Location

Dates

Guests

Vacation rentals in Clearwater, Florida, United States

Pond-side ART-home with private pool. DOGS WELCOME

5 bedrooms·3 baths

Pinellas Park • Florida

5(20 reviews)

$318/ night(excl. fees & taxes)

Dive into vacation mode with a sunny pool and playful float.

Resort-style St. Pete retreat with pool, game room & outdoor dining

Gather around the waterfront fire-pit seating area.

Tiki-style backyard bar with TV, ambient lighting, and private patio seating

Make game night a highlight of your stay with the foosball table.

2 Homes - 4 MN to Madiera BCH - Hottub - HTD Pool

7 bedrooms·6 baths

St. Petersburg • Florida

$2,600.00 USD total for 3 nights

Nov 11 – 14, 2026

Beautiful 1BR Condo only steps to the water & fun! image 8

Beautiful 1BR Condo only steps to the water & fun! image 5

Beautiful 1BR Condo only steps to the water & fun! image 55

Beautiful 1BR Condo only steps to the water & fun! image 3

Welcome to beautiful North Redington Beach, FL.

No Cleaning Fee, 0min to Beach, 1BR w/ parking

1 bedroom·1 bath

North Redington Beach • Florida

5(46 reviews)

$720.60 USD total for 4 nights

Nov 7 – 11, 2026

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

2 bedrooms·2 baths

Walton County • Florida

5(12 reviews)

$739.50 USD total for 3 nights

Nov 7 – 10, 2026

Beach Living & Shuffleboard

16100 2nd St - Web Quality (4)

Full-Equipped Kitchen for making family meals

16100 2nd St - Web Quality (22)

She's A Shore Thing

3 bedrooms·2 baths

Redington Beach • Florida

$1,127.56 USD $1,015.58 USD total for 3 nights

Nov 7 – 10, 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)

$1,135.76 USD total for 3 nights

Jun 12 – 15, 2027

Property grounds

Private kitchen

Beachfront Condo at La Contessa!, 3BD/3BA, Poolside Cabana, Private Fishing Pier

3 bedrooms·3 baths

Redington Beach • Florida

5(12 reviews)

$11,215.25 USD total for 30 nights

Nov 15 – Dec 15, 2026

Jacuzzi/ Pool #1

Vibrant 2BR/2BA w/ King Bed | Pool, Gym #11

2 bedrooms·2 baths

Tampa • Florida

5(10 reviews)

$673.48 USD $621.39 USD total for 3 nights

Nov 7 – 10, 2026

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

1 bedroom·1 bath

Madeira Beach • Florida

$607.00 USD total for 3 nights

Nov 7 – 10, 2026

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

1 bedroom·1 bath

Madeira Beach • Florida

$607.00 USD total for 3 nights

Nov 7 – 10, 2026

Jacuzzi/ Pool #1

Modern 2BR | Pool, Gym + Pet-Friendly #12

2 bedrooms·2 baths

Tampa • Florida

5(2 reviews)

$705.12 USD $649.86 USD total for 3 nights

Nov 10 – 13, 2026

59-web-or-mls-12310 Memorial Hwy-74.jpg

71-web-or-mls-12310 Memorial Hwy-70.jpg

54-web-or-mls-12310 Memorial Hwy-51.jpg

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 nights

Nov 7 – 14, 2026

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

#1 Largest Tampa Private Compound · 13BR Sleeps 40+ · Heated Pool/Spa

13 bedrooms·7 baths

Tampa • Florida

$9,384.48 USD total for 3 nights

Nov 7 – 10, 2026

Casa Noir by Perez Benitez image 1

Casa Noir by Perez Benitez image 2

Casa Noir by Perez Benitez image 3

Casa Noir by Perez Benitez image 4

Casa Noir by Perez Benitez image 5

Casa Noir by Perez Benitez

4 bedrooms·2 baths

St. Petersburg • Florida

5(6 reviews)

$300/ night(excl. fees & taxes)

Private screened pool with lounge chairs and easy indoor-outdoor access

Primary bedroom — king bed with coastal luxury bedding, wall-mounted smart TV, and direct sliding glass door access to the private screened pool.

Coastal dining room at Sun Oasis — a farmhouse-style table set for six with blue place settings and teal glassware, teal front door visible beyond, flowing into the living room.

Full living room — two plush sofas, striped armchair, coastal round ottoman, oversized Oasis on 40th turtle 70-inch TV art, guest book on the coffee table, and the game room archway beyond.

Screened private pool with string lights for relaxing evening swims

Sun Oasis Heated Pool Game Room and Wood Fire Pit Near St Pete Beaches

3 bedrooms·2 baths

St. Petersburg • Florida

5(72 reviews)

$685.78 USD total for 3 nights

Nov 15 – 18, 2026

Elegant dinning room overlooking Lanai into the pool deck.

Kayaks, putting green, heated pool, fire pit, enclosed lanai with extended seating underneath the gazebo.

Waterfront Access, Heated Pool, Mini Golf & Kayaks

Waterfront Access, Heated Pool, Mini Golf & Kayaks

Waterfront Access, Heated Pool, Mini Golf & Kayaks

5 bedrooms·3 baths

Tampa • Florida

4.77(43 reviews)

$2,719.84 USD total for 3 nights

Nov 11 – 14, 2026

SeaBreeze 101-Sunsets, sand, pool! Free parking

SeaBreeze 101-Sunsets, sand, pool! Free parking

SeaBreeze 101-Sunsets, sand, pool! Free parking

SeaBreeze 101-Sunsets, sand, pool! Free parking

SeaBreeze 101-Sunsets, sand, pool! Free parking

SeaBreeze 101-Sunsets, sand, pool! Free parking

2 bedrooms·2 baths

Madeira Beach • Florida

5(31 reviews)

$1,180.85 USD total for 3 nights

Nov 14 – 17, 2026

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

4 bedrooms·2 baths

St. Petersburg • Florida

4.95(43 reviews)

$8,476.00 USD total for 30 nights

Nov 7 – Dec 7, 2026

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

7 bedrooms·7 baths

Madeira Beach • Florida

$5,905.38 USD total for 3 nights

Nov 7 – 10, 2026

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

2 bedrooms·2 baths

Madeira Beach • Florida

$1,850.05 USD total for 3 nights

Nov 7 – 10, 2026

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath

Madeira Beach • Florida

$1,643.48 USD total for 3 nights

Nov 7 – 10, 2026

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath

Madeira Beach • Florida

$1,543.60 USD total for 3 nights

Nov 7 – 10, 2026

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

1 bedroom·1 bath

Madeira Beach • Florida

$1,492.53 USD total for 3 nights

Nov 7 – 10, 2026

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

1 bedroom·1 bath

Madeira Beach • Florida

$1,543.60 USD total for 3 nights

Nov 7 – 10, 2026