
Luxury Vacation Rentals for Large Groups in Anna Maria
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 10 large group vacation rentals – enter your dates for availability.

Welcome to your large group retreat in Anna Maria
Bring everyone together at our luxury vacation rentals in Anna Maria, designed for memorable group stays without the stress. Wander pairs the polish of a five-star hotel with the comfort of a private home, so big gatherings feel effortless from arrival to checkout.
Think generous bedroom suites and flexible sleeping setups, expansive kitchens ready for crowd-sized meals, and indoor-outdoor living for lingering poolside or reconnecting across multiple lounge areas. Each home is professionally cleaned, thoughtfully outfitted, and supported by 24/7 concierge service, with ultra fast WiFi for teams or blended trips. For reunions, milestone celebrations, or corporate retreats, your group will finally have space to breathe.
Highlights in Anna Maria
Gather your crew for a memorable island getaway featuring spacious beaches, historic piers, and charming local shops perfect for group exploration.
Bean Point Beach
Anna Maria City Pier
Pine Avenue
Bayfront Park
Rod and Reel Pier
Coquina Beach
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.
All homes in Anna Maria

Anna Maria, FL
Wander Anna Maria Canalfront
$9,355 for 6 nights•
New
5 bedrooms•5 beds•5 baths

Anna Maria, FL
Wander Anna Maria Oasis
$5,772 for 6 nights•
New
5 bedrooms•5 beds•4 baths

Anna Maria, FL
Wander Anna Maria Allure
$4,798 for 6 nights•
New
5 bedrooms•5 beds•4 baths

Anna Maria, FL
Wander Anna Maria Bluffs
$5,756 for 6 nights•
New
7 bedrooms•7 beds•3 baths

Anna Maria, FL
Wander Anna Maria Bay
$13,140 for 6 nights•
New
7 bedrooms•7 beds•8 baths

Anna Maria, FL
Wander Anna Maria Escape
$6,068 for 6 nights•
New
5 bedrooms•5 beds•7 baths

Holmes Beach, FL
Wander Anna Maria Cove
$7,560 for 6 nights•
New
7 bedrooms•7 beds•7 baths

Anna Maria, FL
Wander Anna Maria Sea
$1,562 for 2 nights•
New
4 bedrooms•4 beds•5 baths
Most popular amenities for large group vacation rentals in Anna Maria
More popular large group destinations near Anna Maria
Other popular amenities & vacation types in Anna Maria

Discover more large groups activities in Anna Maria
Powder-soft sand, clear Gulf shallows, and pastel cottages set a laid-back tone in Anna Maria at the serene north end of the island. Strict height limits keep the skyline low and the stars bright, while gentle surf and wide beaches make unhurried days the norm.
Stroll Pine Avenue’s boutiques and galleries, watch dolphins crest near the piers, or bike to Bean Point for sunset over Egmont Key and the Sunshine Skyway in the distance. Nature preserves, sea turtle nesting season, and a breezy island trolley add easygoing charm without the crowds. This is why Wander's luxury vacation rentals in Anna Maria are the perfect choice, whether you're traveling for work or leisure.
FAQs: Vacation Rentals in Anna Maria
Why should I book a Wander in Anna Maria 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 Anna Maria 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 Anna Maria?
Some of our most popular large group vacation rentals in Anna Maria include Wander Anna Maria Bay, Wander Anna Maria Allure, and Wander Anna Maria Escape. 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 Anna Maria?
Wander offers 10 large group vacation rentals in Anna Maria, 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 Anna Maria?
You can check-in to Wander large group vacation rentals in Anna Maria after 4.00pm and check-out before 10.00am.
Do Wander’s large group vacation rentals in Anna Maria have WiFi access?
Yes. Every Wander home in Anna Maria 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.



























































































