Tropical vacation home

Welcome to this brand new vacation home in Port Charlotte!! Bring your whole family and relax in this beautiful city. 3 Bedroom 2 bath home is conveniently located 15 -35 minutes from finest beaches, Great restaurants, shopping and golf courses are in the area. Take advantage of visiting the Warm Minerals Spring Park.