Welcome to Dock Holiday! Bright waterfront living with beautiful harbor views and Clearwater Beach just a 5-minute walk away.
Relax on your private balcony overlooking the harbor—perfect for morning coffee or an evening glass of wine.
Private KING bedroom with TV, ceiling fan, charging stations and plenty of storage.
Two QUEEN beds make this spacious second suite ideal for families, friends, or groups who want comfortable sleeping arrangements and plenty of room.
Enjoy the heated bayfront swimming pool and sundeck—perfect for swimming, lounging, and relaxing with beautiful harbor views.

Dock Holiday, #205 Walk to Beach! Pool + Free Parking + Beach Gear

2 bedrooms·2 baths
Clearwater • Florida
5(198 reviews)

$ 1.112,69 USD total por 3 noites

29 de nov. – 2 de dez. de 2026

Dockside Duo = TWO complete side-by-side waterfront condos—perfect for families and friends traveling together.
Beautiful harbor views from your private balconies—start the morning with coffee by the water.
Condo #1 – Dock of the Bay: Spacious waterfront living room with sleeper sofa, Roku TV and Cable.
Condo #2 – Dock Holiday: Bright waterfront living room with sleeper sofa, Roku TV and Cable.
Condo #1 – Dock of the Bay: Comfortable KING bedroom with TV, ceiling fan, charging stations and ample storage.

Dockside Duo, #204 & #205 Side-by-Side Waterfront Condos | Walk to Beach

4 bedrooms·4 baths
Clearwater • Florida
5(7 reviews)

$ 2.812,07 USD total por 4 noites

7 – 11 de dez. de 2026

Harborview Grande #405
Harborview Grande #405
Harborview Grande #405
Harborview Grande #405
Harborview Grande #405

Harborview Grande #405

3 bedrooms·2 baths
Clearwater • Florida
5(71 reviews)

$ 2.145,95 USD total por 4 noites

8 – 12 de nov. de 2026

Welcome to your home away from home!
This large pool and spacious patio will make it hard to decide if you want to go to the beach or stay in.
Renovated inside and out!
Double sinks, soaker tub and walk in shower!
This brand new kitchen is stocked with everything you need for your meals in!

Twin Oaks Retreat

5 bedrooms·3 baths
Clearwater • Florida

$ 1.129,69 USD $ 1.046,12 USD total por 3 noites

9 – 12 de nov. de 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)

$ 1.841,94 USD total por 6 noites

8 – 14 de nov. de 2026

Gulf Breeze Getaway - Sand Key image 1
Gulf Breeze Getaway - Sand Key image 2
Gulf Breeze Getaway - Sand Key image 3
Gulf Breeze Getaway - Sand Key image 4
Gulf Breeze Getaway - Sand Key image 5

Gulf Breeze Getaway - Sand Key

2 bedrooms·2 baths
Clearwater • Florida

$ 5.650,00 USD total por 30 noites

8 de nov. – 8 de dez. de 2026

Peaceful Pond Paradise
Peaceful Pond Paradise
Peaceful Pond Paradise
Peaceful Pond Paradise
Front seating area

Peaceful Pond Paradise

3 bedrooms·2 baths
Largo • Florida
5(10 reviews)

$ 582,00 USD total por 3 noites

21 – 24 de nov. de 2026

Funshine Flamingo's Nest
Funshine Flamingo's Nest
Funshine Flamingo's Nest
Funshine Flamingo's Nest
Funshine Flamingo's Nest

Funshine Flamingo's Nest

1 bedroom·1 bath
Largo • Florida

$ 918,00 USD total por 5 noites

20 – 25 de mar. de 2027

Stylish retreat with heated pool, hot tub, game room, and bright modern interiors
Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach
Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach
Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach
Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach

Seen on HGTV | Heated Pool, Hot Tub• 5 Min Beach

3 bedrooms·2 baths
Largo • Florida
5(17 reviews)

$ 1.055,73 USD total por 3 noites

30 de nov. – 3 de dez. de 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)

$ 1.133,62 USD total por 3 noites

12 – 15 de jun. de 2027

Save Book Thanksgiving Now Special Won't Last Long
Save Book Thanksgiving Now Special Won't Last Long
Save Book Thanksgiving Now Special Won't Last Long
Save Book Thanksgiving Now Special Won't Last Long
Save Book Thanksgiving Now Special Won't Last Long

Save Book Thanksgiving Now Special Won't Last Long

4 bedrooms·3 baths
Clearwater • Florida
4.58(98 reviews)

$ 2.350,00 USD total por 3 noites

8 – 11 de nov. de 2026

Paradise on Parkview Lane
Paradise on Parkview Lane
Paradise on Parkview Lane
Paradise on Parkview Lane
Paradise on Parkview Lane

Paradise on Parkview Lane

3 bedrooms·1 bath
Largo • Florida
5(1 review)

$ 899,00 USD total por 3 noites

3 – 6 de jan. de 2027

A fun outdoor game area for adults and kids alike, featuring putt putt golf, ladder ball, axe throwing, giant Connect 4, and cornhole. Cozy string lights create a welcoming vibe, perfect for family fun, friendly competition, and relaxing evenings.
Florida Vacation Pool Home in Largo
While kids enjoy games like cornhole, adults can relax by the cozy fire pit or gather for an outdoor movie night, creating the perfect balance of fun and relaxation for everyone.
Relax and unwind in the spacious six-person hot tub, perfect for soaking under the open sky after a long day. Designed for comfort and group enjoyment, it’s ideal for couples, families, or friends looking to enjoy a warm, private retreat during their stay.
Florida Vacation Pool Home in Largo

Florida Vacation Pool Home in Largo

3 bedrooms·2 baths
Largo • Florida
5(4 reviews)

$ 1.236,64 USD total por 3 noites

11 – 14 de nov. de 2026

Urban Escape: Artificial Beach W/Volleyball Pit
Urban Escape: Artificial Beach W/Volleyball Pit
Urban Escape: Artificial Beach W/Volleyball Pit
Urban Escape: Artificial Beach W/Volleyball Pit
Urban Escape: Artificial Beach W/Volleyball Pit

Urban Escape: Artificial Beach W/Volleyball Pit

4 bedrooms·3 baths
Clearwater • Florida
4.78(9 reviews)

$ 1.804,00 USD total por 3 noites

19 – 22 de dez. de 2026

Chill & Play: 4br home- Heated Pool, Lanai, Beach! image 1
Chill & Play: 4br home- Heated Pool, Lanai, Beach! image 2
Chill & Play: 4br home- Heated Pool, Lanai, Beach! image 3
We have since added a couple outdoor chairs and a table here
Chill & Play: 4br home- Heated Pool, Lanai, Beach! image 5

Chill & Play: 4br home- Heated Pool, Lanai, Beach!

4 bedrooms·2 baths
Largo • Florida
4.93(45 reviews)

$ 1.047,50 USD total por 3 noites

9 – 12 de nov. de 2026

110 Bath St. Beautiful Gardens
Cottage Apartment on the Bayou image 2
Cottage Apartment on the Bayou image 4
Cottage Apartment on the Bayou image 5
Living Room with wonderful natural light.

Cottage Apartment on the Bayou

2 bedrooms·1 bath
Tarpon Springs • Florida
5(159 reviews)

$ 450,00 USD total por 3 noites

8 – 11 de nov. de 2026

🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴
🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴
🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴
🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴
🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴

🌴Beautiful Pool Home! Beach in 6 min! Sleeps 8 🌴

3 bedrooms·2 baths
Largo • Florida
5(49 reviews)

$ 1.056,85 USD total por 3 noites

8 – 11 de nov. de 2026

110 Bath Street. Cozy Carriage house
CLOSE TO THE BEACH. BEAUTIFUL SUNSETS.
DINING AREA
Reading Area, Office space
DINING AREA/LIVING ROOM

Cozy Carriage House at Spring Bayou

1 bedroom·1 bath
Tarpon Springs • Florida
4.93(170 reviews)

$ 450,00 USD total por 3 noites

8 – 11 de nov. de 2026

Beautiful Historic Home in Tarpon Springs
View of private deck for our guests.
Kitchen fully equiped
Kitchen
Historic House Apartment Tarpon Springs image 6

Historic House Apartment Tarpon Springs

2 bedrooms·1 bath
Tarpon Springs • Florida
4.88(145 reviews)

$ 445,00 USD total por 3 noites

8 – 11 de nov. de 2026

Largo; A Haven of Sun and Fun image 1
Largo; A Haven of Sun and Fun image 2
Welcome!
Living Room
Largo; A Haven of Sun and Fun image 5

Largo; A Haven of Sun and Fun

3 bedrooms·2 baths
Largo • Florida
5(1 review)

$ 1.015,00 USD total por 3 noites

8 – 11 de nov. de 2026

Living room with natural lighting.
Fenced backyard with patio and seating.
Seating area.
Inquire About Discounted Rental Rate
Maxwell Sands

Maxwell Sands

3 bedrooms·2 baths
Indian Rocks Beach • Florida

$ 1.052,65 USD $ 950,01 USD total por 3 noites

8 – 11 de nov. de 2026

Inviting family area with large tv.
Calming entry
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

$ 3.497,71 USD total por 5 noites

8 – 13 de nov. de 2026

Your private backyard oasis—unwind under the stars with a fire and make some s’mores.
Soak under the stars after exploring Florida’s beautiful Gulf Coast.
Spacious fenced backyard with fire pit, lawn games, and lounge seating
Bright, cozy bedroom with warm accents, natural light, and stylish decor
Bright coastal bedroom with cozy decor, soft light, and fresh greenery

Sunshine State of Mind

3 bedrooms·2 baths
Largo • Florida
5(64 reviews)

$ 712,57 USD $ 667,12 USD total por 3 noites

15 – 18 de nov. de 2026

Driftwood Sands #307
Driftwood Sands #307
Driftwood Sands #307
Driftwood Sands #307
Driftwood Sands #307

Driftwood Sands #307

3 bedrooms·2 baths
Indian Rocks Beach • Florida
5(4 reviews)

$ 6.182,23 USD total por 28 noites

30 de nov. – 28 de dez. de 2026