Best Vacation Homes in Anna Maria
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
1050 ft²
Private Pool
Fireplace/Heating
Pool
Ocean View
AU $1,472/Night
7 Nights - AU $10,304
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
538.2 ft²
- Fireplace/Heating
Pet Friendly
Parking
Internet
AU $290/Night
7 Nights - AU $2,033
House
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace
Kitchen- Parking
AU $506/Night
7 Nights - AU $3,544
New
House
6 Bedrooms
6 Baths
12 Guests
3700 ft²
- Private Pool
Oceanfront
Hot Tub- Fireplace/Heating
AU $3,724/Night
7 Nights - AU $26,068
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
1625.35 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
View
AU $705/Night
7 Nights - AU $4,938
New
House
5 Bedrooms
5 Baths
8 Guests
3948 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $2,760/Night
7 Nights - AU $19,320
New
House
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $1,907/Night
7 Nights - AU $13,351
New
House
4 Bedrooms
3 Baths
8 Guests
2468 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $1,905/Night
7 Nights - AU $13,332
Anna Maria Luxury Rentals
AU $9,128/Night
7 Nights - AU $63,895
House
9.5(4 Reviews)
4 Bedrooms
4 Baths
8 Guests
2002.09 ft²
- Oceanfront
- Ocean View
- View
- Parking
AU $7,367/Night
7 Nights - AU $51,570
House
10.0(62 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $6,738/Night
7 Nights - AU $47,169
House
1 Bedroom
5 Baths
8 Guests
3218.41 ft²
- Oceanfront
- Hot Tub
Spa- Fireplace/Heating
AU $6,580/Night
7 Nights - AU $46,058
House
9.4(6 Reviews)
4 Bedrooms
4 Baths
8 Guests
2850 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $5,436/Night
7 Nights - AU $38,051
House
9.6(4 Reviews)
6 Bedrooms
6 Baths
12 Guests
5500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $5,431/Night
7 Nights - AU $38,018
House
10.0(2 Reviews)
4 Bedrooms
7 Baths
8 Guests
5251 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
AU $5,292/Night
7 Nights - AU $37,044
House
10.0(35 Reviews)
5 Bedrooms
5 Baths
8 Guests
2582 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $4,956/Night
7 Nights - AU $34,690
Anna Maria Pet Friendly Vacation Rentals
New
House
6 Bedrooms
5 Baths
10 Guests
2714 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $1,836/Night
7 Nights - AU $12,852
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
2260.42 ft²
- Pet Friendly
- Parking
- Internet
Child Friendly
AU $1,286/Night
7 Nights - AU $9,004
Villa
1 Bedroom
1 Bath
- Oceanfront
- Ocean View
- View
- Pet Friendly
AU $307/Night
7 Nights - AU $2,149
House
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $768/Night
7 Nights - AU $5,373
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1571.53 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
AU $938/Night
7 Nights - AU $6,564
Cottage
10.0(304 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $855/Night
7 Nights - AU $5,988
House
10.0(173 Reviews)
2 Bedrooms
2 Baths
4 Guests
962 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $471/Night
7 Nights - AU $3,299
House
10.0(97 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
AU $801/Night
7 Nights - AU $5,607
Anna Maria Large Vacation Homes
Villa
10.0(123 Reviews)
2 Bedrooms
1 Bath
4 Guests
749 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $566/Night
7 Nights - AU $3,960
House
10.0(1 Review)
5 Bedrooms
4 Baths
10 Guests
2970.84 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
AU $2,755/Night
7 Nights - AU $19,286
Villa
1.0(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Pool
- Pet Friendly
- Kitchen
AU $965/Night
7 Nights - AU $6,758
Villa
10.0(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
966 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $693/Night
7 Nights - AU $4,853
House
10.0(1 Review)
4 Bedrooms
3 Baths
12 Guests
1345.49 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
AU $1,470/Night
7 Nights - AU $10,292
Villa
9.8(116 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $591/Night
7 Nights - AU $4,140
Villa
9.6(55 Reviews)
2 Bedrooms
1 Bath
6 Guests
700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $889/Night
7 Nights - AU $6,220
Villa
9.6(41 Reviews)
1 Bedroom
2 Baths
6 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
AU $668/Night
7 Nights - AU $4,672
Why Choose Rent By Owner for your Anna Maria Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Anna Maria Vacation Rentals
Where are the best neighborhoods to stay in Anna Maria?
When planning your stay in Anna Maria, Florida, exploring the different neighborhoods can help you find the perfect setting for your vacation. Whether you prefer a tranquil area close to pristine beaches or a lively community with convenient access to local amenities, each neighborhood offers its own unique charm. By choosing the right location within Anna Maria, you can enhance your experience and enjoy a relaxing getaway tailored to your preferences. Discover the ideal neighborhood that suits your style and makes your stay truly memorable.
Key Royale
Situated in this charming area, you can enjoy peaceful surroundings and easy access to the scenic beauty of Anna Maria Island. It's an ideal spot for those seeking a tranquil retreat with convenient proximity to waterfront activities.
View 4940+ Rentals in Key RoyaleBest Times to Visit Anna Maria
When should you plan your Vacation Rentals stay?
Choosing the best time to visit this charming destination depends on your preferences for weather, crowd levels, and regional events, ensuring you can enjoy the area's beautiful beaches and relaxed atmosphere at its most appealing.
Peak Season Highlights
Spring (March to May)
During spring, the weather warms up, making it an ideal time for beach activities and exploring the area’s natural beauty.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Winter Holidays (December to February)
This peak period offers pleasant temperatures and holiday festivities, attracting visitors seeking a warm getaway in the region.
Average Temperature Daytime: 68°F to 75°F - Nighttime: 55°F to 65°F
Off-Season Highlights
Summer (June to August)
In summer, you can enjoy quieter beaches and lower rates, though be prepared for hotter days and humidity in this destination.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 75°F to 80°F
Fall (September to November)
Fall sees fewer visitors, offering more tranquil surroundings and better deals on accommodations across the region.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F
Weekly Weather Forecast for Anna Maria
How to Book Your Anna Maria Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Anna Maria
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for sunset dinners in this charming coastal destination.
- Relax by a private or shared pool, ideal for cooling off after a day at the nearby beaches.
- Benefit from lush landscaped gardens that add to the tranquility of your stay.
- Make use of spacious patios or decks for lounging and soaking up the sunshine.
- Experience the convenience of outdoor showers, especially useful after beach excursions.
- Take advantage of boat docks or waterfront access to explore the region by water.
- Utilize shaded lanai areas or verandas to unwind while enjoying scenic views of the area’s natural beauty.
Top Attractions Around Anna Maria
What attractions are nearby?
Enjoy a variety of nearby activities in Anna Maria, Florida, where you can explore beautiful beaches, indulge in water sports, or take leisurely strolls along scenic coastlines—making your stay here truly memorable.
Family Activities
- Anna Maria Island Beach:** Experience the pristine sands and gentle waves that make this beach a perfect family-friendly spot for swimming, sunbathing, and building sandcastles.
- Anna Maria City Pier:** Enjoy fishing, strolling along the pier, or simply taking in scenic views that showcase the natural beauty of this coastal region with your loved ones.
- Bean Point:** Discover tranquil Picnicking opportunities and breathtaking sunset vistas at one of the area's most iconic and family-oriented outdoor locations.
- Holmes Beach Marina:** Embark on boat rentals or guided eco-tours that provide memorable adventures and educational experiences suitable for all ages in this charming seaside community.
Adult Activities
- Sunset Cruises: Embark on an evening cruise along the coastline to enjoy breathtaking sunsets and the tranquil waters surrounding this charming destination.
- Fishing Charters: Experience a day of deep-sea or bay fishing with guided charters that cater to both beginners and seasoned anglers here in the region.
- Beachcombing and Shelling: Spend your days strolling along the pristine beaches, collecting unique shells and soaking up the sun on this inviting barrier island.
- Kayaking Adventures: Explore calm waters and scenic mangroves by renting a kayak, offering a peaceful way to connect with nature here in the area.
Other Places to Stay in Anna Maria, FL
Island Players
Anna Maria Island Museum and Historical Park
AMI Outfitters Coastal Gear & Apparel
Historic Green Village
Anna Maria City Pier
Bayfront Park
Anna Maria Beach
Anna Maria Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Research upcoming festivals and community gatherings to enhance your experience and enjoy the vibrant atmosphere here.
- Explore the Beaches Early: Visiting the area’s scenic beaches during the early morning hours allows you to unwind peacefully before the crowds arrive.
- Discover Unique Dining Spots: Take time to sample local eateries and waterfront cafes, which showcase the region’s fresh seafood and charming ambiance.
- Utilize Water Transportation: Make the most of boat rentals or water taxis to explore nearby islands and coastal areas, adding an adventurous touch to your stay here.
Transportation Options
- Personal Vehicles: Renting or driving your own car provides the most flexibility for exploring Anna Maria and enjoying its scenic coastal areas.
- Local Trolleys and Shuttles: Public transportation options like trolleys operate seasonally, offering a convenient way to travel around the region without worrying about parking.
- Bike Rentals: Cycling is an eco-friendly and popular choice here, allowing you to easily navigate the area’s bike paths while soaking in the seaside scenery.
- Taxi and Rideshare Services: App-based services like Uber and Lyft are readily available for quick, hassle-free transportation within Anna Maria and nearby spots.
Local Customs Options
- Respect for Beach Regulations: You’ll find that following local beach rules, such as designated swimming areas and glass bottle bans, helps preserve the pristine beauty of this coastal destination.
- Mindful Tipping Customs: Tipping service staff at local restaurants and cafes here is customary, reflecting the welcoming and friendly spirit of the community.
- Local Arts Appreciation: Supporting regional artists by visiting galleries or participating in cultural events allows you to embrace the vibrant artistic traditions of this area.
- Environmental Conservation Attitudes: Engaging in eco-friendly practices, like avoiding littering and using reusable items, aligns with the region’s commitment to preserving its natural surroundings.
Frequently Asked Questions About Anna Maria?
1. What are the top vacation rentals in Anna Maria?
There are a lot of options in Anna Maria. If you plan on staying in the Anna Maria area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Anna Maria:
- Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
- Beautiful, Gulf-Front Home on Bean Point-Halcyon House
- Cozy Cottage w private Beach Access,AC&WiFi -Quiet North End AMI. Tropical Oasis
- BEACH NEST IS GETTING A RENOVATION! WE WILL BE BACK! CHECK BACK FOR UPDATES! XOX
- Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
- Dragonfly - Southern charm on the North end of Anna Maria Island
- Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point.
- 2nd House from the Beach with No Roads to Cross
- Anna Maria Island Rentals - Beach Front - "Angels Envy" -Rod & Reel Pier Retreat
- Charming House with Private Heated Pool, Lanai. Great location to beach & shops
2. How many vacation rentals have private pools in Anna Maria?
There are 885 vacation rentals with private pools near Anna Maria. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Anna Maria are best for families?
If you are looking for a family-friendly vacation home in Anna Maria, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Anna Maria:
4. How many Rentbyowner vacation rentals are available in Anna Maria?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1632 in the Anna Maria area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Anna Maria.
5. What is the cancellation policy for vacation rentals in Anna Maria, Florida?
Cancellation policies vary depending on the specific property listing. You should review the cancellation terms outlined in the listing details or contact the property owner directly for clarification.
6. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning fees, service charges, or taxes are typically listed on the property page. Always check the detailed booking information or reach out to the host for a complete understanding of all costs involved.
7. Is it possible to modify or cancel my reservation if my plans change?
Modifications and cancellations depend on the property's individual policy. You are encouraged to read the specific cancellation and modification policies listed with your chosen vacation rental or contact the owner for assistance.
8. What amenities are included in the vacation rentals here?
The amenities offered vary by property. To ensure the rental meets your needs, review the amenities section on each listing, or inquire directly with the owner for more detailed information.
9. How do I ensure my stay complies with local rules and regulations?
You should carefully review the house rules and local guidelines provided in the listing description. For additional questions, contacting the property owner or local authorities can help ensure a smooth and compliant stay.
Anna Maria Top Rated Vacation Rentals
House
10.0(200 Reviews)
4 Bedrooms
1 Bath
8 Guests
2800 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $498/Night
7 Nights - AU $3,483
House
10.0(190 Reviews)
5 Bedrooms
3 Baths
8 Guests
2884 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $1,883/Night
7 Nights - AU $13,184
House
10.0(172 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $698/Night
7 Nights - AU $4,884
House
10.0(153 Reviews)
2 Bedrooms
2 Baths
6 Guests
1510 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $698/Night
7 Nights - AU $4,884
House
10.0(151 Reviews)
4 Bedrooms
4 Baths
8 Guests
43056 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $1,557/Night
7 Nights - AU $10,902
House
10.0(143 Reviews)
5 Bedrooms
5 Baths
8 Guests
3500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $3,897/Night
7 Nights - AU $27,278
House
10.0(143 Reviews)
2 Bedrooms
1 Bath
6 Guests
749 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $672/Night
7 Nights - AU $4,704
House
10.0(140 Reviews)
5 Bedrooms
3 Baths
10 Guests
2400 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $2,186/Night
7 Nights - AU $15,302
