Best Vacation rentals and Airbnb offers in Anna Maria, FL
9.8 35 reviews
Anna Maria, FL
07/15 – 07/17
$1828/nighttotal: $3656 (2 )
Pool*hot Tub*tiki Bar*pickleball Court*dock
4 5
apartment , Anna Maria
This Anna Maria Island vacation home offers waterfront access, a private pool, and is a 15-minute walk from Bay Boulevard Beach, Historic Green Village, and Bayfront Park, with Palmetto Avenue Beach and the Anna Maria Island Museum also nearby. This 2710-square-foot house features four bedrooms, three bathrooms, accommodates eight guests, and includes a fully equipped kitchen, a private pool, Jacuzzi, tennis court, and access to on-site amenities such as a water park, spa tub, and game room.
9.2 55 reviews
Anna Maria, FL
10/31 – 11/10
$281/nighttotal: $2810 (10 )
Adorable Duplex On Ami! With Pool, Near Bean Point Beach
2 2
apartment , Anna Maria
This Anna Maria Island ground-level duplex is located less than a 10-minute walk from Bean Point Beach and a 10-minute drive from Bayfront Park, offering easy access to Pine Avenue's shops and restaurants. This 790-square-foot, two-bedroom, one-bathroom unit sleeps six guests and features a newly remodeled interior, a fully equipped kitchen, a shared community pool, and a professional linen program.
10 60 reviews
Anna Maria, FL
06/27 – 07/04
$948/nighttotal: $6636 (7 )
Tucked Away In Anna Maria
3 2
apartment , Anna Maria
This Anna Maria Island vacation rental, located in the North End, is a short 0.3-mile walk from the beach and 0.6 miles from the free island trolley. This newly renovated 1,566-square-foot home features three bedrooms, two bathrooms, sleeps six, and boasts a private heated pool, spa, dock, and large screened lanai.
9.5 141 reviews
Anna Maria, FL
08/04 – 08/06
$211/nighttotal: $422 (2 )
"Paradise" By The Private (Heated) Pool Light!
1 2
apartment , Cortez
This Cortez vacation rental, located one mile from the Gulf Coast beaches, offers a secluded tropical escape. The property features a private heated pool, large screened lanai, BBQ grill, outdoor shower, complete kitchenette, queen-sized bed, updated bathroom, Wi-Fi, Smart TV, washer, dryer, and accommodates two guests.
9.1 74 reviews
Anna Maria, FL
08/04 – 08/06
$244/nighttotal: $488 (2 )
2br | Patio | Dog Friendly | Washer/dryer
2 2
apartment , Anna Maria
This dog-friendly suite is located one block from Bimini Bay inlets and a five-minute walk to beach access, putting you within easy walking distance of local shops, dining, and the fishing pier in Anna Maria. This two-bedroom, one-bathroom vacation rental accommodates up to four guests and features a full kitchen with stainless steel appliances, a private lanai, outdoor dining with gas grills, and step-free access.
10 2 reviews
Anna Maria, FL
07/05 – 07/11
$354/nighttotal: $2124 (6 )
Family Fun House: Pool & Mini-golf
1 11
house , Bayshore Gardens
This vacation home in Bradenton's Bayshore Gardens is located 3.1 miles from Sarasota Bradenton International Airport and 4.7 miles from the Sarasota International Convention Center and the John and Mable Ringling Museum of Art. This 1700 square foot house accommodates 16 guests with 5 bedrooms and 2 bathrooms, featuring a full kitchen, outdoor swimming pool, on-site mini-golf, free WiFi, and parking.
9.4 110 reviews
Anna Maria, FL
07/28 – 08/03
$1074/nighttotal: $6444 (6 )
Canalfront Home, Saltwater Pool, Near Beaches And Shopping - Sunrise Shore
5 11
apartment , Anna Maria
This five-bedroom Anna Maria Island vacation rental is located less than a mile from Island Players and Anna Maria Beach, and within a five-minute drive of the Anna Maria Island Museum and Historical Park and Bradenton Beach. This 11-guest home offers a private pool, access to a water park, a fully equipped kitchen, a washing machine, barbecue grills, and a prime location directly on the beach.
9.9 34 reviews
Anna Maria, FL
07/05 – 07/11
$1277/nighttotal: $7662 (6 )
Family Tides - 2 Homes In 1 Steps To Beach W Rooftop Views Heated Pool Close To Bridge St
6 11
house , Bradenton Beach
Family Tides, a spacious Bradenton Beach home, offers direct beach access and proximity to Bridge Street's dining and shopping, located within six miles of Anna Maria City Pier. This 2,290-square-foot vacation rental boasts seven bedrooms, four bathrooms, a private heated pool, a rooftop terrace, and a fully equipped kitchen, accommodating large families or groups.
10 38 reviews
Anna Maria, FL
06/27 – 07/04
$244/nighttotal: $1708 (7 )
Endless Summer- On Pine Ave, Steps To Beach & Pier W/ Water View & Dock
2 2
apartment , Anna Maria
This Anna Maria Island waterfront condo, located on Pine Avenue, offers easy walking access to Anna Maria City Pier, the beach, and numerous restaurants and shops. This 830-square-foot, two-bedroom, one-bathroom apartment sleeps four and features a private dock perfect for kayaking and fishing, a terrace, free parking, and a full kitchen with a dishwasher.
10 66 reviews
Anna Maria, FL
07/24 – 08/01
$1662/nighttotal: $13296 (8 )
2 Min Walk To Gulf~3 King+bunk~pool+spa+golf+bikes
1 7
apartment , Anna Maria
This luxurious Bahamian-style home is located on Anna Maria Island's north end, a two-minute walk from the Gulf beach and a three-minute bike ride from Bean Point and Pine Avenue. This three-bedroom, three-bathroom vacation rental sleeps eight guests and boasts a heated saltwater pool, Jacuzzi, fully equipped kitchen, and numerous amenities including beach gear, bikes, and outdoor games like a three-hole putt-putt course.
9.8 12 reviews
Anna Maria, FL
06/27 – 07/04
$375/nighttotal: $2625 (7 )
102 M² House ∙ 2 Bedrooms ∙ 6 Guests
2 2
house , Anna Maria
This family-friendly house is located in Anna Maria, where guests can enjoy a peaceful vacation surrounded by nature. The house has received excellent user ratings, indicating its high quality and guest satisfaction. The house has two bedrooms and a floor area of 1100 square feet, accommodating up to six guests. It features a fully equipped kitchen, air conditioning, a garden, and parking. Guests can enjoy amenities such as a fridge, freezer, microwave oven, and dishwasher. The house also offers internet access for guests' convenience.
9.4 3 reviews
Anna Maria, FL
07/24 – 08/01
$341/nighttotal: $2728 (8 )
Private Balconies, Walk To Holmes Beach, Sleeps 8, Access To Heated Pool
3 7
apartment , Holmes Beach
This Holmes Beach condo is located adjacent to a mangrove preserve, offering tranquil views and is less than 1 mile from the Gulf beaches, boutique shopping, and local restaurants. This 1330 sq ft condo accommodates up to 8 guests with 3 bedrooms and 3 bathrooms, featuring a heated community pool, private balconies, in-unit laundry, and a full kitchen.
Best Anna Maria, FL vacation rentals with a balcony
10 14 reviews
Anna Maria, FL
07/15 – 07/17
$648/nighttotal: $1296 (2 )
Luxury 2br Oceanfront Condo + Rooftop Patio
2 5
apartment , Holmes Beach
This beachfront Holmes Beach condo is steps from Island Gallery West and Bradenton Beach, and within a mile of Holmes Beach and Manatee Public Beach. The 1190-square-foot unit features two bedrooms, two bathrooms, accommodates six guests, and includes a fully equipped kitchen, private balcony, free WiFi, on-site parking, and beach access with provided sun loungers and towels.
10 22 reviews
Anna Maria, FL
06/27 – 07/04
$1664/nighttotal: $11648 (7 )
Luxury Ami Home With Pool, Rooftop Deck, And Putting Green! 2 Blocks To Beach!
5 5
apartment , Anna Maria
This Anna Maria Island beachfront home, near Bradenton Beach, is a short walk from the Island Players and within one mile of Bean Point and Anna Maria beaches. This 2,600-square-foot vacation rental boasts five bedrooms, four bathrooms, accommodates twelve guests, and features a private pool, hot tub, BBQ grills, and on-site water park.
Anna Maria, FL
07/28 – 08/03
$669/nighttotal: $4014 (6 )
3-minutes To Beach! Whole Duplex, Experience Anna Maria Island Paradise!
4 11
apartment , Bradenton Beach
This beachfront vacation home in Bradenton Beach, Florida, is a five-minute walk from Anna Maria Sound and Bradenton Beach, and within one mile of the Aluna Wellness Center & Spa and Bradenton Beach Marina. This 1,680-square-foot rental boasts six bedrooms, four bathrooms, and sleeps twelve, featuring a fully equipped kitchen, private balcony, free parking, and Wi-Fi.
Anna Maria, FL
07/28 – 08/03
$1059/nighttotal: $6354 (6 )
Recently Renovated With Large Pool On The North End Of Ami
4 11
house , Anna Maria
This Anna Maria Island vacation home is a five-minute walk from the beach and a half-mile from the Anna Maria City Pier, offering easy access to Anna Maria Island's attractions. This 1300-square-foot property features four bedrooms, four bathrooms, and accommodates up to 23 guests, boasting a private pool, fully equipped kitchen, and air conditioning.
Our Favorite Family-Friendly Vacation Rentals in Anna Maria, FL
These family-friendly vacation rentals in Anna Maria, FL offer spacious layouts and easy access to local beaches.
10 3 reviews
Anna Maria, FL
07/05 – 07/11
$708/nighttotal: $4248 (6 )
4br Oasis W/pool & Firepit Near Ami & Img
4 11
apartment , Bradenton
This family-friendly apartment in Bradenton is located minutes from IMG Academy, G.T. Bray Park, Anna Maria Island, SRQ airport, and shopping and dining on Cortez Road and Manatee Avenue. This 1770 sq ft residence accommodates up to 13 guests with 4 bedrooms and 2 bathrooms, featuring a private heated pool, electric vehicle charging station, and complimentary beach gear.
Anna Maria, FL
06/27 – 07/04
$1577/nighttotal: $11039 (7 )
Hibiscus Haven Your Perfect Island Getaway
4 9
apartment , Anna Maria
This Anna Maria condo offers direct water views and is steps from the Gulf beaches, providing convenient access to the free island trolley and proximity to boutiques, cafes, and waterfront restaurants. This 1730 square foot residence features 4 bedrooms, 2 bathrooms, a private heated pool and spa, a modern kitchen, and accommodates up to 10 guests, with pets allowed.
9.7 82 reviews
Anna Maria, FL
06/27 – 07/04
$583/nighttotal: $4081 (7 )
Am I Dreaming: Heated Pool, Family Friendly Home, 3-min Walk To Beach!
3 5
apartment , Holmes Beach
This 3-bedroom, 2-bathroom house is located in Holmes Beach, Florida, within a 15-minute walk of Bradenton Beach and Palmetto Avenue Beach, and within 2 km of Island Players and Anna Maria Island Museum and Historical Park. The 1,220-square-foot house features a private pool, a terrace, a garden, a tennis court, and a fully equipped kitchen, accommodating up to 6 guests.
9.9 132 reviews
Anna Maria, FL
07/28 – 08/03
$549/nighttotal: $3294 (6 )
Stunning!- Game Room, Pool, Beaches & Full Remodel!
4 11
apartment , Bradenton
This Bradenton vacation home, near the Gulf of Mexico and within three miles of Blake Medical Center, Smugglers Cove Adventure Golf, and The Bishop Museum of Science and Nature, offers convenient access to area attractions. This 2200-square-foot property features four bedrooms, two bathrooms, a private pool, and a fully equipped kitchen, comfortably accommodating larger families or groups with amenities including free Wi-Fi and on-site parking.
Frequently Asked Questions about vacation rentals in Anna Maria, FL
What are some interesting places to visit in or near Anna Maria, FL?
Anna Maria Island is full of charm! You've got to check out the historic City Pier in Bradenton Beach, where you can often see dolphins playing. For a taste of local history, visit the Anna Maria Island Museum. And if you're looking for a unique shopping experience, head over to the Pine Avenue shops in Anna Maria.
What are the best Airbnb and vacation rentals in Anna Maria, FL?
Which walking or cycling routes are the best in Anna Maria, FL?
The paved path along the Gulf Drive is a popular choice for walking and biking, offering stunning views of the beach. For a more scenic route, try the Anna Maria Island Nature Trail, where you can spot native wildlife. And if you want to explore the island's history, take a walk down the historic streets of Anna Maria.
What are the most popular Airbnbs in Anna Maria, FL?
What sports or outdoor activites can visitors enjoy in and around Anna Maria, FL?
Anna Maria Island is a paradise for outdoor enthusiasts! You can swim, sunbathe, and surf on the beautiful beaches. Try your hand at paddleboarding or kayaking in the calm waters of the Gulf. And for a more adventurous experience, rent a boat and explore the nearby islands.
What are the best vacation rentals with a pool in Anna Maria, FL?
What other towns or cities can be easily accessed from Anna Maria, FL?
You can easily reach nearby cities like Bradenton, Sarasota, and St. Petersburg from Anna Maria Island. Bradenton is just a short drive away and offers a variety of attractions, including the South Florida Museum and the Bishop Museum of Science and Nature. Sarasota is known for its art scene and beautiful beaches, while St. Petersburg is home to the Dali Museum.
What are the best rentals for families and kids in Anna Maria, FL?
What amenities are commonly available in vacation rentals in Anna Maria, FL?
Most vacation rentals in Anna Maria offer a range of amenities to make your stay comfortable. You can expect to find private pools, hot tubs, fully equipped kitchens, laundry facilities, and even private balconies or patios. Many rentals also offer access to beach chairs, umbrellas, and other beach essentials.
What are the best rentals or Airbnbs with a jacuzzi in Anna Maria, FL?
What time of year is best to rent a vacation rental Anna Maria, FL?
The best time to visit Anna Maria Island really depends on your preferences. If you're looking for warm weather and sunshine, the peak season runs from December to April. For a more relaxed and budget-friendly experience, consider visiting during the shoulder seasons, from May to June or September to November.
Destinations nearby
Best Anna Maria, FL vacation rentals with parking
9.4 71 reviews
Anna Maria, FL
06/21 – 06/26
$281/nighttotal: $1405 (5 )
1 Mi To Anna Maria Island: Pet-friendly Retreat
2 3
house , Cortez
This charming house is located in Cortez, Florida, just a short walk from Bradenton Beach and Cortez Beach, offering easy access to the beautiful Gulf Coast waters. The property has received excellent ratings for cleanliness, location, and overall user experience. This 2-bedroom, 1-bathroom home comfortably accommodates up to 4 guests and spans 1190 square feet. The house comes equipped with a full kitchen, a relaxing patio, and a spa, perfect for enjoying the Florida sunshine and creating lasting memories.
9.8 44 reviews
Anna Maria, FL
07/15 – 07/17
$947/nighttotal: $1894 (2 )
Anna Maria Beach Cottage 110 Traditional Beach Cottage, Moments From The Sand!
3 5
apartment , Anna Maria
This Anna Maria Island vacation rental is just a short walk from Bradenton Beach and Palmetto Avenue Beach, making it easy to enjoy the island's beautiful shores. Guests rave about the excellent location and the comfortable accommodations. The three-bedroom home is perfect for families or groups of up to seven people, offering 1130 square feet of space. Enjoy amenities like a private pool, a spa, a fully equipped kitchen, and a terrace with barbecue grills.
9.6 33 reviews
Anna Maria, FL
06/27 – 07/04
$511/nighttotal: $3577 (7 )
Anna Maria Island Home With Private Pool! - Peach Bellini
2 5
apartment , Holmes Beach
This two-bedroom, two-bathroom vacation home in Holmes Beach provides direct beach access and is within walking distance of Bradenton Beach and Island Gallery West. The 980-square-foot home features a private pool, a fully equipped kitchen, and a sofa bed, accommodating up to six guests.
9.0 4 reviews
Anna Maria, FL
06/27 – 07/04
$940/nighttotal: $6580 (7 )
Twin Tides, 2 Kitchens! Pool, Spa, Golf Cart, Putting Green, Tiki Bar, Sleeps 14
4 9
apartment , Holmes Beach
This pet-friendly vacation home in Holmes Beach is located just a 5-minute walk to Bradenton Beach and a 14-minute walk to Island Gallery West. This spacious 4-bedroom, 5-bathroom condo accommodates up to 12 guests and features a private swimming pool, covered parking, a well-equipped kitchen with an oven and stovetop, and on-site activities like kayaking and bicycle rentals.
Neighborhoods and points of interest in Anna Maria, FL
Browse Vacation Rentals with a Pool in Anna Maria, FL
Complement your beach days with a dip in the pool at these premier vacation rentals in Anna Maria, FL.
9.4 1138 reviews
Anna Maria, FL
08/04 – 08/06
$265/nighttotal: $530 (2 )
Tortuga Inn Beach Resort
1 2
resort , Bradenton Beach
Tortuga Inn Beach Resort is located in Bradenton Beach, Florida, just steps away from the beach, marina, and wellness center. The resort has received excellent ratings for its location, cleanliness, and overall experience. The resort offers comfortable accommodations with direct beach access and two outdoor pools. Guests can enjoy a relaxing atmosphere, room service, and a variety of amenities including a garden, a terrace, a jacuzzi, and parking.
9.3 37 reviews
Anna Maria, FL
08/15 – 08/17
$431/nighttotal: $862 (2 )
Quiet Beach Cottage. Shared Community Pool And Grill. Close To Beach!
2 4
apartment , Anna Maria
This Anna Maria vacation rental is conveniently located just a short walk from Bradenton Beach, Bayfront Park, and Anna Maria Beach, with Bean Point Beach and Anna Maria City Pier within a 15-minute reach. The apartment has received excellent user and location ratings, as well as a very good cleanliness rating. This two-bedroom, one-bathroom apartment offers a comfortable and convenient space for your stay. The apartment features a fully equipped kitchen, a private patio, a washing machine, and a barbecue grill, allowing you to enjoy the best of Anna Maria.
9.8 8 reviews
Anna Maria, FL
06/21 – 06/26
$263/nighttotal: $1315 (5 )
Paradise Awaits By Coastal Chic Vacations
2 3
apartment , Bradenton
This Anna Maria Island condo, a two-minute drive from Manatee Beach and four minutes from other Bradenton beaches, offers convenient access to Anna Maria Island's attractions. This 1,500-square-foot, two-bedroom, two-bathroom unit features an open-concept living area, screened lanai, fully equipped kitchen, in-unit laundry, assigned parking, and sleeps five with a queen sleeper sofa; resort-style amenities include a heated pool, splash pad, playground, grilling area, and private beach club access.
9.8 12 reviews
Anna Maria, FL
08/04 – 08/06
$1547/nighttotal: $3094 (2 )
Knot 4 Reel: Gorgeous Canal Front W/pool, Hot Tub, Dock And Steps To The Bay!
4 2
apartment , Anna Maria
This Anna Maria Island vacation home boasts a waterfront location less than a mile from Bay Boulevard Beach and Anna Maria Beach, and within five minutes of Historic Green Village and the Anna Maria City Pier. This 2,220-square-foot house features four bedrooms, three bathrooms, sleeps eight guests, and includes a private pool, fenced yard, free WiFi, and a fully equipped kitchen with a refrigerator, microwave, and dishwasher; on-site amenities include a water park and barbecue grills.
Top-Rated Oceanfront Vacation Rentals in Anna Maria, FL
Discover charming seaside vacation rentals in Anna Maria, FL near the coast. Browse our favorite coastal picks to find your perfect beach-town match.
9.0 169 reviews
Anna Maria, FL
09/10 – 09/13
$421/nighttotal: $1263 (3 )
Sea's The Day
2 4
house , Anna Maria
9.7 69 reviews
Anna Maria, FL
07/28 – 08/03
$502/nighttotal: $3012 (6 )
<1 Mile Walk 2 Beach! 1 Lvl, 2 King, Heated Pool
1 11
apartment , West Bradenton
9.5 232 reviews
Anna Maria, FL
08/04 – 08/06
$760/nighttotal: $1520 (2 )
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
3 2
apartment , Anna Maria
9.6 4 reviews
Anna Maria, FL
07/03 – 07/06
$2057/nighttotal: $6171 (3 )
Luxury North End Escape | 3 King Beds + Pool/spa
3 3
apartment , Anna Maria
Top-Rated 5-Star Vacation Rentals in Anna Maria, FL
Refined interiors and prime locations make these luxury waterfront vacation rentals in Anna Maria, FL the ideal choice for your stay.
Anna Maria, FL
07/05 – 07/11
$620/nighttotal: $3720 (6 )
Manatee Haven Pool Games Hot Tub Firepit
4 11
house , West Bradenton
Best Vacation Rentals with a Steam Room in Anna Maria, FL
Maximize your recovery with an on-site sauna, a standard feature at these premier Anna Maria, FL vacation rentals.
Anna Maria, FL
06/27 – 07/04
$279/nighttotal: $1953 (7 )
Dans Florida Condos Sea Cove At Runaway Bay
2 2
house , Bradenton Beach
10 11 reviews
Anna Maria, FL
07/03 – 07/06
$270/nighttotal: $810 (3 )
Luxury Bayview Wellness Retreat W/pool, Salt-water Jacuzzi, Hot Tub...+ More!
2 3
apartment , Bayshore Gardens
9.6 19 reviews
Anna Maria, FL
06/27 – 07/04
$387/nighttotal: $2709 (7 )
Runaway Bay 262 - Beach, Bay, Pool And Gym Special Rates August - October
2 2
apartment , Bradenton Beach
Anna Maria, FL
10/31 – 11/10
$1312/nighttotal: $13120 (10 )
Luxury Waterfront - Sauna - Games - Minigolf - Gym
