
Holiday rentals in Osteen
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Top-rated holiday rentals in Osteen
Guests agree: these stays are highly rated for location, cleanliness and more.

Lakefront,Sanford airport, Boombah, Venue 1902,UCF
The lake front cottage is located on a private estate 1 mile south of Sanford airport, 4 miles to Sanford historic district, and 3 miles from Boombha Sports Complex. This cottage has a Fully equipped kitchen, light bright liv/din area, screened wrap around porch. Perfect spot for your next family vacation or weekend get away. While staying at the cottage you are welcome to enjoy our paddle boards and kayaks. Also catch and release fishing. No pets. Discounts for non-refundable cancellations.
LocationFamilyGetting around
4.97 out of 5 average rating, 268 reviews
Guest house on the lake. Trailer parking available
Welcome to our Lakeside Retreat! Nestled along the tranquil shores of a picturesque lake, our Airbnb offers a serene escape from the hustle and bustle. - Enjoy breathtaking views from the private balcony. - Unwind in the cozy living space. - A prime spot for bird lovers! - Kayak, paddleboard, or fish on the lake. This charming getaway blends modern comfort with natural beauty, promising a rejuvenating experience for every guest. Motorcycle parking is available in the garage. Trailers welcome.
FamilyValueComfort
5.0 out of 5 average rating, 78 reviews
Treehouse at Danville
Private Getaway seen on Netflix' Most Amazing Vacation Rentals! Fulfill your dream of staying in a tree house! For safety reasons, this venue is for adults only. We do not allow children or pets. The Treehouse has a tree trunk elevator, private shower, air-conditioning, and real toilet inside so that you can bring your significant other(no compost toilet here). This 18 foot yurt has accent lighting to create the mood of living in the trees on a starry night. Danville is a glamping experience.
LocationValueSleep quality
4.89 out of 5 average rating, 1163 reviews
LakeFront Paradise Retreat
Dear Prospective Guests, Discover serenity at LakeHouse Paradise Retreat, your ideal escape for rejuvenation and quality time with family and friends. Enjoy the peaceful natural environment while being close to Florida’s vibrant attractions, diverse dining, boutique shopping, nightlife, etc. Whether you're headed to Deltona's attractions, the Daytona 500, exploring Daytona Beach, or visiting Disney parks, adventure awaits. Experience the charm of our meticulously curated retreat. Warmly Vera
FamilyLocationLong stay
4.82 out of 5 average rating, 22 reviews
Stunning home with screened patio & fenced yard
Renovated family home in a quiet residential neighborhood. 45 minutes away from Daytona Beach and New Smyrna Beaches, and an hour away from Disney, Universal Studios, Animal kingdom, Epcot, and all Orlando attractions. Deltona is know for its many lakes and Springs. Family friendly and centrally located between Daytona Beach and Orlando parks. Daytona Speedway is only 36 minutes drive. Visiting with an infant, for your convenience, we provide a Playpen, a bouncing seat, and a tub.
LocationFamilyAccess
4.94 out of 5 average rating, 135 reviews
Top-Rated Lakefront Oasis |Fire Pit & BBQ Pavilion
Relaxing at this peaceful lakefront retreat where you can enjoy morning coffee overlooking the water, spend the day fishing or exploring Central Florida, & end the evening around the lakeside fire pit. Perfect for families, couples, & small groups seeking a relaxing getaway near Orlando, Daytona Beach, & beautiful state parks. 2 miles to Publix & CVS, 42 mins to Universal, 56 to Disney & 30 mins to the Daytona Race track. Laundry access is provided. Garage access is not available
ValueFamilyOutdoor spaces
5.0 out of 5 average rating, 65 reviews
Relaxing Studio Suite – Big Bath + Private Entry
Stay in a prime location between Daytona Beach and Orlando! This private studio offers a queen bed and queen sofa bed, perfect for couples, families, or solo travelers. Relax in a spacious bathroom with a walk-in shower and bathtub for ultimate comfort. Just a short drive to top attractions: • 30 min to Daytona Beach ☀️🏖️ • 40 min to Orlando’s theme parks 🎢✨ • 15 min to Blue Spring State Park 🌿💦 Enjoy a peaceful retreat with easy access to adventure!
FamilyValueLaundry
4.91 out of 5 average rating, 79 reviews
Pool + Hot Tub Oasis | Near Beaches & Springs
Your Florida getaway starts here! Unwind by the private screened pool, soak in the hot tub, or catch a game on the outdoor TV while enjoying your own fully fenced backyard. Inside, this stylish 3BR/2BA home comfortably sleeps 6 with plenty of space to relax and reconnect. Pet-friendly and ideally located between Orlando and Daytona Beach, you’re close to Blue Spring State Park, beaches, dining, and some of Central Florida’s best outdoor adventures.
ValueLocationOutdoor spaces
4.99 out of 5 average rating, 72 reviews
Heated Pool Retreat w/ Putting Green, Sleeps 10
Welcome to our Amazing Heated Pool Home — the perfect retreat for family and friends! Now featuring a backyard putting green and pool games, plus our screened, heated pool, a fire pit, and grill on the patio. Stylishly furnished to comfortably sleep up to 10 guests, and pet-friendly so the whole family can join. Just a 20-minute walk from Angela Lake and Dupont Lake, in a quiet Deltona neighborhood — under an hour from Orlando’s theme parks.
LocationValuePets
4.95 out of 5 average rating, 86 reviews
Krater Key Lake House
Welcome to your lakeside retreat like no other! Our Airbnb offers the perfect blend of relaxation and convenience. Indoors, modern comfort meets tech-savvy convenience. Whether you're seeking a serene escape or an action-packed vacation, our Airbnb offers the best of both worlds. Book your stay today and make memories that will last a lifetime.
ValueLocationBreakfast
4.99 out of 5 average rating, 161 reviews
Relaxing Stay with Private Pool/ Near Orlando
✨ Spacious Home w/ Pool near Orlando ✨ Modern & cozy stay just 30 min from Orlando! Sleeps 10: 2 Queen beds, 2 Twin bunks, Queen sofa bed & King air mattress. Enjoy a private pool w/ lounge chairs, free parking (4 cars), full kitchen, fast Wi-Fi, 2 Smart TVs, washer/dryer. Located in a quiet, safe area — perfect for families & groups!
LocationFamilyCondition
4.89 out of 5 average rating, 36 reviews
Lakefront Park Across Street, 3 Blocks to Downtown
Spacious 5 bedroom home in Sanford with a large yard, just 2 blocks from Lake Monroe and downtown dining, shops, and events. Separate billiard room for your private enjoyment is right behind the house. Perfect for families or groups, this inviting home offers comfort, convenience, privacy, and plenty of space to relax and play.
LocationValueSleep quality
4.96 out of 5 average rating, 50 reviewsPopular amenities for Osteen holiday rentals
Other great holiday rentals in Osteen

Chamorro Retreat Home with Heated Pool
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Riverfront Retreat | Private Pool, Free EV Charger
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Cozy Stay
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Bright house located close to beach and attraction
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4.94 out of 5 average rating, 49 reviews
Central Florida Couples Pool Retreat
FamilyLocationAmenities
5.0 out of 5 average rating, 16 reviews
Quiet Escape * Fire Pit * XL Patio * Rain Shower
ValueLocationAmenities
4.88 out of 5 average rating, 42 reviews
Lakefront Retreat w/Hot Tub, Arcade & Sunset Views
FamilyValueSleep quality
5.0 out of 5 average rating, 21 reviews
Entire Home Near Beaches & Parks / Fast WiFi
FamilyValueAccuracy
4.93 out of 5 average rating, 27 reviewsDestinations to explore
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