Location

Dates

Guests

Vacation rentals in Holiday, Florida, United States

Angel's Waterfront Home Fishing Dock Heated Pool image 1

Angel's Waterfront Home Fishing Dock Heated Pool image 2

Angel's Waterfront Home Fishing Dock Heated Pool image 3

Angel's Waterfront Home Fishing Dock Heated Pool image 4

Angel's Waterfront Home Fishing Dock Heated Pool image 5

Angel's Waterfront Home Fishing Dock Heated Pool

3 bedrooms·2 baths

Holiday • Florida

5(11 reviews)

$270/ nat(exkl. gebyrer & skatter)

Inviting family area with large tv.

Large Family Home, Near Beaches w/ Heated Pool

Spacious kitchen featuring two dishwasher, with open layout to formal dining area, breakfast nook and family area.

Spacious kitchen featuring two dishwasher, with open layout to formal dining area, breakfast nook and family area.

Large Family Home, Near Beaches w/ Heated Pool

5 bedrooms·3 baths

Tarpon Springs • Florida

3.072,41 $ USD total for 5 nætter

23.–28. sep. 2026

Waterfront Home w/ Heated Salt Water Pool & Spa image 1

Waterfront Home w/ Heated Salt Water Pool & Spa image 2

Waterfront Home w/ Heated Salt Water Pool & Spa image 4

Waterfront Home w/ Heated Salt Water Pool & Spa

Waterfront Home w/ Heated Salt Water Pool & Spa

Waterfront Home w/ Heated Salt Water Pool & Spa

3 bedrooms·2 baths

New Port Richey • Florida

5(15 reviews)

$216 – $390/ nat(exkl. gebyrer & skatter)

Welcome to the Mandalay Manor! Let this lavish retreat be the perfect base for your next vacation on the shores of the Gulf of Mexico.

Cool off in the inviting swimming pool and soak up the sun on the comfy sun lounges.

Are there any pianists in the group? You can have a private concerto in the living room.

The inviting fireplace creates an intimate gathering setting.

Serve your delicious meals easily at the 10-person dining table.

Luxe Waterfront Home w/ Pool★Elevator★Gulf Access

5 bedrooms·4 baths

Tarpon Springs • Florida

4.91(11 reviews)

4.139,00 $ USD total for 4 nætter

30. sep.–4. okt. 2026

Main living space features an open floor plan with smart TV, comfortable seating and a fully equipped kitchen.

Spacious master bedroom with king bed and desk for remote work or getting ready for the day.

Shell path leads to the fire pit amid lush, tropical landscaping.

Hot tub with 8 hydrotherapy jets will soothe sore muscles & melt away stress. Ideal for 3-4 people.

The Florida room is a second living space, separate from the main living area.

Charming Coastal Home Near Top Beaches

3 bedrooms·2 baths

Palm Harbor • Florida

5(32 reviews)

1.960,73 $ USD total for 3 nætter

21.–24. feb. 2027

Back of house - heated pool, sun loungers, sofa set, teak patio table & chairs. pool sink. outside hot/cold shower. shade sail. artificial grass (great for kids). Huge game room, design furniture, hurricane impact windows, super-stocked/pro kitchen!

Living & dining room ; roku TV; guest bedrooms & bathroom to the left; master bedroom to the right (behind kitchen); steps to downstairs & front door in center of pic; private office space just to the right of that.

Living and dining room with marble Saarinen table, Eames chairs, Federicia Stingray chair, leather sofa and a Le Corbusier pony chaise lounger.

Upstairs living and dining area ; access through double doors to patio and pool downstairs

Professional Kitchen with gas cooktop, Miele convection oven & warming drawer, GE convection/micro combo, Nespresso & brew coffee station, blender, waffle iron, reverse osmosis water, and all necessities to make your stay a culinary delight!

3800 SQFT waterfront home near beach, heated pool

5 bedrooms·3 baths

Port Richey • Florida

4.9(39 reviews)

3.415,00 $ USD total for 6 nætter

23.–29. sep. 2026

Gulf Access| Heated Pool| Dock| Kayaks&Bikes| Ramp

Gulf Access| Heated Pool| Dock| Kayaks&Bikes| Ramp

Fish from the dock with the provided fishing poles or just take in the wildlife. There are always birds, fish, and sometimes manatees can be spotted from the dock.

Enjoy a hotdog roasted on the fire or s’mores at the end of a fun day in the sun!

Gulf Access| Heated Pool| Dock| Kayaks&Bikes| Ramp

Gulf Access| Heated Pool| Dock| Kayaks&Bikes| Ramp

3 bedrooms·2 baths

Port Richey • Florida

5(3 reviews)

952,00 $ USD total for 3 nætter

23.–26. sep. 2026

Chris and Sarah’s Palm Harbor, FL Beach Getaway!

Chris and Sarah’s Palm Harbor, FL Beach Getaway!

Chris and Sarah’s Palm Harbor, FL Beach Getaway!

Chris and Sarah’s Palm Harbor, FL Beach Getaway!

Chris and Sarah’s Palm Harbor, FL Beach Getaway!

Chris and Sarah’s Palm Harbor, FL Beach Getaway!

3 bedrooms·2 baths

Palm Harbor • Florida

5(17 reviews)

1.857,84 $ USD total for 6 nætter

23.–29. sep. 2026

Waterfront in paradise!

Waterfront in paradise!

Waterfront in paradise!

Waterfront in paradise!

Waterfront in paradise!

Waterfront in paradise!

3 bedrooms·3 baths

Palm Harbor • Florida

2.740,09 $ USD total for 14 nætter

23. sep.–7. okt. 2026

Sit back and enjoy this beautiful coastal home where u can relax and enjoy what Florida can offer.

Pool home minutes from the beach. image 2

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Pool home minutes from the beach. image 4

Pool home minutes from the beach.

3 bedrooms·2 baths

Palm Harbor • Florida

5(33 reviews)

$200/ nat(exkl. gebyrer & skatter)

Coastal Cottage Near Beaches w/ Golf Cart Rental! image 1

Rent our Golf Cart, "Bolt" !

Coastal Cottage Near Beaches w/ Golf Cart Rental! image 3

Coastal Cottage Near Beaches w/ Golf Cart Rental! image 4

Coastal Cottage Near Beaches w/ Golf Cart Rental!

2 bedrooms·2 baths

Palm Harbor • Florida

4.99(71 reviews)

$201 – $748/ nat(exkl. gebyrer & skatter)

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

1 bedroom·1 bath

Dunedin • Florida

5(93 reviews)

510,00 $ USD total for 3 nætter

28. sep.–1. okt. 2026

Hang out at the tiki bar and enjoy the surround sound!

Waterfront home w/dock - access to Gulf of Mexico

Enjoy kayaking with our 11.5ft ocean kayaks!

Waterfront home w/dock - access to Gulf of Mexico

Many kayakers see dolphins in the mangroves!

Waterfront home w/dock - access to Gulf of Mexico

2 bedrooms·1 bath

Port Richey • Florida

5(90 reviews)

3.599,00 $ USD total for 28 nætter

10. okt.–7. nov. 2026

Enjoy swimming in the waterfront heated pool

Open concept living room with large sectional sofa, smart TV, slider to pool deck and open to kitchen and dining area

Guest bedroom with queen and full beds, hotel quality bedding, usb bedside lamps & nighstands, dresser, closet, ceiling fan and smart TV

Main bedroom with hotel quality bedding, USB lamps, en-suite bathroom, smart TV, walking closets, dresser, slider to pool deck, ceiling fan and vanity/workstation

Guest bedroom with queen and full beds, hotel quality bedding, usb bedside lamps & nighstands, dresser, closet, ceiling fan and smart TV

Gulf Access| Docks| Game Rm| Fishing| Heated Pool

3 bedrooms·2 baths

Port Richey • Florida

$200 – $325/ nat(exkl. gebyrer & skatter)

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 1

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 2

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 3

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 4

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 5

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber

2 bedrooms·1 bath

Palm Harbor • Florida

4.86(74 reviews)

$199/ nat(exkl. gebyrer & skatter)

3 bed/2 bath Home W/ Gulf Water Access image 1

3 bed/2 bath Home W/ Gulf Water Access image 2

3 bed/2 bath Home W/ Gulf Water Access image 3

3 bed/2 bath Home W/ Gulf Water Access image 4

3 bed/2 bath Home W/ Gulf Water Access image 5

3 bed/2 bath Home W/ Gulf Water Access

3 bedrooms·2 baths

Palm Harbor • Florida

4.74(50 reviews)

$200 – $250/ nat(exkl. gebyrer & skatter)

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 1

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 2

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 3

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 4

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 5

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona

2 bedrooms·1 bath

Palm Harbor • Florida

4.85(62 reviews)

$200 – $250/ nat(exkl. gebyrer & skatter)

PALM HARBOR| Heated Pool| Games| Office

Step into the spacious dining room that exudes the elegance of a magazine cover.

The adults enjoy a relaxed conversation, occasionally glancing over at the children, full of energy and enthusiasm, are happily engaged in their playful activities in the pool.

A dining table, capable of accommodating up to 10 guests, takes center stage, beckoning family reunions and memorable gatherings with friends.

PALM HARBOR| Heated Pool| Games| Office

PALM HARBOR| Heated Pool| Games| Office

4 bedrooms·2 baths

Palm Harbor • Florida

5(38 reviews)

1.312,00 $ USD total for 3 nætter

23.–26. sep. 2026

The Corner Cottage image 1

The Corner Cottage image 2

The Corner Cottage image 3

The Corner Cottage image 4

The Corner Cottage image 5

The Corner Cottage

2 bedrooms·1 bath

Palm Harbor • Florida

4.94(18 reviews)

$165/ nat(exkl. gebyrer & skatter)

Odessa Lakeside: 3BR Pool & Hot Tub

Odessa Lakeside: 3BR Pool & Hot Tub

Odessa Lakeside: 3BR Pool & Hot Tub

Odessa Lakeside: 3BR Pool & Hot Tub

Odessa Lakeside: 3BR Pool & Hot Tub

Odessa Lakeside: 3BR Pool & Hot Tub

3 bedrooms·3 baths

Odessa • Florida

4.144,00 $ USD total for 3 nætter

25.–28. mar. 2027

Hudson retreat, 3 Bedroom Pool Home!

3 bedrooms·2 baths

Hudson • Florida

Welcome to Emperor Rentals!

Aerial view of the neighborhood and the beautiful spots in the area surrounding the property. Who wouldn't love that? Have questions? Send us a message now!

Share great stories with family and friends while having amazing meals in this lovely dining area! This is the best time to catch up! Inquire now!

Please note that boat docking is not allowed at this property. The dock is currently not accessible and is not available for guest use.

Who wouldn't love this beautiful living area with comfortable L-shaped couch? Have the best time with family and friends here! Book this property now!

Hudson Harbor Hideaway

3 bedrooms·2 baths

Hudson • Florida

5(13 reviews)

671,16 $ USD 604,12 $ USD total for 3 nætter

23.–26. sep. 2026

Luxury Waterfront Villa w/ Pool, Jacuzzi

Luxury Waterfront Villa w/ Pool, Jacuzzi

Luxury Waterfront Villa w/ Pool, Jacuzzi

Luxury Waterfront Villa w/ Pool, Jacuzzi

Luxury Waterfront Villa w/ Pool, Jacuzzi

Luxury Waterfront Villa w/ Pool, Jacuzzi

6 bedrooms·4 baths

Walton County • Florida

4.93(14 reviews)

4.545,00 $ USD total for 3 nætter

23.–26. sep. 2026

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Tampa Event Compound, Hot Tub Bar

Tampa Event Compound, Hot Tub Bar

10 bedrooms·10 baths

Tampa • Florida

5(48 reviews)

21.590,00 $ USD 18.426,50 $ USD total for 7 nætter

23.–30. sep. 2026