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Compare 1146 Vacation Homes in Osteen with updated reviews, rates, and availability.

Pirates Cove Resort Studios
Balcony view

Pirates Cove Resort Studios

3.0 star property
6.4 out of 10, (119)
"The room was great we booked very last minute. Wasn’t sure to expect. There wasn’t a door or curtain on the closet when you walk in. But otherwise it was really cute and clean. We stopped at the grocery store before we arrived they had accommodations in the room to make food that was nice. There was no interaction with any staff if you need anything. Just a text confirmation. There is a sign book but didn’t even see it till we left. Still super cute the beach was clean. Bummer the pool was...
The price is AED 244
AED 527 total
includes taxes & fees
1 Dec - 2 Dec
Pirates Cove Resort Studios
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!
Front Elevation

Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

9.2 out of 10, Wonderful, (177)
"This little place worked out great for us, close to the marina and plenty of room. Will make this our go-to place when we aren’t staying on our boat. "
The price is AED 272
AED 460 total
includes taxes & fees
1 Dec - 2 Dec
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
Front of home/porch

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

9.6 out of 10, Exceptional, (81)
"Nice and comfy, the host let us extend an extra day on short notice due to the hurricane."
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
Pool, 7 Bed 7 Bath, Direct Oceanfront, 4 Kitchens

Pool, 7 Bed 7 Bath, Direct Oceanfront, 4 Kitchens

9.6 out of 10, Exceptional, (26)
"This property was perfect for our family. It was so spacious, and each bedroom had its own bathroom. The private pool and its proximity to the beach were ideal. Best vacation ever!"
Pool, 7 Bed 7 Bath, Direct Oceanfront, 4 Kitchens
Fire Pit + Grill + 2MI to DT + Long Term Stays!

Fire Pit + Grill + 2MI to DT + Long Term Stays!

10.0 out of 10, Exceptional, (4)
"Julie is a wonderful host. Extremely responsive and very helpful. The property is lovely, well designed + thoughtfully furnished. Breezy easy checkin & checkout. 5 stars all around."
Fire Pit + Grill + 2MI to DT + Long Term Stays!
Lake Front Suite -Close to all Attractions

Lake Front Suite -Close to all Attractions

9.4 out of 10, Exceptional, (62)
"Enjoyed our time here. "
Lake Front Suite -Close to all Attractions
Space Coast / KSC / Beaches / Titusville
Living area

Space Coast / KSC / Beaches / Titusville

9.8 out of 10, Exceptional, (102)
"Everything matched the description, and the host was responsive and nice! Great place for a stay in Titusville."
Space Coast / KSC / Beaches / Titusville
Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park Charmer - Heated Pool Home - Close to everything

9.6 out of 10, Exceptional, (4)
"We stayed for over a week and everything was great! Neighborhood is good, the house was well stocked and communication with the owner with seamless! "
Winter Park Charmer - Heated Pool Home - Close to everything
4 br - 3ba- Sleeps 9 Beautiful Oceanfront Family home with private beach access
House is directly on the beach with private walkway.

4 br - 3ba- Sleeps 9 Beautiful Oceanfront Family home with private beach access

10.0 out of 10, Exceptional, (134)
"We had the pleasure of staying at the Front Row for our wedding weekend and could not have been happier! We had gorgeous weather and the house did not disappoint. There was plenty of room for our whole family to enjoy. The kids (ages 6,10 and 15) played in the beach every chance they got. We had beautiful sunrises and sunsets. This home provides everything you need and was super clean. It was perfect! "
4 br - 3ba- Sleeps 9 Beautiful Oceanfront Family home with private beach access
<br> Salty Pelican Beach House! 300 feet to the Atlantic Ocean!
short walk to beach access

<br> Salty Pelican Beach House! 300 feet to the Atlantic Ocean!

9.8 out of 10, Exceptional, (114)
"Lots of space inside and out! Close to everything in NSB!"
<br> Salty Pelican Beach House! 300 feet to the Atlantic Ocean!
The Launch Pad - Perfect for viewing launches - minutes from beaches
Beautiful, covered, screened lanai overlooking pool and backyard.

The Launch Pad - Perfect for viewing launches - minutes from beaches

9.6 out of 10, Exceptional, (20)
"We had a lovely stay for three nights while we took our family to a wedding. The house was clean and pleasant. Our hosts were very responsive when we needed alittle extra cleaning around the pool and took care of it right away. I recommend this home!"
The Launch Pad - Perfect for viewing launches - minutes from beaches
Deltona Home w/ Saltwater Pool & Sunroom!
Deltona Vacation Rental | 3BR | 2BA | 1,500 Sq Ft | 1 Small Step Required

Deltona Home w/ Saltwater Pool & Sunroom!

10.0 out of 10, Exceptional, (9)
"Our stay was fun in this adorable home."
Deltona Home w/ Saltwater Pool & Sunroom!
Oceanfront Home with Gorgeous View! Perfect for Families
Welcome to LaKaSa House on Hill Street

Oceanfront Home with Gorgeous View! Perfect for Families

9.6 out of 10, Exceptional, (63)
"Master bed sheets were clearly not washed from prior stay which was a little disturbing. Overall a great place to stay. "
Oceanfront Home with Gorgeous View! Perfect for Families
2 mastrs, pvt htd salt lap pool, SPA, 2mins walk to beach - Happy Island Retreat
Pool

2 mastrs, pvt htd salt lap pool, SPA, 2mins walk to beach - Happy Island Retreat

10.0 out of 10, Exceptional, (45)
"Very clean, lots of beach chairs and accessories. Great pool/hot tub too! "
2 mastrs, pvt htd salt lap pool, SPA, 2mins walk to beach - Happy Island Retreat
The Blue Anchor Steps to Beach
Living Room

The Blue Anchor Steps to Beach

9.8 out of 10, Exceptional, (19)
"My family came from SC to Port Orange for my daughter’s wedding. The Blue Anchor Steps to the Beach proved to be an excellent choice for us. It was well stocked and beautifully decorated. The beds were so comfortable. The location could not have been better. We were within 5 miles of everywhere we needed to be.. I highly recommend The Blue Anchor …our stay was amazing!"
The price is AED 416
AED 2,028 total
includes taxes & fees
8 Dec - 9 Dec
The Blue Anchor Steps to Beach
THE CHLOE by EVRH
Living area

THE CHLOE by EVRH

9.4 out of 10, Exceptional, (45)
"it’s was such a cute home the decor is soo cute and it’s a very spacious house"
The price is AED 404
AED 1,899 total
includes taxes & fees
28 Nov - 29 Nov
THE CHLOE by EVRH
THE OLIVIA by EVRH
Living area

THE OLIVIA by EVRH

8.8 out of 10, Excellent, (23)
"Unfortunately, we visited Orlando for to visit a sick family member. When booking, I had originally booked a different place which happened to be no where near the advertised location. The Olivia was our saving grace. The host was very attentive from the very start even before securing the home! When we arrived all my crazy questions were answered immediately. I had trouble with the security system app, but the host was very understanding and made accomadations for my outdated phone. The pool...
The price is AED 364
AED 1,715 total
includes taxes & fees
1 Dec - 2 Dec
THE OLIVIA by EVRH
Ocean Front Beach Home Private Pool/Spa Great Location 6-seat Golf Cart for Rent
Sand Dollar Cottage Private Pool Area

Ocean Front Beach Home Private Pool/Spa Great Location 6-seat Golf Cart for Rent

10.0 out of 10, Exceptional, (60)
"The house was nice though slightly limited on bathrooms. The dishwasher was minimal at best with the stairs leading to the second floor a challenge. That being said, the house was nice for being at the beach on the ocean. The focal point of the house was the real nice pool that was more than expected. Also the easy walk to the beach was perfect. The golf cart is a must with its beach pass. Lastly was the wonderful host, Natasja who couldn't have been nicer. We had a couple of small issues that...
Ocean Front Beach Home Private Pool/Spa Great Location 6-seat Golf Cart for Rent
Luxury beachfront escape in New Smyrna Beach
Living area

Luxury beachfront escape in New Smyrna Beach

10.0 out of 10, Exceptional, (11)
"Everything was exactly as the pictures and description showed. Check in and check out were smooth. Ashley was very quick to respond to any questions or concerns and made sure me and my family were well taken care of. I will keep this place in mind for our next trip to NSB-thanks Ashley!"
The price is AED 1,047
AED 2,586 total
includes taxes & fees
2 Dec - 3 Dec
Luxury beachfront escape in New Smyrna Beach
The Ultimate Lakeside Getaway!
Pool

The Ultimate Lakeside Getaway!

9.4 out of 10, Exceptional, (6)
"We booked this home four our very small, private wedding reception and it was just perfect. The house was very clean and looked just like the pictures. The dining table sat 10 people which was a deciding factor for me when booking. We needed enough seats for our guests to enjoy a lunch after our elopement style wedding. My only regret is we were so busy with the wedding we did not get much time to enjoy the hot tub which overlooked the lake. "
The Ultimate Lakeside Getaway!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Osteen

Fantasy Island Resort, Daytona Beach Shores
Front of property

Fantasy Island Resort, Daytona Beach Shores

3.5 star property
8.4 out of 10, Very Good, (71)
"We were able to check in early. Rooms were clean. They had everything that we needed in our room, such as paper towels, utensils, etc. Friendly staff. Reasonable priced. "
The price is AED 345
AED 504 total
includes taxes & fees
2 Dec - 3 Dec
Fantasy Island Resort, Daytona Beach Shores
Tropical Suites at Sunglow Resort
Pool

Tropical Suites at Sunglow Resort

4.5 star property
8.6 out of 10, Excellent, (26)
"The unit was easy to find and no problems parking. The room has a great layout and decorated beautifully. Awesome view. However, the floor a/c unit needs some help. The arm does not stay in the window and the wind made it whistle - loudly! Also, there is a large air return vent in the hallway that is very rusted. It took away from the beautiful decor and it is such a quick, easy fix. But, that view from the 9th floor was just amazing!!"
The price is AED 244
AED 1,075 total
includes taxes & fees
28 Nov - 29 Nov
Tropical Suites at Sunglow Resort
Pirates Cove Resort Studios
Balcony view

Pirates Cove Resort Studios

3.0 star property
6.4 out of 10, (119)
"The room was great we booked very last minute. Wasn’t sure to expect. There wasn’t a door or curtain on the closet when you walk in. But otherwise it was really cute and clean. We stopped at the grocery store before we arrived they had accommodations in the room to make food that was nice. There was no interaction with any staff if you need anything. Just a text confirmation. There is a sign book but didn’t even see it till we left. Still super cute the beach was clean. Bummer the pool was...
The price is AED 244
AED 527 total
includes taxes & fees
1 Dec - 2 Dec
Pirates Cove Resort Studios
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.