Luxury Vacation Rentals for Large Groups in Clearwater

Luxury Vacation Rentals for Large Groups in Clearwater

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 13 large group vacation rentals – enter your dates for availability.

Top-rated large group vacation rentals in Clearwater

Tropical Tee - Putt Putt - Pool - Hot Tub - Bikes property photo 1

Tropical Tee - Putt Putt - Pool - Hot Tub - Bikes

4 bedrooms•2 baths
1,095 US dollars for 3 nights•
New

~$90 less than other sites

10241 127th Ave N property photo 1

10241 127th Ave N

4 bedrooms•2 baths
881 US dollars for 3 nights•
New

~$75 less than other sites

2 Massive Homes Heated Pool Spa Pickleball GameRm property photo 1

2 Massive Homes Heated Pool Spa Pickleball GameRm

12 bedrooms•11 baths
8,420 US dollars for 3 nights•

~$745 less than other sites

Massive Pool, Spa, Pickle, GameRm property photo 1

Massive Pool, Spa, Pickle, GameRm

12 bedrooms•11 baths
3,206 US dollars for 3 nights•

~$280 less than other sites

Heated Pool, Game Room, Hot Tub property photo 1

Heated Pool, Game Room, Hot Tub

4 bedrooms•3.5 baths
1,184 US dollars for 3 nights•
New

~$100 less than other sites

Heated Pool Pickleball Hot Tub Fire Pit property photo 1

Heated Pool Pickleball Hot Tub Fire Pit

6 bedrooms•3 baths
1,664 US dollars for 3 nights•
New

~$145 less than other sites

Outdoor Movie Theatre, Pool, Putt Putt, Hot Tub property photo 1

Outdoor Movie Theatre, Pool, Putt Putt, Hot Tub

4 bedrooms•2 baths
1,698 US dollars for 3 nights•
New

~$145 less than other sites

Pool, Hot Tub, Putt Putt, Game Room, Karaoke property photo 1

Pool, Hot Tub, Putt Putt, Game Room, Karaoke

4 bedrooms•2 baths
1,102 US dollars for 3 nights•
New

~$95 less than other sites

Welcome to your large group retreat in Clearwater

Welcome to your large group retreat in Clearwater

Bring everyone together on Florida’s Gulf Coast. Our collection of luxury large-group vacation rentals in Clearwater blends hotel polish with the comfort and privacy of a spacious home.
Expect multiple king suites for privacy, flexible bunk rooms, expansive living areas that open to sunny patios, and private pools for easy downtime. Many homes feature chef-worthy kitchens and dining spaces built for celebration, plus ultra fast WiFi, smart work nooks, and parking for several cars. Every stay includes pristine cleaning, inspiring views, and 24/7 concierge service, so coordinating a reunion, friends getaway, or multigenerational trip stays stress free.

Available soon in Clearwater

Tropical Tee - Putt Putt - Pool - Hot Tub - Bikes property photo 1

Tropical Tee - Putt Putt - Pool - Hot Tub - Bikes

4 bedrooms•2 baths
1,095 US dollars for 3 nights•
New

~$90 less than other sites

10241 127th Ave N property photo 1

10241 127th Ave N

4 bedrooms•2 baths
881 US dollars for 3 nights•
New

~$75 less than other sites

Massive Pool, Spa, Pickle, GameRm property photo 1

Massive Pool, Spa, Pickle, GameRm

12 bedrooms•11 baths
3,206 US dollars for 3 nights•

~$280 less than other sites

Heated Pool, Game Room, Hot Tub property photo 1

Heated Pool, Game Room, Hot Tub

4 bedrooms•3.5 baths
1,184 US dollars for 3 nights•
New

~$100 less than other sites

Heated Pool Pickleball Hot Tub Fire Pit property photo 1

Heated Pool Pickleball Hot Tub Fire Pit

6 bedrooms•3 baths
1,664 US dollars for 3 nights•
New

~$145 less than other sites

Outdoor Movie Theatre, Pool, Putt Putt, Hot Tub property photo 1

Outdoor Movie Theatre, Pool, Putt Putt, Hot Tub

4 bedrooms•2 baths
1,698 US dollars for 3 nights•
New

~$145 less than other sites

Pool, Hot Tub, Putt Putt, Game Room, Karaoke property photo 1

Pool, Hot Tub, Putt Putt, Game Room, Karaoke

4 bedrooms•2 baths
1,102 US dollars for 3 nights•
New

~$95 less than other sites

Resort Pool, Spa, Arcade, Mini Golf property photo 1

Resort Pool, Spa, Arcade, Mini Golf

4 bedrooms•2 baths
1,848 US dollars for 3 nights•
New

~$160 less than other sites

Featured large group vacation rentals in Clearwater

2 Massive Homes Heated Pool Spa Pickleball GameRm property photo 1

2 Massive Homes Heated Pool Spa Pickleball GameRm

12 bedrooms•11 baths
8,420 US dollars for 3 nights•

~$745 less than other sites

Massive Pool, Spa, Pickle, GameRm property photo 1

Massive Pool, Spa, Pickle, GameRm

12 bedrooms•11 baths
3,206 US dollars for 3 nights•

~$280 less than other sites

Highlights in Clearwater

Gather your group to experience Clearwater's sun-drenched beaches, vibrant sunset celebrations, and exciting marine adventures perfect for large gatherings.
Clearwater Beach
Pier 60
Clearwater Marine Aquarium
Sand Key Park
BayCare Ballpark
Coachman Park

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Clearwater

Tropical Tee - Putt Putt - Pool - Hot Tub - Bikes property photo 1

Tropical Tee - Putt Putt - Pool - Hot Tub - Bikes

4 bedrooms•2 baths
1,095 US dollars for 3 nights•
New

~$90 less than other sites

10241 127th Ave N property photo 1

10241 127th Ave N

4 bedrooms•2 baths
881 US dollars for 3 nights•
New

~$75 less than other sites

2 Massive Homes Heated Pool Spa Pickleball GameRm property photo 1

2 Massive Homes Heated Pool Spa Pickleball GameRm

12 bedrooms•11 baths
8,420 US dollars for 3 nights•

~$745 less than other sites

Massive Pool, Spa, Pickle, GameRm property photo 1

Massive Pool, Spa, Pickle, GameRm

12 bedrooms•11 baths
3,206 US dollars for 3 nights•

~$280 less than other sites

Heated Pool, Game Room, Hot Tub property photo 1

Heated Pool, Game Room, Hot Tub

4 bedrooms•3.5 baths
1,184 US dollars for 3 nights•
New

~$100 less than other sites

Heated Pool Pickleball Hot Tub Fire Pit property photo 1

Heated Pool Pickleball Hot Tub Fire Pit

6 bedrooms•3 baths
1,664 US dollars for 3 nights•
New

~$145 less than other sites

Outdoor Movie Theatre, Pool, Putt Putt, Hot Tub property photo 1

Outdoor Movie Theatre, Pool, Putt Putt, Hot Tub

4 bedrooms•2 baths
1,698 US dollars for 3 nights•
New

~$145 less than other sites

Pool, Hot Tub, Putt Putt, Game Room, Karaoke property photo 1

Pool, Hot Tub, Putt Putt, Game Room, Karaoke

4 bedrooms•2 baths
1,102 US dollars for 3 nights•
New

~$95 less than other sites

View all homes

Most popular amenities for large group vacation rentals in Clearwater

Outdoor pool (12)
Jacuzzi (8)
Hot tub (8)
Heated pool (1)
Pool table (8)
Beach access (1)
Bbq area (11)
Garden (11)
Dryer (13)
Washer (13)
Fire pit (1)
Oven (13)
Hammock (1)
Kitchen (13)
Patio (1)
Tv (13)

More popular large group destinations near Clearwater

Large group vacation rentals in Clearwater Beach
Large group vacation rentals in Seminole
Large group vacation rentals in St. Petersburg
Large group vacation rentals in St. Pete Beach
Large group vacation rentals in Tampa
Large group vacation rentals in Cortez
Large group vacation rentals in Bradenton Beach
Large group vacation rentals in Siesta Key

Other popular amenities & vacation types in Clearwater

Family vacation rentals in Clearwater
Pet-friendly vacation rentals in Clearwater
Hot tub vacation rentals in Clearwater
Discover more large groups activities in Clearwater

Discover more large groups activities in Clearwater

Clearwater shines with powder-soft sand and calm, emerald water. Clearwater Beach’s wide shoreline invites lingering days by the surf, while Pier 60’s nightly sunset celebration brings live performers and a golden horizon.
Take a ferry to nearby Caladesi Island State Park for unspoiled shores and shelling, book a dolphin cruise on the Intracoastal, or paddle through tranquil mangroves. Baseball fans can catch spring action at BayCare Ballpark, and art lovers are close to St. Petersburg’s acclaimed museums. With year-round warmth and a relaxed coastal rhythm, this is why Wander’s luxury vacation rentals in Clearwater are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Clearwater

Why should I book a Wander in Clearwater over other large group vacation rentals?

Wander offers a level of consistency and quality you won’t find with most large group vacation rentals.
Every home in Clearwater delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular large group vacation rentals in Clearwater?

Some of our most popular large group vacation rentals in Clearwater include Tropical Tee - Putt Putt - Pool - Hot Tub - Bikes, 10241 127th Ave N, and 2 Massive Homes Heated Pool Spa Pickleball GameRm. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different large group vacation rentals does Wander have available in Clearwater?

Wander offers 13 large group vacation rentals in Clearwater, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s large group vacation rentals in Clearwater?

You can check-in to Wander large group vacation rentals in Clearwater after 4.00pm and check-out before 10.00am.

Do Wander’s large group vacation rentals in Clearwater have WiFi access?

Yes. Every Wander home in Clearwater has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.