50 Best Anna Maria Island Vacation rentals on Holiday Lettings - Beach rentals

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Anna Maria Island

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1,652 Vacation rentals

(37) Excellent 

41

Townhouse rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Our modern, luxury townhouse within the Bermuda Bay Club condominium enjoys a fantastic location right at the beach on Bradenton Beach; within easy walking to a number of shops, restaurants and a host of activities. Packed with all the mod cons (including free WiFi, tel …see more

from $172 / night

$1,200 - $1,900 / week

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from $172 / night

(1) Excellent 

8

Anna Maria Island Vacation apartment rental

Florida / Anna Maria Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our apartment is located in close proximity to one of the most beautiful beaches of Florida. The apartment has a master bedroom with king size bed, TV, bathroom with shower or shower basin and toilet and a sep. Guest room with adjoining bath towels and linens are provid …see more

from $112 / night

$784 - $995 / week

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from $112 / night

11

Vacation condo in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 60 nights min

  • 2 bedrooms
  • Sleeps 6
  • 60 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This beautiful island condo is newly refurbished and redecorated for a perfect get-away. This quiet, 55+ community is a paradise. Situated in Anna Maria Island, Florida, the island has quiet, old-Florida charm with numerous restaurants, shops, and conveniences. A fre …see more

from $94 / night

$654 / week

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from $94 / night

16

Vacation townhouse in Bradenton Beach

Anna Maria Island / Bradenton Beach

3 6 90 nights min

  • 3 bedrooms
  • Sleeps 6
  • 90 nights min
  • Child friendly
At the entrance to Anna Maria Island, on Perico Island overlooking Anna Maria Sound is the gorgeous 220-acre island oasis and Florida’s newest private waterfront resort. Within this gated community is our fully furnished southern coastal coach home, which features 3 be …see more

from $250 / night

$1,750 / week

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avg. 2 hours 20 minutes

from $250 / night

(6) Excellent 

22

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps …see more

from $165 / night

$885 - $1,390 / week

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avg. 2 hours 36 minutes

from $165 / night

42

Cottage rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

4 15 Min stay varies

  • 4 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
We have some openings available April 8-15! Our family has lovingly restored this HISTORIC 1939 FISHING CAMP located on beautiful Sarasota Bay. You'll be surrounded by water living on the narrowest point of Anna Maria Island. Sugar sand BEACH only a 1 minute stroll a …see more

from $115 / night

$800 - $1,500 / week

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from $115 / night

(1) Excellent 

12

Vacation apartment in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Updated 2 bedroom townhouse condo in Bradenton Beach with an unobstructed view of the Gulf of Mexico. Grab your beach chairs, umbrella, cooler and towels (provided) cross Gulf Drive and you're on the beach in a minute. If your enjoy fishing, the pier extending out into …see more

from $130 / night

$900 - $1,000 / week

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from $130 / night

(2) Very Good 

35

Vacation villa in Anna Maria

Anna Maria Island / Anna Maria

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
Anna Maria Island, This property is located directly across from the famous Manatee County Public Beach. Groomed daily, Lifeguards, restaurants, surf shop and more.. Free trolley stops there both northbound and south every 20 minutes. The location is also right in the h …see more

from $150 / night

$895 - $1,600 / week

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from $150 / night

(8) Excellent 

26

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This well-furnished two bedroom condo is next to a quiet nature preserve and has a fine view of the bay separating Anna Maria Island from Florida's mainland as well as the Sandy Pointe heated swimming pool. The beach is just 3 small blocks away with its bright white san …see more

from $125 / night

$720 - $1,050 / week

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from $125 / night

(23) Very Good 

17

Vacation home rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Aloha and welcome to our Island Home. Ohana is Hawaiian for family and that is who you are when you stay with us. Our retreat is nestled on Anna Maria Island, Florida and is a short 5 minute walk to the white sand beaches and turquoise waters of the Gulf of Mexico. We …see more

from $135 / night

$850 - $1,300 / week

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avg. 3 hours 27 minutes

from $135 / night

(1) Excellent 

14

Vacation condo in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Relax in the casual comfort of an island paradise, and have a true Old Florida experience on Anna Maria Island, where riding bikes is the preferred way to travel and indulging in the simple pleasures of life - sun, beach, scuba dive, Snorkel and relaxation are th …see more

from $150 / night

$850 - $1,000 / week

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from $150 / night

25

Bradenton Beach Vacation cottage rental

Anna Maria Island / Bradenton Beach

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 0 mi
  • Child friendly
  • Car not necessary
This STAND ALONE, VERY CHARMING, cottage is in a very peaceful setting with huge brick courtyard. This is not like most other vacation rentals that require you to climb 1-2 stories. This is a stand alone ground level home! We have just invested in a new kitchen, bathro …see more

from $199 / night

$995 - $1,999 / week

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avg. 3 hours 54 minutes

from $199 / night

11

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Swimming pool
Very spacious two bedroom Condo with a large living room. Flat Screen TV, fully equipped kitchen with all the appliances. Not far from the beach, and short distance to area shopping. Unit has heated pool, and a relaxing Pool deck area. Main bedroom has a King size bed w …see more

from $145 / night

$795 - $1,200 / week

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from $145 / night

(3) Very Good 

15

Vacation home rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Perhaps Shady Palms will become "your place on the beach." Walk into a charming, Old Florida style beach cottage with a view of the beautiful Gulf of Mexico from every room in the house. Continue through the back door, and into the yard and you are one step from the wi …see more

from $329 / night

$2,300 - $2,600 / week

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from $329 / night

16

Vacation townhouse in Bradenton Beach

Anna Maria Island / Bradenton Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Key West Style Townhouse with a beautiful Gulf, Beach view in Anna Maria Island. This large townhouse with 3 bedrooms, 3 1/2 baths multi level front unit is the ideal location for family. Overlooking Gulf Drive North located on the West Coast of Florida, Anna Maria Isl …see more

from $269 / night

$1,799 / week

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from $269 / night

19

Apartment rental in Anna Maria Island with shared pool

Florida / Anna Maria Island

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children
Pelican Cove 5 - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 5 people. Florida's Finest Beach to Bay Resort with a Community pool! Beautiful White Sand Beaches and Crystal Blue Waters Wait Your Arrival!~ Located near the shops and restaurants on Bridge …see more

from $200 / night

$1,200 - $1,900 / week

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from $200 / night

(5) Very Good 

21

Apartment rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Aloha and welcome to our Island Home. “Ohana” is Hawaiian for family and that is who you are when you stay with us. Our retreat is nestled in Anna Maria Island, Florida. Ohana Hale Beachside is 150 feet to the white sand beaches and turquoise waters of the Gulf of Mex …see more

from $125 / night

$800 - $1,150 / week

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Responds fast!
avg. 3 hours 27 minutes

from $125 / night

29

Bradenton Beach Vacation studio rental

Anna Maria Island / Bradenton Beach

Studio 4 1 night min

  • Studio
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask about children
Club Bamboo South unit 224, Gulf Front Studio, ocean view, maximum occupancy of 4 people. Community pool, community BBQ grill. Beautiful Gulf Front Studio directly on the Gulf of Mexico! Open the sliding glass doors to the covered private balcony and listen to the soun …see more

from $167 / night

$1,168 - $1,754 / week

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from $167 / night

(4) Excellent 

23

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning
Two bedroom two bath condo located upstairs in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room …see more

from $200 / night

$1,090 - $1,750 / week

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Responds fast!
avg. 2 hours 36 minutes

from $200 / night

30

Holmes Beach Vacation condo rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Tastefully decorated, two-bedroom, two-bath condo, located in Holmes Beach on quaint Anna Maria Island on the Gulf of Mexico. The condo complex has 32 units on one of Florida's finest beaches. You can walk the beach for miles in both a northerly and southerly direction. …see more

from $172 / night

$1,200 / week

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from $172 / night

(3) Excellent 

69

Vacation apartment in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you are at the beach. The Anna Maria Island Beach Palms 5B is completely surrounded by water and has …see more

from $150 / night

$1,050 / week

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Responds fast!
avg. 2 hours 34 minutes

from $150 / night

(14) Excellent 

33

Bradenton Beach Vacation apartment rental

Anna Maria Island / Bradenton Beach

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
2br/1ba elevated turnkey steps from the bay, 2 blocks from the Gulf of Mexico. Fully furnished. Children's Park and kayak launch at end of street. Beach chairs, towels, grill provided. Gorgeous view of bay from front porch swing. Perfect place for relaxing family vacati …see more

from $110 / night

$750 - $1,100 / week

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from $110 / night

11

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
3011 Ave E-2 Triplex Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. VRC16-000051 Wouldn't you rather be at the Beach?~ Nestled in a quiet residential area just one half block from the beach, is a tri-plex offering a pleasant environment for individual guests …see more

from $145 / night

$1,000 - $1,595 / week

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from $145 / night

10

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Sandy Beach Access Duplex, 2 bedrooms, 2 baths, 6 Places Newly renovated, fully furnished, 2 BR 2 Bath duplex. 202B 76th Street, Holmes Beach, FL 34217 New landscaping. 1 1/2 blocks (300 yards) to a beautiful sandy beach. Cable TV's, Wireless Internet, DVD Player. Lau …see more

from $108 / night

$750 - $900 / week

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Responds fast!
avg. 2 hours 49 minutes

from $108 / night

23

Vacation villa rental

Anna Maria Island / Holmes Beach

1 8 Min stay varies

  • 1 bedroom
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning
Two bedroom two bath condo located upstairs in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room …see more

from $200 / night

$1,090 - $1,750 / week

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Responds fast!
avg. 2 hours 36 minutes

from $200 / night

(10) Excellent 

25

Vacation home in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
An elegant beach-house that redefines the idea of island comfort, built with love and an extreme attention to detail. Every room of the house has a unique ambiance combining color, textures and accent lighting. The outdoor area is one of the most spacious on the island …see more

from $259 / night

$1,813 / week

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Responds fast!
avg. 1 hour 27 minutes

from $259 / night

(1) Excellent 

17

Home rental in Anna Maria

Anna Maria Island / Anna Maria

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
As an artist this private three bedroom and two bath multi-level elevated vacation home has been our family retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll …see more

from $210 / night

$1,400 - $1,700 / week

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from $210 / night

(1) Excellent 

18

Vacation apartment rental

Anna Maria Island / Holmes Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
7901 Palm Dr- Duplex-2 bedroom 1 bath-, maximum occupancy of 4 people. VRC16-000060 This is a very cute and well- appointed 2 bedroom 1 bath duplex. It has a Queen size bed in the master bedroom and a 2 twin size beds in the guest bedroom. It has a very nice comforta …see more

from $143 / night

$1,000 - $1,540 / week

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from $143 / night

(1) Very Good 

15

Bradenton Beach Vacation apartment rental

Anna Maria Island / Bradenton Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Relax in the casual comfort of an island paradise, and have a true Old Florida experience on Anna Maria Island, where riding bikes is the preferred way to travel and indulging in the simple pleasures of life - sun, beach, scuba dive, Snorkel and relaxation are the favo …see more

from $150 / night

$1,000 / week

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from $150 / night

(5) Excellent 

Certificate of Excellence

21

Holmes Beach Vacation condo rental

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Very contemporary condo (danish style), just refurnished and remodeled, and equipped with more than everything you need for a relaxing and unforgettable vacation in Paradise. The unit is inspiring and gives you a laid back feeling immediately after entering. A huge poo …see more

Certificate of Excellence

from $100 / night

$650 - $1,400 / week

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from $100 / night

(3) Excellent 

19

Vacation apartment rental

Anna Maria Island / Holmes Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Lovely Bayside Condo recently remodeled, 2 Bedroom, 2 Bathroom, fully air conditioned, screened lanai, heated pool and covered parking. Easy access to: retail shops, grocery store and restaurants. 200 hundred yards to Free Island Trolley. Five minute walk to white sand …see more

from $128 / night

$895 / week

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from $128 / night

12

Bradenton Beach Vacation studio rental

Anna Maria Island / Bradenton Beach

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
This beachfront vacation rental is perfectly suited for a family of 4 or a couple looking for a weekend getaway. The rental is in Bradenton Beach and equipped with 1 California King and 2 twin sleepers. The balcony features a fantastic view of the Gulf of Mexico where y …see more

from $125 / night

$800 - $1,680 / week

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Responds fast!
avg. 2 hours 17 minutes

from $125 / night

(10) Excellent 

21

Vacation apartment in Bradenton Beach

Anna Maria Island / Bradenton Beach

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Anna Maria Island boasts one of the longest stretches of sugar white beaches in Florida, and clear, aqua-marine water. Enjoy the natural setting from this spectacular townhouse on Bradenton Beach. This three bedroom, two-and-a-half bath home offers direct Gulf views, …see more

from $250 / night

$1,400 - $1,500 / week

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from $250 / night

(4) Excellent 

49

Holmes Beach Vacation home rental

Anna Maria Island / Holmes Beach

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Beautiful 5 bedroom 4 bathroom vacation home in Holmes Beach, just steps from the beach with fantastic Gulf views. This home is the perfect beach getaway with everything you could want while enjoying Anna Maria Island. Just imagine waking up to the sound of the surf r …see more

from $495 / night

$3,000 - $7,550 / week

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avg. 2 hours 17 minutes

from $495 / night

(1) Very Good 

11

Vacation apartment rental

Anna Maria Island / Holmes Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Swimming pool
Gorgeous Efficiency and steps to white sandy beaches from this 1 bedroom, 1 bath elevated vacation rental, one story up overlooking pool area. Stairs go up to small deck in front of the efficiency. With 3 x 8 open deck to enjoy the sunsets, or overlooking pool. Feel th …see more

from $125 / night

$700 / week

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from $125 / night

(1) Very Good 

25

Vacation condo rental

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
GULF FRONT CONDO - Direct gulf front 2 bedroom 2 bath upstairs condo with a breathtaking view of the Gulf of Mexico. Large private screened balcony overlooking the beach. Fully equipped kitchen. Owner has provided many extras for your enjoyment. Heated pool and assigned …see more

from $169 / night

$850 - $1,575 / week

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Responds fast!
avg. 2 hours 18 minutes

from $169 / night

(2) Excellent 

32

Anna Maria Vacation condo rental

Anna Maria Island / Anna Maria

2 4 13 nights min

  • 2 bedrooms
  • Sleeps 4
  • 13 nights min
  • Child friendly
3 Miles of white sandy beaches..Beautiful beach front condo. Location is amazing for the perfect vacation bedrooms are a split design for privacy the panoramic views from the condo are breathtaking listen to the waves day and night and enjoy the beautiful SUNSETS per …see more

from $179 / night

$1,250 / week

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from $179 / night

4

Vacation condo rental

Anna Maria Island / Holmes Beach

1 2 6 nights min

  • 1 bedroom
  • Sleeps 2
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Dates Available: Check in May 5, 2018, Check out May 11, 2018. One bedroom at Resort 66 on beautiful Anna Maria Island. Check out the pictures on Trip Advisor and you will be surprised. Resort is located on the beach with pool view. Just a few steps to the beach. Many u …see more

from $150 / night

$1,050 / week

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from $150 / night

18

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up …see more

from $200 / night

$1,090 - $1,695 / week

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Responds fast!
avg. 2 hours 8 minutes

from $200 / night

20

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps …see more

from $200 / night

$1,200 - $1,850 / week

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Responds fast!
avg. 2 hours 8 minutes

from $200 / night