The 10 best holiday rentals in Anna Maria, USA | Booking.com
Skip to main content

Holiday Rentals in Anna Maria

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Anna Maria

The best holiday rentals in Anna Maria

Check out our pick of great holiday rentals in Anna Maria

Show hotels on map

Filter by:

Review score

Seabreeze at Anna Maria Island Inn

Bradenton Beach (Near Anna Maria)

Set in Bradenton Beach, within a few steps of Bradenton Beach and 23 km of Sarasota International Convention Center, Seabreeze at Anna Maria Island Inn offers accommodation with an outdoor swimming...

C
CHRISTINE
From
United States
The staff was beyond friendly and accommodating. Very warm greeting and made our stay even better.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 100 reviews
Price from
US$500.32
1 night, 2 adults
Check availability

Steps from the Gulf of Mexico

Holmes Beach (Near Anna Maria)

Located 28 km from John And Mable Ringling Museum Of Art, 28 km from The John And Mable Ringling Museum Of Art and 3 km from Anna Maria City Pier, Steps from the Gulf of Mexico features accommodation...

W
Wladimir
From
Germany
The house, the location, everything
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 28 reviews
Price from
US$270
1 night, 2 adults
Check availability

Captain’s Quarters at Anna Maria Island Inn

Bradenton Beach (Near Anna Maria)

Set within less than 1 km of Cortez Beach and 23 km of The John And Mable Ringling Museum Of Art, Captain’s Quarters at Anna Maria Island Inn offers rooms with air conditioning and a private bathroom...

F
Fonda
From
United States
Walking distance to beach, shopping and some restaurants.
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 118 reviews
Price from
US$223.02
1 night, 2 adults
Check availability

Cottage in Arbor Terrace Resort

Bradenton (Near Anna Maria)

Located in Bradenton, 8.7 km from John And Mable Ringling Museum Of Art and 8.7 km from The John And Mable Ringling Museum Of Art, Cottage in Arbor Terrace Resort offers air conditioning.

G
Gianfranco
From
Italy
The property was really nice, comfortable and clean.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 40 reviews
Price from
US$89.04
1 night, 2 adults
Check availability

Vera’s vacation

Bradenton (Near Anna Maria)

Vera’s vacation is a recently renovated holiday home in Bradenton, where guests can makes the most of its outdoor swimming pool, garden and barbecue facilities. A hot tub is available for guests.

b
bonnie
From
United States
Location was great. House and yard were nice. Host was available if there were any questions. Televisions in every bedroom were a bonus. Use of washer and dryer was a plus.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 35 reviews
Price from
US$266.48
1 night, 2 adults
Check availability

Park Shore Suites St Pete Beach

St Pete Beach (Near Anna Maria)

Set within 600 metres of St. Pete Beach and 6.6 km of John's Pass, Park Shore Suites St Pete Beach offers rooms with air conditioning and a private bathroom in St Pete Beach.

L
Leah
From
Australia
The property has everything you need, fully equipped apartment and the property itself is done so nicely with a bbq and pool. The pool is clean and not overdone with chlorine like many. The host was so helpful and responsive to all our requests.
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 173 reviews
Price from
US$186.15
1 night, 2 adults
Check availability

Waterfront, Pool, Tiki Bar & Grill, Gym, location!

Sarasota (Near Anna Maria)

Featuring air-conditioned accommodation with a private pool, Waterfront, Pool, Tiki Bar & Grill, Gym, location! is set in Sarasota.

s
shirley
From
United States
Enjoyed the entertainment at the bar,staff was great,Pool was busy,so I didn't partcipitate location was good ,liked the marina
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 12 reviews
Price from
US$217.35
1 night, 2 adults
Check availability

Sarasota Cay Club #612 - Heated Pool, Bunk Beds, Huge TV, Tiki Bar, More!

Sarasota (Near Anna Maria)

Set in Sarasota, Sarasota Cay Club #612 - Heated Pool, Bunk Beds, Huge TV, Tiki Bar, More! offers accommodation with a pool with a view and city views.

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 24 reviews
Price from
US$182.85
1 night, 2 adults
Check availability

Waterfront Room, Heated Pool, Tiki Bar & Grill

Sarasota (Near Anna Maria)

Situated in Sarasota, Waterfront Room, Heated Pool, Tiki Bar & Grill provides a pool with a view. Both free WiFi and parking on-site are available at the aparthotel free of charge.

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 7 reviews
Price from
US$217.35
1 night, 2 adults
Check availability

All-New, Private, Huge TV, Heated Pool, Tiki Bar

Sarasota (Near Anna Maria)

Situated 4 km from Sarasota International Convention Center, All-New, Private, Huge TV, Heated Pool, Tiki Bar features accommodation with free WiFi and free private parking.

Scored out of 10, guest rating 6.4
Pleasant - What previous guests thought, 19 reviews
Price from
US$182.85
1 night, 2 adults
Check availability
All holiday rentals in Anna Maria

Most booked holiday rentals in Anna Maria and surroundings in the past month

See all

Highly rated holiday rentals in Anna Maria and nearby

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 59 reviews

    Boasting a patio with garden views, an outdoor swimming pool and a garden, An Island Getaway at Palm Tree Villas can be found in Holmes Beach, close to Anna Maria Island and 29 km from The John And...

    From US$374.37 per night
  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 132 reviews

    Situated in Holmes Beach, a few steps from Holmes Beach, Alamanda Villas on Holmes Beach features accommodation with an outdoor swimming pool, free private parking, a terrace and barbecue facilities.

    From US$526.88 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 100 reviews

    Set in Bradenton Beach, within a few steps of Bradenton Beach and 23 km of Sarasota International Convention Center, Seabreeze at Anna Maria Island Inn offers accommodation with an outdoor swimming...

    From US$398.17 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 8 reviews

    Situated in Bradenton Beach and only 500 metres from Cortez Beach, Tides Inn on the Bay Vacation Homes features accommodation with sea views, free WiFi and free private parking.

    From US$416.50 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 118 reviews

    Set within less than 1 km of Cortez Beach and 23 km of The John And Mable Ringling Museum Of Art, Captain’s Quarters at Anna Maria Island Inn offers rooms with air conditioning and a private bathroom...

    From US$338.96 per night
  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 14 reviews

    Offering a garden and quiet street view, Steps from the Gulf of Mexico II is set in Holmes Beach, 100 metres from Anna Maria Island and 29 km from The John And Mable Ringling Museum Of Art.

  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 28 reviews

    Located 28 km from John And Mable Ringling Museum Of Art, 28 km from The John And Mable Ringling Museum Of Art and 3 km from Anna Maria City Pier, Steps from the Gulf of Mexico features accommodation...

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 8 reviews

    Featuring air-conditioned accommodation with a private pool, pool view and a patio, Sunset Connection - Gulf Place is located in Holmes Beach.

These holiday rentals in Anna Maria and nearby have options with free cancellation

  • Vitamin Sea

    Holmes Beach
    Free cancellation options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Set in Holmes Beach, a few steps from Holmes Beach and 27 km from The John And Mable Ringling Museum Of Art, Vitamin Sea offers air conditioning.

    From US$584.35 per night

  • High Tide

    Holmes Beach
    Free cancellation options available

    Situated in Holmes Beach, a few steps from Holmes Beach and 27 km from The John And Mable Ringling Museum Of Art, High Tide features air-conditioned accommodation with a balcony and free WiFi.

  • Shady Mango home

    Anna Maria
    Free cancellation options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Set in Anna Maria in the Florida region with Anna Maria Island nearby, Shady Mango home offers accommodation with free private parking.

  • Boasting air-conditioned accommodation with a heated pool, sea view and a balcony, Luxury Waterfront Home With A Heated Pool And Spa! is located in Anna Maria.

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 4 reviews

    Featuring air-conditioned accommodation with a private pool, The Cottage on Pine - Luxury Boho Beach Cottage wPvt Heated Pool On Pine Ave is located in Anna Maria.

  • The Palm Leaf home

    Anna Maria
    Free cancellation options available
    Scored out of 10, guest rating 6.0
    Pleasant - What previous guests thought, 1 review

    Set in Anna Maria, less than 1 km from Anna Maria Island and 31 km from Sarasota International Convention Center, The Palm Leaf home offers air conditioning.

  • Island Gem B home

    Anna Maria
    Free cancellation options available

    Set in Anna Maria in the Florida region with Anna Maria Island nearby, Island Gem B home offers accommodation with free private parking.

  • Island Gem A home

    Anna Maria
    Free cancellation options available
    Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Situated in Anna Maria in the Florida region with Anna Maria Island nearby, Island Gem A home features accommodation with free private parking.

Holiday Rentals with swimming pools in Anna Maria and nearby

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 3 reviews

    Boasting air-conditioned accommodation with a balcony, Decked Out - Stunning Home Huge Sunny Resort Style Heated Pool Walk to Pine Ave Beach is set in Anna Maria.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    Situated in Anna Maria, Casa Amiga by Beach Retreats features accommodation with a private pool, a balcony and sea views.

  • Set in Anna Maria, Casa Amiga managed by Beach Retreats offers accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Located in Anna Maria, Vitamin Sea managed by Beach Retreats provides accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Boasting air-conditioned accommodation with a private pool, Coconut Lagoon - Lovely Historic Renovated Cottage wHuge Heated Pool Backyard OasisCabanaBar is set in Anna Maria. 32 km from The John And...

  • Bird of Paradise home is located in Anna Maria, 31 km from Sarasota International Convention Center, 31 km from John And Mable Ringling Museum Of Art, and 31 km from The John And Mable Ringling Museum...

  • Set in Anna Maria, 1.1 km from Anna Maria Island and 31 km from Sarasota International Convention Center, Canario Cottage Home offers air conditioning.

  • Scored out of 10, guest rating 7.2
    Good - What previous guests thought, 7 reviews

    Boasting air-conditioned accommodation with a balcony, Spring Oasis is situated in Anna Maria. Guests can benefit from a patio and an outdoor pool.

Enjoy breakfast in Anna Maria and nearby

  • Situated in Anna Maria in the Florida region with Anna Maria Island nearby, Coconut Bayou home features accommodation with free private parking.

  • Set in Anna Maria in the Florida region with Anna Maria Island nearby, Beach N Bay 204 villa offers accommodation with free private parking.

  • Located in Anna Maria in the Florida region with Anna Maria Island nearby, Beach N Bay home provides accommodation with free private parking.

  • Featuring air-conditioned accommodation with a private pool, Beach A La Mode - 211 is located in Anna Maria. This property offers access to a balcony, free private parking and free WiFi.

  • Situated in Anna Maria, 1 km from Anna Maria Island and 31 km from Sarasota International Convention Center, Our Great Escape home offers air conditioning.

  • Situated in Anna Maria in the Florida region with Anna Maria Island nearby, Manatee Manor Home features accommodation with free private parking.

  • Scored out of 10, guest rating 4.5
    Disappointing - What previous guests thought, 2 reviews

    Boasting air-conditioned accommodation with a private pool, garden view and a balcony, Southern Magnolia is situated in Anna Maria. Guests staying at this holiday home have access to a patio.

  • Set in Anna Maria in the Florida region with Anna Maria Island nearby, Gladiolus On The Water Home offers accommodation with free private parking.

FAQ about holiday rentals in Anna Maria

Research, refine and make plans for your whole trip

Holiday Rentals in New York

Take a look at holiday rentals in New York and explore more of the United States.

Holiday Rentals in Las Vegas

Discover another destination in the United States.

Hotels near Lido Beach

Hotels close to a popular local landmark.

Hotels near Johns Pass and Village Boardwalk

Hotels close to a popular local landmark.

When to visit the United States

Events, prices, the weather and more.

Holiday Rentals in the United States

Pack a bigger bag and see more of the country.

Holiday Rentals in Orlando

Want to extend your trip or still just browsing? Try Orlando, also popular with our guests!

Holiday Rentals in Bradenton

Find more hotels in a city close to Bradenton.

Holiday Rentals in St Pete Beach

Find more hotels in a city close to St Pete Beach.