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Vacation rentals in Holiday, Florida, United States

Gulf Breeze Hideaway 5BR Home Close to Sand & Fun

Gulf Breeze Hideaway 5BR Home Close to Sand & Fun

Gulf Breeze Hideaway 5BR Home Close to Sand & Fun

Gulf Breeze Hideaway 5BR Home Close to Sand & Fun

Gulf Breeze Hideaway 5BR Home Close to Sand & Fun

Gulf Breeze Hideaway 5BR Home Close to Sand & Fun

5 bedrooms·2 baths

Seminole • Florida

1.367,52 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

Fully Equipped Modern 1BR, Grill, Outdoor Lounge

1 bedroom·1 bath

Seminole • Florida

567,84 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

Private Beach Access, Gorgeous Partial Views image 1

Private Beach Access, Gorgeous Partial Views image 2

Private Beach Access, Gorgeous Partial Views image 3

Private Beach Access, Gorgeous Partial Views image 4

Private Beach Access, Gorgeous Partial Views image 5

Private Beach Access, Gorgeous Partial Views

2 bedrooms·2 baths

Indian Shores • Florida

4.89(19 reviews)

1.329,30 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

Direct access to the Weeki Wachee River from the backyard.

Main River Mermaid-Parks 6 cars or 4 cars and a truck with a boat trailer

View from above with kayaks , fire pit and your boat. If you don't have a boat you can rent one.

Float in the 72 degree water right in the backyard.

Mermaid Life!

3 bedrooms·1½ baths

Hernando County • Florida

5(16 reviews)

2.277,00 $ USD gesamt für 3 Nächte

26.–29. Okt. 2026

HOLIDAY VILLAS III- 605

HOLIDAY VILLAS III- 605

HOLIDAY VILLAS III- 605

HOLIDAY VILLAS III- 605

HOLIDAY VILLAS III- 605

HOLIDAY VILLAS III- 605

2 bedrooms·2 baths

Indian Shores • Florida

5(26 reviews)

4.948,63 $ USD gesamt für 7 Nächte

24.–31. Okt. 2026

Holiday Villas III #109

Holiday Villas III, Indian Shores

Holiday Villas III Unit 109

Holiday Villas III Unit 109

Holiday Villas III - #109

1 bedroom·1 bath

Indian Shores • Florida

Beach Cottages #1512

Beach Cottages #1512

Beach Cottages #1512

Beach Cottages #1512

Beach Cottages #1512

Beach Cottages #1512

2 bedrooms·2 baths

Indian Shores • Florida

Davis Islands 3BR | Walk to Dining

Davis Islands 3BR | Walk to Dining

Davis Islands 3BR | Walk to Dining

Davis Islands 3BR | Walk to Dining

Davis Islands 3BR | Walk to Dining

Davis Islands 3BR | Walk to Dining

3 bedrooms·2½ baths

Tampa • Florida

1.399,30 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

Deepest and widest canal with filtration system and fountain to keep the water clear. Floating mat, single and tandem kayaks, SUP, launch and floating dock, fire pit, adirondacks, swing, hammock, picnic table, bbq. Play and swim all day!

Original art work by local artist created just for this tropical space.

Custom built projector movie theater where you can sign into your streaming services and play games, movies and music. Three bean bags, sofa bed and recliner with a kitchenette.

Little Spring Retreat king bed Home Cinema Kayaks

Fully equipped kitchen.

Little Spring Retreat king bed Home Cinema Kayaks

3 bedrooms·2 baths

Spring Hill • Florida

5(79 reviews)

1.063,58 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

Channel-Side/Down Town Tampa /Ybor home

Channel-Side/Down Town Tampa /Ybor home

Channel-Side/Down Town Tampa /Ybor home

Channel-Side/Down Town Tampa /Ybor home

Channel-Side/Down Town Tampa /Ybor home

Channel-Side/Down Town Tampa /Ybor home

3 bedrooms·2 baths

Tampa • Florida

4.98(41 reviews)

737,07 $ USD gesamt für 3 Nächte

25.–28. Okt. 2026

Front of the house with 2 parking in driveway

Tropical Oasis On the Gulf Coast

Tropical Oasis On the Gulf Coast

Tropical Oasis On the Gulf Coast

Tropical Oasis On the Gulf Coast

Tropical Oasis On the Gulf Coast

2 bedrooms·2 baths

Seminole • Florida

610,00 $ USD gesamt für 3 Nächte

8.–11. Nov. 2026

Beautiful details that set this home apart. Oceanfront Luxury home.

Ocean Front with 180 degree views inside the home of the ocean

The most epic sunsets you have ever seen!

Master #1 - King Bed ( There are two of these rooms mirrored on each side of the house)

OceanfrontVilla/Pool/HotTub/8bedroom

8 bedrooms·6 baths

Redington Shores • Florida

5(4 reviews)

7.487,65 $ USD gesamt für 3 Nächte

10.–13. Nov. 2026

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

6 bedrooms·4 baths

Tampa • Florida

3.566,08 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

6 bedrooms·3½ baths

Tampa • Florida

5(55 reviews)

5.989,00 $ USD 5.546,04 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

7 bedrooms·4 baths

Tampa • Florida

3.493,28 $ USD gesamt für 3 Nächte

24.–27. Okt. 2026

Springhill Retreat! 3 Bed, 2 bath!

3 bedrooms·2 baths

Spring Hill • Florida

Night time Pool

Spring Hill, 4 Bedroom, Pool | Golf Course!

4 bedrooms·3 baths

Spring Hill • Florida

Spring Hill gulf cutie with pool!

Spring Hill gulf cutie with pool!

Spring Hill gulf cutie with pool!

Spring Hill gulf cutie with pool!

Spring Hill gulf cutie with pool!

Spring Hill gulf cutie with pool!

3 bedrooms·2 baths

Spring Hill • Florida

4.78(18 reviews)

777,08 $ USD gesamt für 3 Nächte

26.–29. Okt. 2026