Location

Dates

Guests

Vacation rentals in Clearwater, Florida, United States

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

$194 – $593/ night(excl. fees & taxes)

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 nights

Feb 21 – 24, 2027

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

$587.00 USD total for 3 nights

Sep 23 – 26, 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

$587.00 USD total for 3 nights

Sep 23 – 26, 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 nights

Sep 23 – 30, 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

$8,470.56 USD total for 3 nights

Sep 23 – 26, 2026

Casa Noir by Perez Benitez image 1

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Casa Noir by Perez Benitez image 5

Casa Noir by Perez Benitez

4 bedrooms·2 baths

St. Petersburg • Florida

5(6 reviews)

$200 – $240/ night(excl. fees & taxes)

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 | Game Room, Pool, Fire Pit | Near Beach

3 bedrooms·2 baths

St. Petersburg • Florida

5(72 reviews)

$202 – $539/ night(excl. fees & taxes)

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

Sep 23 – 26, 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)

$1,293.00 USD total for 7 nights

Sep 23 – 30, 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

$5,301.96 USD total for 3 nights

Sep 23 – 26, 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

$1,803.52 USD total for 3 nights

Sep 23 – 26, 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

$1,465.29 USD total for 3 nights

Sep 23 – 26, 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

$1,615.11 USD total for 3 nights

Sep 23 – 26, 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

$1,517.50 USD total for 3 nights

Sep 23 – 26, 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

$1,517.50 USD total for 3 nights

Sep 23 – 26, 2026

Have an amazing experience with family and friends in this magnificent property! Make memories while enjoying the beautiful nature and having a dip in this immaculate pool. Inquire now!

Imperial Oasis

4 bedrooms·3 baths

Tampa • Florida

5(28 reviews)

$2,874.68 USD $2,752.21 USD total for 6 nights

Oct 25 – 31, 2026

Common Area: 🌳 Spacious Outdoor w/ table and chairs

Welcome to your perfect retreat—ideal for a solo traveler or couple.

St. Petersburg, Florida – a vibrant city bursting with sunshine, culture, and endless possibilities! Nestled on the Gulf Coast, St. Pete is a haven for art lovers, outdoor enthusiasts, and those seeking a laid-back coastal escape

A beautifully remodeled bathroom guests love.

Step outside to your private outdoor deck, complete with a dining table and chairs—perfect for morning coffee or alfresco meals in the fresh air.

Private Deck • Pet Friendly • Spacious Courtyard

0 bedrooms·1 bath

St. Petersburg • Florida

$454.26 USD total for 3 nights

Sep 23 – 26, 2026

Common Area: 🌳 Spacious Outdoor w/ table and chairs

Private Deck • Pet Friendly • Spacious Courtyard

Private Deck • Pet Friendly • Spacious Courtyard

Private Deck • Pet Friendly • Spacious Courtyard

Private Deck • Pet Friendly • Spacious Courtyard

0 bedrooms·1 bath

St. Petersburg • Florida

$487.03 USD total for 3 nights

Sep 23 – 26, 2026

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 nights

Sep 23 – 28, 2026

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 nights

Sep 30 – Oct 4, 2026

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 1

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 2

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 4

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 5

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 6

1Bedroom/ 10 mins to Downtown Saint Peterburg

1 bedroom·1 bath

St. Petersburg • Florida

4.36(25 reviews)

$85 – $95/ night(excl. fees & taxes)

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

0 bedrooms·1 bath

St. Petersburg • Florida

4.32(19 reviews)

$316.00 USD total for 3 nights

Sep 23 – 26, 2026

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Magnolia near the beach and downtown St. Pete image 3

Magnolia near the beach and downtown St. Pete image 4

Magnolia near the beach and downtown St. Pete image 5

Magnolia near the beach and downtown St. Pete

5 bedrooms·3 baths

St. Petersburg • Florida

4.85(150 reviews)

$149 – $561/ night(excl. fees & taxes)