Location

Dates

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Vacation rentals in Treasure Island, Florida, United States

#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

$3,627.68 USD total for 3 nights

Nov 7 – 10, 2026

Bright open dining space with seating for 6 and stylish modern lighting

Bayshore Beautiful Home | 4BR + Gym + Studio

Covered patio with comfy seating and a private, lush fenced yard

Bayshore Beautiful Home | 4BR + Gym + Studio

Bright open living area with dining space, bar seating, and large TV

Bayshore Beautiful Home | 4BR + Gym + Studio

5 bedrooms·3 baths

Tampa • Florida

$6,480.00 USD total for 30 nights

Nov 30 – Dec 30, 2026

The open floor plan features an 8-foot island, connecting the gourmet kitchen, living, and dining areas. Surrounded by palm and oak trees, large windows offer views of nature w french doors leading to the outdoor deck and fully enclosed backyard

Bright dining area with seating for 8, surrounded by large windows and French doors overlooking the property’s tropical greenery. Perfect for family dinners, morning coffee, or gathering after a day in Tampa Bay.

Modern Luxury | Fenced | Pet Friendly

The living area with seating for eight, has views of the private garden set amongst oak trees, palm trees, birds of paradise making it the perfect place to relax and unwind or connect with friends and family. The sofa features a pull out queen bed.

Guest Room Featuring a Queen bed, smart TV & dedicated workspace

Modern Luxury | Fenced | Pet Friendly

3 bedrooms·2½ baths

Tampa • Florida

5(1 review)

$854.55 USD total for 3 nights

Nov 29 – Dec 2, 2026

Beautiful elevated home with private yard

Welcome to Rollin' with the Waves

Only five houses to the sand

Your tropical getaway awaits

Rollin' with the Waves

3 bedrooms·2½ baths

Holmes Beach • Florida

5(2 reviews)

$2,954.67 USD total for 7 nights

Nov 27 – Dec 4, 2026

Float the afternoon away

Welcome to Under the Foxtails

Bright, open coastal living space

Stylish space to relax and chat

Under the Foxtails

3 bedrooms·3 baths

Holmes Beach • Florida

$1,960.14 USD total for 7 nights

Nov 7 – 14, 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

Pompano Palms

3 bedrooms·3½ baths

Palmetto • Florida

$71/ night(excl. fees & taxes)

Welcome to AMI Villa

Light up the night!

Spectacular night lights over the pool

Amazing rooftop screened in patio

Comfortable family-style living area

AMI Villa

3 bedrooms·3 baths

Holmes Beach • Florida

5(3 reviews)

$3,113.45 USD total for 7 nights

Nov 30 – Dec 7, 2026

Relax by the fire pit and enjoy sunset views in this private backyard

Let the kids play putt putt golf, bocce ball and more while you relax in the refreshing pool. Summertime paradise awaits!

The Salty Palm

3 bedrooms·2 baths

Bradenton • Florida

5(43 reviews)

$1,052.56 USD total for 3 nights

Nov 7 – 10, 2026

Gulf Drive Living

Gulf Drive Living

Gulf Drive Living

Gulf Drive Living

Gulf Drive Living

Gulf Drive Living

2 bedrooms·1 bath

Holmes Beach • Florida

$3,150.00 USD total for 7 nights

Nov 7 – 14, 2026

Your Tampa Bay Vacation Entertainment Home image 1

Entertainment Awaits 3-Bedrooms, 2-Full Bath, Washer & Dryer, 8Ft Pool, Poker, & PingPong Table, Dart-broad, Grill, 900Sq. Ft. Lanai, with Privacy Fence. Smart TV in Every-room.
Just Bring Your Clothes & Food!

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Your Tampa Bay Vacation Entertainment Home image 5

Your Tampa Bay Vacation Entertainment Home

3 bedrooms·2 baths

Tampa • Florida

4.79(180 reviews)

$784.00 USD total for 6 nights

Nov 7 – 13, 2026

Poolside meets game time

From the heated pool and hot tub to the game courts, fire pit, and outdoor lounging areas—our backyard is designed for the ultimate getaway experience.

Soak in the hot tub before or after a refreshing dip in the pool—perfect for relaxing mornings, sunset wind-downs, or starlit evenings.

The ultimate bunk room & play space! Featuring 6 queen-size bunk beds, this fun-filled room is perfect for kids, teens, and groups to sleep, play, and make unforgettable memories together.

Enjoy our spacious mini golf course—perfect for friendly competition, family fun, and laid-back afternoons right at the property.

7mi to AMI w/ Pickleball+Golf | Htd Pool+Tiki Hut

5 bedrooms·3 baths

Bradenton • Florida

$2,849.89 USD total for 3 nights

Nov 13 – 16, 2026

Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

4 bedrooms·3 baths

Bradenton • Florida

5(22 reviews)

$3,390.24 USD total for 5 nights

Nov 7 – 12, 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

Relax and unwind in the covered seating area next to the pool, with comfortable outdoor furniture and a dining table

The incredible outdoor space truly sets this home apart.The new saltwater pool with a spa and sunshelf were completed in spring 2023.

Guests love that the living room flows directly out to the pool and lanai!

The kitchen includes a backsplash made of real shells, floating driftwood shelves made by a local artist, granite countertops, and all the appliances and accessories you will need.

The primary bedroom has a king bed, armoire and dresser for clothing storage, and direct access to the swimming pool.

Palma Janoli

3 bedrooms·2 baths

Bradenton • Florida

5(110 reviews)

$1,072.29 USD total for 3 nights

Dec 1 – 4, 2026

Palma Rosa and Palma Janoli

The incredible outdoor space truly sets this home apart.The new saltwater pool with a spa and sunshelf were completed in spring 2023.

Palma Rosa's outdoor space includes a covered outdoor seating/dining area with an outdoor TV

Easily walk between the two houses.

Relax and unwind in the covered seating area next to the pool, with comfortable outdoor furniture and a dining table

Palma Rosa and Palma Janoli

6 bedrooms·4 baths

Bradenton • Florida

$6,023.86 USD total for 3 nights

Dec 26 – 29, 2026

Guests love the outdoor space of this home, which includes a heated pool, covered seating area with a Roku TV, outdoor dining space and mural. Everything is screened so bugs and tropical wildl

The home has a large heated pool, with new paver deck and new pool cage!

The garage of the home has foosball, darts, and a pingpong table. There are beach chairs, toys, and umbrellas available for guests to use.

Enjoy a movie night after a day at the beach! The living room has a large cozy sectional, tv, and fireplace.

The primary bedroom flows right out to the pool!

Palma Rosa

3 bedrooms·2 baths

Bradenton • Florida

5(41 reviews)

$1,073.57 USD total for 3 nights

Nov 13 – 16, 2026

Relax after a day of taking in the sight around Tampa Bay.

Modern living, dining gathering space.

Walk, roller blade, job or rent a bike with city bike share program, all steps away.

Fully stocked Keurig machine and open kitchen greet you each morning.

The place where everyone ends up gathering!

Bayshore • South Tampa Luxury: Private Bath

2 bedrooms·1 bath

Tampa • Florida

4.93(43 reviews)

$54,982.00 USD total for 120 nights

Nov 7, 2026 – Mar 7, 2027

Coastal Palm Hideaway

Coastal Palm Hideaway

Coastal Palm Hideaway

Coastal Palm Hideaway

Coastal Palm Hideaway

Coastal Palm Hideaway

4 bedrooms·2 baths

Bradenton • Florida

4.92(62 reviews)

$835.07 USD total for 3 nights

Dec 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

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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

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

South Tampa Retreat | Pool, King Bed & Jacuzzi Tub

South Tampa Retreat | Pool, King Bed & Jacuzzi Tub

South Tampa Retreat | Pool, King Bed & Jacuzzi Tub

South Tampa Retreat | Pool, King Bed & Jacuzzi Tub

2 bedrooms·1 bath

Tampa • Florida

$1,222.97 USD total for 7 nights

Nov 7 – 14, 2026

Furnished 2BR Corporate Apartment in South Tampa | Pool, Parking

Furnished 2BR Corporate Apartment in South Tampa | Pool, Parking

Furnished 2BR Corporate Apartment in South Tampa | Pool, Parking

Furnished 2BR Corporate Apartment in South Tampa | Pool, Parking

2 bedrooms·1 bath

Tampa • Florida

$1,170.83 USD total for 7 nights

Nov 7 – 14, 2026