Showing

PreviousNext property

$278

4 BR / 8 BA / Sleeps 10

2 Reviews

$278

Inquire

Casa Del Sol - 310 Clark Lane

4 BR / 8 BA / Sleeps 10 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Enjoy the Florida vacation life-style at this beautiful custom vacation rental home. From the moment you walk through the front door into the welcoming foyer, you will be happy you chose Casa Del Sol. This home will make your vacation so enjoyable. Just minutes the world famous white sands of Anna Maria Island …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(2)

Beyond expectations

Left on Mar 13, 2011 for a stay in February 2011

Extremely clean rental. Well furnished and had all the amenities needed for vacationing with a family. Short walk to the beach (5 min). Great location for local exploring or traveling off the island. Would definitely rent this property again!

PreviousNext property

$114

2 BR / 2 BA / Sleeps 6

A Hidden Gem: 2BR Family-Friendly Condo with Pool - Holmes Beach vacation rentals
1 / 24

$114

Inquire

A Hidden Gem: 2BR Family-Friendly Condo with Pool

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Note: This property requires a 28-day minimum stay. This two-bedroom, two-bath vacation rental is the perfect size for a romantic getaway, small families or close friends. Located in the Westbay Point & Moorings condominium complex in Holmes Beach, this hidden gem is tucked away from traffic, offering tranquility, …
  • Waterfront
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Porch
  • Suitable for children

PreviousNext property

$264

3 BR / 7 BA / Sleeps 6

2 Reviews

$264

Inquire

La Casa O'Bar

3 BR / 7 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Luxury is within reach at this new direct gulf front two or three bedroom plus library/den luxury holiday condo. Located at 7308 Gulf Dr, Holmes Beach, Anna Maria Island, FL. Relax your cares away in the master suite fit for royalty with king size bed, dual headed shower and Jacuzzi tub. Custom gourmet kitchen …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(2)

Home on the beach

Left on Sep 24, 2008 for a stay in August 2008

We have rented property on a beach for the past 5 years and this property was the best yet. The location was great and we enjoyed the open space. We want to stay in the same building next year. However, we would like to stay on the third floor instead of the second floor.

We really like having a garage to secure our vehicle. This property was like being at home on the beach.

I recommend this …

PreviousNext property

$172

3 BR / 7 BA / Sleeps 6

Holly Jewel-727 Holly Road - Holmes Beach vacation rentals
1 / 18

$172

Inquire

Holly Jewel-727 Holly Road

3 BR / 7 BA / Sleeps 6 | Quick view

Details

Welcome to Holly Jewel located at 727 Holly Road on the northern end of beautiful Anna Maria Island. This private and lovely three bedroom and 2 1/2 bath vacation rental features all that you will need to stay a week or a month! Feel the breezes through the lanai or lounge in the private yard along the mangrove …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$187

2 BR / 2 BA / Sleeps 4

Water's Edge 209 South - Holmes Beach vacation rentals
1 / 18

$187

Inquire

Water's Edge 209 South

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Welcome to the Water's Edge Condo complex in Holmes Beach, FL. Enjoy this direct gulf front 2 bedroom 2 bathroom condo with views that are among the best on the Gulf of Mexico. This condo was just completely re-done to the highest of standards and you will want to come back year after year. Enjoy the upscale …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$129

2 BR / 2 BA / Sleeps 6

Water's Edge 103 North - Holmes Beach vacation rentals
1 / 20

$129

Inquire

Water's Edge 103 North

2 BR / 2 BA / Sleeps 6 | Quick view

Details

DIRECT gulf front two bedroom and two bath condo in desirable Water's Edge complex which is the best place for a holiday rental. Enjoy the large heated pool and just steps to the Gulf of Mexico. Whether you stay a week or a month this is the perfect condo for a winter retreat, vacation rental or an island escape. …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$108

2 BR / 2 BA / Sleeps 4

1 / 15

$108

Inquire

Shore Birds-514 68th St

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Bay Palms canal home located at 514 68th ST. Holmes Beach, Anna Maria Island, FL -- (2) Bed: (2) Bath Accommodates up to (4) people: Internet - Highspeed: No smoking: Small dogs OK Kick back and relax in this charming 2 bedroom 2 bath island oasis!. Boaters will enjoy the dock on a wide, deep water canal that …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$129

2 BR / 6 BA / Sleeps 6

19 Reviews

$129

Inquire

Water's Edge 106 North

2 BR / 6 BA / Sleeps 6 | Quick view
“ Excellent ” 19 Reviews

Details

Reviews

(19)

DIRECT GULF FRONT CONDO WITH HEATED POOL1 Perfect family condo for a vacation holiday rental with a large heated pool and nestled right in the sands of the gulf beaches. You will find it quiet and peaceful whether you stay a week or a month - this is the perfect place for a winter retreat, beach rental or an island …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(19)

Nice Condo on Anna Maria

Left on Jul 30, 2008 for a stay in May 2008

This is called "Beach House 105" but it is not a house at all. It is a lower level condo of a two-story building. The amenities were very nice, as was the view. Location great also--recommend bicycles for fun (rent from the guy across from Island Property office near the intersection--he's way too nice). I did have an issue with a nosey permanent tenant (owner) close to us who promptly told me …

PreviousNext property

$146

1 BR / 6 BA / Sleeps 4

1 / 18

$146

Inquire

Water's Edge 205 South

1 BR / 6 BA / Sleeps 4 | Quick view

Details

Lovely Gulf Front Condo... Perfect get away condo for a holiday rental with a large pool and nestled right in the sands of the gulf beaches. Whether you stay a week or a month this is the perfect place for a winter retreat, beach rental or an island escape. There are so many island activities at your fingertips…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$158

2 BR / 2 BA / Sleeps 6

1 / 21

$158

Inquire

Serenity Now 6820 Gulf Dr.

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Welcome to West Winds Condo located at 6820 Gulf Drive, Holmes Beach, FL. This updated 2 bedroom 2 bathroom condo comfortably accommodates up to 6 guests. It is located in a quiet, small, Gulf front condo complex West of Gulf Drive, on beautiful Anna Maria Island. It is the perfect winter retreat condo for a family …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$170

2 BR / 2 BA / Sleeps 4

1 / 30

$170

Inquire

5200 Gulf Dr Unit 401S

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Enjoy a magical sunset in this well maintained Gulf of Mexico DIRECT beachfront Condo... Perfect get away condo. The large heated pool and nestled right in the sands of the Gulf of Mexico beaches. Enjoy a sunset right on your direct gulf front enclosed lanai. This unit accepts a one month stay or longer. There are …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$150

3 BR / 2 BA / Sleeps 6

1 / 26

$150

Inquire

Lazy Daze 512 74th ST

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Bay Palms canal home located at 512 72nd ST. Holmes Beach, Anna Maria Island, FL -- (3) Bed: (2) Bath Accommodates up to (6) people:Allows weekly rentals so bring your boat. Use the lift and dock. Kick back and relax in this charming 3 bedroom 2 bath island oasis!. Boaters will enjoy the dock on a wide, deep water …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$180

3 BR / 2 BA / Sleeps 6

1 / 29

$180

Inquire

Little Miss Magic-116 81st St

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Close to the Beach, classic, and cute!! Welcome to Little Miss Magic located at 116 81st Street on beautiful Anna Maria Island on the West Coast of Florida. Beach access is just 5 homes away, west of Gulf Drive and with no streets to cross. This newly remodeled ground level home is in the perfect location between the…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$171

3 BR / 2 BA / Sleeps 6

1 / 25

$171

Inquire

Promise Kept 206 76 ST

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Welcome to "Promise Kept" located at 206 76th Street in Holmes Beach on beautiful Anna Maria Island, Florida. This home is a restoration of an original vacation home to fully updated Florida codes and standards in all respects. This 3 bedroom 2 bathroom ground level vacation rental single family home awaits the …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$170

2 BR / 2 BA / Sleeps 6

1 / 14

$170

Inquire

Water's Edge 209 North

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Enjoy a magical sunset in this updated Gulf of Mexico DIRECT top floor beachfront Condo. Perfect family condo for a holiday rental with a large heated pool and nestled right in the sands of the Gulf of Mexico beaches. Enjoy a sunset right on your direct gulf front covered open lanai. Whether you stay a week or a …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$161

2 BR / 2 BA / Sleeps 6

9 Reviews

$161

Inquire

6407 Gulf Dr, Upstairs

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

Recently remodeled island duplex just steps to the pristine Gulf of Mexico beaches of Holmes Beach. This vacation rental has been lovingly remodeled, and furnished with everything you could desire for a trip to our little "Peace" of paradise. The light and bright interior will allow you to rest peacefully because …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(9)

Great for the Gulf of Mexico

Left on Jul 24, 2008 for a stay in April 2008

Wonderful, comfortable home in an ideal location close to the sea.

Only (slight) issues would be the lack of ensuite bathrooms and the condition of the BBQ tray. When we used it we cleaned it!.

PreviousNext property

$200

3 BR / 3 BA / Sleeps 8

4 Reviews

$200

Inquire

Minnie Cottage - 125 47th St

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

BRAND NEW "Coastal Cottage" Island Home located at 125 47th St Street, Holmes Beach, Anna Maria Island, FL -- (3) Bed: Queen sleeper (3) Bath Accommodates up to (8) people: Internet - Wireless: No smoking: No Pets. Pack n play and high chair are included. Fantastic private vacation rental home just a few houses …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Incredible!!

Left on Jun 26, 2012 for a stay in May 2012

Pictures don't do justice for this beautiful rental home! The large kitchen with an island was perfect for entertaining. The pool is large and beautifully landscaped--we spent more time in the pool than at the beach! ( Although the beach was a close walk. ) We rented kayaks for the week and just put them in the garage. It was a perfect week!

PreviousNext property

$141

2 BR / 2 BA / Sleeps 4

1 / 17

$141

Inquire

Sunset Beach Unit 204

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Enjoy this beautifully furnished and renovated direct Gulf front vacation rental condo with a heated pool beachside. This spacious two bedroom, two bath unit is perfect for your vacation enjoyment. The living room features nice comfortable furniture to sit around and relax after a long beach day! You might want…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$129

2 BR / 2 BA / Sleeps 6

1 Reviews

$129

Inquire

Starfish Beach Unit 3

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Star Fish Beach 3 - Anna Maria Island's premier upscale development offers this vacation rental condo for the discriminating vacationer only. Every detail has been taken care of with our guest's relaxation in mind. A heated pool in a tropical landscape offers an oasis to relax after a long day of walking for miles …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Perfect choice for AMI / Holmes Beach Vacation

Left on Jul 01, 2014 for a stay in June 2014

We stayed at the Starfish Beach 3 in June of 2014. This was a last minute booking (reserved a few hours before arriving) so we were very excited to get such a nice rental unit. The Starfish Beach rentals are a group of about four units, but the way it's laid out, each one almost seems a separate entity. For example, the door to each one is not visible from the other units. The pool has a nice …

PreviousNext property

$125

2 BR / 1 BA / Sleeps 6

3 Reviews

$125

Inquire

Hudson Bay

2 BR / 1 BA / Sleeps 6 | Quick view
“ Very Good ” 3 Reviews

Details

Reviews

(3)

Hudson Bay is located at 309 62nd Street in Holmes Beach on Anna Maria Island. This two bedroom one bath home features a private, heated pool in a tropically landscaped fenced backyard. This ground level home features a newly remodeled kitchen with an open floor plan. Free WIFI as well as expanded cable and free …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Not home away from home, but OK

Left on Apr 09, 2013 for a stay in March 2013

Very easy to rent from abroad. Island Vacation Properties know what they are doing! Easy access to the keys even on a Sunday.
The house - situated in a quiet neighbourhood - was small but functional. We especially liked the kitchen.
The outside furniture and the back patio close to the house, is in need of some serious upgrading.

PreviousNext property

$129

2 BR / 2 BA / Sleeps 4

3 Reviews

$129

Inquire

Sun Plaza West: 2BR Condo w/Tennis Courts near Beach

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Sun Plaza West, located in Holmes Beach on Anna Maria Island, is a fantastic get-away for the beach lover and tennis enthusiast! This two-bedroom, two-bath, end unit condo is located just steps to the white sand beaches of the Gulf of Mexico. This vacation rental features a large master suite with sliding glass doors…
  • Sauna
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - over five
  • Suitable for the elderly

Details

Reviews

(3)

Lovely stay at Sun Plaza West 101

Left on Jul 12, 2014 for a stay in June 2014

We stayed at Sun Plaza West for a week. The condo complex is very nicely maintained. The pool area is very nice with restrooms and lots of seating and umbrellas. The beach is a short walk and there are outdoor showers. We loved the storage room with chairs, umbrellas, beach toys and more. It was also a great place to store our ocean floats. We also liked the grocery carts for our use by the …

PreviousNext property

$115

2 BR / 2 BA / Sleeps 4

4 Reviews

$115

Inquire

Sunbow Bay 114

2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 4 Reviews

Details

Reviews

(4)

Sunbow Bay Condominium #114 located at 3705 East Bay Drive in Holmes Beach has everything you could need or want for a memorable vacation. Conveniently close to shopping and restaurants yet out of the way and quiet. Sunbow Bay offers two heated pools, tennis courts, elevators, undercover parking and every conceivable …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Sun & Fun

Left on Feb 23, 2009 for a stay in March 2007

Nice clean Property, would stay there again,
The Internet has allowed us to view properties,
Prices etc. before booking. Agents for our
rentals have been very helpful.

Note' We travel all over the North Americal
continent, if we are in the Bradenton Fl. area we will defentely look you up again.

Jim Branchfloer

PreviousNext property

$171

2 BR / 2 BA / Sleeps 4

1 Reviews

$171

Inquire

Gulf View: 2BR Beachfront Condo with Amazing View

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Once you open the door to this Gulf View, you will begin to relax. Restful and soothing beach colors throughout this two-bedroom, two-bath condo will encourage you to have a fabulous vacation on Anna Maria Island. The breathtaking view of the sparkling water through floor to ceiling windows in the open living area …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for the elderly

Details

Reviews

(1)

Oh, what a view!

Left on May 05, 2014 for a stay in April 2014

Gulf View was clean, comfortable and "homey". We had a great week there this april! The view is, no question, outstanding ! The condo was clean and comfortable, the beds were fine, bathrooms terrific, kitchen fully stocked with everything we needed. Great place !

PreviousNext property

$105

1 BR / 1 BA / Sleeps 4

15 Reviews

$105

Inquire

Palm Cay 1

1 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 15 Reviews

Details

Reviews

(15)

Palm Cay Condominium #1 is located at 3000 Gulf Drive in Holmes Beach, on the west side of the street for easy beach access. The complex offers a heated pool and an on site coin operated laundry room for your convenience. It’s a short stroll to shopping and restaurants and the beach is less than two minutes away. …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(15)

cozy, great location and affordable

Left on Feb 23, 2009 for a stay in April 2008

Nice home with a cozy feel. convienent location to beach and stores. Pool was clean and quiet. Nice layout and room to bq on side lawn. We rented bikes and biked the area never using our car. Clean, good size rooms and well kept property.Nice laundry area as well. Easy walk to the beach.
The busy road was a bit of a draw back since our unit fronted the road.

We would rent this unit again.

PreviousNext property

$129

2 BR / 1 BA / Sleeps 6

9 Reviews

$129

Inquire

Island Hideaway East: 2BR Kid-Friendly Pool Home

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

Island Hideaway East has been newly renovated for your vacation pleasure! Over 800 square feet of living area boasts a king master and a twin bedroom with a hall bath. The open and spacious living area includes a kitchen with granite countertops and stainless appliances. The kitchen opens onto an upper deck for …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Suitable for children - over five
  • Suitable for the elderly - ask

Details

Reviews

(9)

Fabulous

Left on Dec 01, 2010 for a stay in November 2010

We had a great time, AMI is such a wonderful place, great beaches, excellent food and amazing sun sets.

We thoroughly enjoyed our time at the villa, spending many hours in the pool with the children. We can honestly say that the master bed was the most comfortable we have ever slept in. The children absolutely loved the bar in the games room, My wife and I had poolside waiter service all day …

PreviousNext property

$158

2 BR / 2 BA / Sleeps 4

1 / 25

$158

Book

West Bay Pt Moorings Unit 64

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Enjoy one of the most breathtaking views on the island from this lovely two bedroom/two bath upstairs unit at West Bay Point Moorings. Not only are the views spectacular, but the entire complex is unique on Anna Maria, with large, open vistas, lush landscaping, four heated swimming pools, two outdoor jacuzzis, tennis…
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Fitness Room
  • Parking
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$120

2 BR / 2 BA / Sleeps 6

5 Reviews

$120

Inquire

Seacrest II Condos 4

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

Seacrest II Condo, Unit #4 at 3703 5th Avenue in Holmes Beach, is a very comfortably furnished and recently updated unit in a smaller complex, just a few short steps to the beach and located out of the way on a dead end street. Seacrest offers a heated pool, and every amenity to make your stay here a comfortable one. …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(5)

Spring Break with the Grandchildren!

Left on Mar 13, 2009 for a stay in March 2008

Every year my three grandchildren and I go somewhere warm for Spring Break. The last 3 years, we have enjoyed the beauty and restfulness of Anna Maria Island in Florida. Our stay at Seacrest II was delightful! The condo was clean and bright with lots of room for all of us. I thoroughly enjoyed the master bedroom with the wonderful walk in shower with shower heads at each end. We were in short…

PreviousNext property

$309

4 BR / 3 BA / Sleeps 8

2 Reviews

$309

Inquire

SIMPLY CHIC

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Beautiful, Brand New, Ground Level 4 bedroom/3 bath home, just a short block to the beach. Beautiful back yard with Heated Pool surrounded by a large paver deck and beautiful outdoor dining and gas grill area by pool. Open Living/Family/Dining Room area for everyone to gather, and attention to the smallest details …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

2 Weeks in Paradise.

Left on Oct 18, 2013 for a stay in June 2013

Simply Chic more than lived up to it's name.Spacious,well laid out,beautifully furnished,fabulous garden, great pool,ideally located(short stroll to the beach and bus stop)quiet location and truly excellent value for money.

I would not hesitate to re-book anna Maria accommodations managed the booking and the holiday superbly. They are highly recommended.

PreviousNext property

$235

3 BR / 3 BA / Sleeps 8

1 / 22

$235

Inquire

Beachside

3 BR / 3 BA / Sleeps 8 | Quick view

Details

The Beachside is a custom built three bedroom, two bath pool home located at 113 31st Street in Holmes Beach. This spectacular home is west of Gulf Drive for easy beach access with no busy streets to cross. The pool area is tropical and spacious with a charcoal grill for you enjoyment. It’s surrounded by swaying …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$120

2 BR / 2 BA / Sleeps 6

16 Reviews

$120

Inquire

Seacrest II Condos 1

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 16 Reviews

Details

Reviews

(16)

Located in the heart of Anna Maria Island, at 3703 5th Avenue, in the sun-drenched community of Holmes Beach this roomy two bedroom, two bathroom condo is a recently up-dated, re-decorated and well maintained roomy, light and airy unit with covered parking plus a heated pool. Leave the car at home because this small …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(16)

Great Island Getaway!!

Left on Feb 23, 2009 for a stay in May 2008

We had a WONDERFUL stay in this condo! My family came down for my daughter's graduation; it was a perfect place - close to Bradenton, but with the island feel. It was great being so close to the beach, and the pool was nice and private. The condo was lovely - all the necessities, lots of extras, and everything was top-notch. The beds were very comfortable, and we spent lots of time on the …

PreviousNext property

$180

2 BR / 2 BA / Sleeps 4

2 Reviews

$180

Inquire

ISLAND GIRL WEST

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Tropical, quiet, 2 bedroom/ 2 bath duplex, just over a block to the beach, and a block to the free Island trolley! Elevated, with one car garage underneath filled with beach chairs and wagon. Heated Pool surrounded by a large paver deck, lush landscape and plenty of seating. Sleeps up to 4. 1160 Sq. ft. Island …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Relaxing

Left on Mar 01, 2014 for a stay in October 2013

ap artment was large and clean. The pool and surrounding plants

are beautiful. Island Girl is close to restaurants and some

shopping. I would love to go again .

PreviousNext property

$332

3 BR / 4 BA / Sleeps 12

17 Reviews

$332

Inquire

Harrison Home

3 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 17 Reviews

Details

Reviews

(17)

The Harrison Home is a very spacious three bedroom, four bath pool home located at 6901 Gulf Drive in Holmes Beach, just 150' to a beautiful sandy beach. Located in the preferred northern end of Holmes Beach, this home features a private pool with fenced yard, poolside gazebo, extensive new landscaping, single car …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(17)

great house

Left on Feb 23, 2009 for a stay in March 2008

We had a wonderful stay. The pool was fabulous and it was only a
short walk to the beach. This was our 4th trip to Anna Maria and this
was our favorite rental thus far.

PreviousNext property

$274

3 BR / 2 BA / Sleeps 6

1 / 33

$274

Inquire

BAY SERA

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Come to this Island home and "Whatever will be, will be!" Remodeled and tasteful is this 3 bedroom/2 bath home with new heated pool and hot tub in a very private backyard setting. Well appointed with designer finishes throughout. The kitchen is outfitted with gorgeous granite countertops and stainless steel applicanes…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$264

4 BR / 3 BA / Sleeps 8

3 Reviews

$264

Inquire

Twin Heron: 4BR Family-Friendly Pool Home

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

This brand new and beautifully furnished four-bedroom, 3.5-bath vacation rental is just over a block to the beach! With a large great room layout and balconies in front and back of the house there is plenty of room for vacationing in this Anna Maria Island home. The master bedroom on the main floor has a king-sized …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Suitable for children - over five
  • Suitable for the elderly - ask

Details

Reviews

(3)

Twin Heron on Anna Maria Island is very relaxing.

Left on Aug 25, 2014 for a stay in August 2014

We enjoyed our stay at Twin Heron on Anna Maria Island. This is a very nice, spacious and clean rental property that has all the upscale comforts of home. Scenic grounds well maintained. Short walk to the beach and even an island trolley is available. Recommend dining on the porch of the "Waterfront Restaurant" with great views of Tampa Bay. Coastal Cottages AMI is a professional vacation rental …

PreviousNext property

$342

4 BR / 4 BA / Sleeps 13

1 Reviews

$342

Inquire

Island Bay House Both

4 BR / 4 BA / Sleeps 13 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

The Island Bay House is a glorious four bedroom four bathroom bay front duplex located at 232 South Harbor Drive in Holmes Beach. This spacious duplex features an elevator, boat dock, heated indoor pool and spa. This property features spectacular panoramic views of the Intracoastal and Tampa Bay from almost every room…
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

It was a incredible view.

Left on Apr 24, 2014 for a stay in April 2014

I've never reserved anything on line before. When we pulled up to the house we got excited and when we got into the house my son give me the high 5 thumbs up. There were 3 families and we took 5 high school seniors for there senior trip. It was a great house, with plenty of space for all of us. The only negative things were, there could of been more water in the pool, and maybe a little …

PreviousNext property

$120

2 BR / 2 BA / Sleeps 6

16 Reviews

$120

Inquire

Seacrest II Condos 3

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 16 Reviews

Details

Reviews

(16)

Seacrest II Condo, Unit #3 at 3703 5th Avenue in Holmes Beach, is a very comfortably furnished and recently updated unit in a smaller complex, just a few short steps to the beach and located out of the way on a dead end street. Seacrest offers a heated pool, and every amenity to make your stay here a comfortable one. …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(16)

Needs some work

Left on Feb 25, 2009 for a stay in July 2008

This condo needed a lot of minor repairs. Every window treatment in the unit was broken. There was a bug infestation in the kitchen. Master bedroom mattress-very uncomforable(no mattress pad on mattress also) Light in pool kept falling out. No screens on lanai-other condos had them.

condo was for sale--not a desirable way to sell a property! Would not rent this condo again!

PreviousNext property

$115

2 BR / 1 BA / Sleeps 6

14 Reviews

$115

Inquire

Sea Pirate 3

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 14 Reviews

Details

Reviews

(14)

Sea Pirate Condo #3, located at 3301 Gulf Drive in the heart of Holmes Beach is just a stone's throw from the tropic teal waters of the Gulf of Mexico. Situated in a much desired area, close to shopping and restaurants, this smaller complex features a large, screened and heated pool, on site coin operated laundry …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(14)

Fun on the beach

Left on Jan 27, 2011 for a stay in January 2011

The condo was very clean, nicely decorated, adequately furnished with everything we needed. Would love to stay there again sometime.

PreviousNext property

$161

2 BR / 2 BA / Sleeps 4

1 / 1

$161

Inquire

Astounding gulf views from both bedrooms in this remodeled Condo

2 BR / 2 BA / Sleeps 4 | Quick view

Details

5400 Gulf Drive Condominium complex located in the preferred and quieter northern end of Holmes Beach. Come experience amazing views from this quiet complex. You have beautiful partial views of the unspoiled, powder soft, white beach and sparkling Gulf waters from the large lanai off of the living room area …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$175

2 BR / 2 BA / Sleeps 4

2 Reviews

$175

Inquire

Playa Encantada 112

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Playa Encantada 112 is a gorgeous two bedroom, two bath direct Gulf front complex, located at 6006 Gulf Drive in Holmes Beach. This popular complex features an elevator, heated pool, jacuzzi, 2 tennis courts and shuffle board. The open balcony gives you a view of the gulf.The living room features a 32” flat …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great location. Very relaxing.

Left on Aug 01, 2013 for a stay in July 2013

Very nice and relaxing family vacation. Ideal for families with young kids. All the amenities of home just steps to the beach. Will definitely return.

PreviousNext property

$121

2 BR / 2 BA / Sleeps 6

1 / 9

$121

Inquire

Sunbow Bay #203

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunbow Bay unit #203 is close to shopping and restaurants; yet out of the way and quiet. This unit is very comfortably furnished and overlooks a natural bayou. Sunbow Bay offers two heated pools, tennis courts, an elevator, covered parking, and a long boardwalk and fishing pier that puts you at the threshold of Anna …
  • Waterfront
  • Ocean or water views
  • A/C or climate control
  • Central heating
  • Patio
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$115

1 BR / 2 BA / Sleeps 4

4 Reviews

$115

Inquire

Seaside Beach House 102

1 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Seaside Beach House #102 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a heated pool at beachside. It’s one of the nicest complexes on Anna Maria Island. This "hidden away" property is located on a quiet side street in the northern end of Holmes Beach. The beach stretches for miles …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Everything I hoped would be.

Left on Mar 02, 2011 for a stay in February 2011

The condo was well furnished and in a quiet neighborhood. The beach was convenient and beautiful Will definitely plan on going back.

PreviousNext property

$274

3 BR / 2 BA / Sleeps 6

1 / 34

$274

Inquire

BEACHWALK

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Three bedroom, two bath totally redone home with gorgeously landscaped backyard and heated pool! Only houses to the Gulf of Mexico and a beautiful white sand stretch of beach! This home has been updated with Mexican tile, granite countertops, and stainless kitchen! King-sized master bedroom, second queen-sized bedroom…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$144

1 BR / 1 BA / Sleeps 4

26 Reviews

$144

Inquire

Alamanda Villas 5

1 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 26 Reviews

Details

Reviews

(26)

Alamanda Villas, located at 102 39th Street in Holmes Beach is a charming beachside complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area. Anna Maria's white sandy beaches and the emerald green water of the Gulf of Mexico are just outside your door to …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(26)

RIGHT ON THE BEACH

Left on Feb 23, 2009 for a stay in October 2008

A great place for a couple to stay, in a wonderful part of the world. unfortunately the weakness of the British currency will defer most Uk citizens from returning in 2009.

PreviousNext property

$171

3 BR / 2 BA / Sleeps 6

1 / 15

$171

Inquire

Sea Breeze Pool Home

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Sea Breeze is a private home with 3 bedrooms and 2 bathrooms and a brand new heated pool! The home is comfortable and well stocked. Wood floors throughout, open floor plan and cathedral ceilings with large sliders that open onto a large screened porch. Close proximity to the beach, about 3 blocks. Located in …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$266

4 BR / 3 BA / Sleeps 11

1 / 22

$266

Inquire

SS Salamander Both units

4 BR / 3 BA / Sleeps 11 | Quick view

Details

Welcome to the SS Salamander located at 121 50th Street in Holmes Beach. This recently updated duplex is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's easily within walking distance to restaurants and shopping…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$229

3 BR / 3 BA / Sleeps 6

5 Reviews

$229

Book

A Pearl of a Beach Home with private Pool & Spa

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

*** LARGE HEATED FREE-FORM, LUXURY POOL AND SPA WITH SPACIOUS PAVED SURROUND - AVAILABLE FROM AUGUST 2014 - TOGETHER WITH TROPICAL LANDSCAPING, AUTOMATED GARDEN LIGHTING AND LARGE GROUND FLOOR LANAI. *** Leave your troubles behind as you cross to Anna Maria and surrender to the island pace. Our beach house (a …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(5)

Best vacation in 40 years!

Left on Mar 05, 2014 for a stay in February 2014

The owners, Mike and Lesley Crowther were wonderful to deal with

before, during and after our two week stay at their home. The house

was immaculate and had everything we could have needed during our

stay. Large bedrooms and baths with excellent beds and showers. The

kitchen and laundry room appliances were all in new condition. We

found ourselves wanting to eat in most of the time as the …

PreviousNext property

$115

2 BR / 2 BA / Sleeps 4

1 / 22

$115

Inquire

Sunbow Bay 302

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Sunbow Bay Condominium #302 located at 3705 East Bay Drive in Holmes Beach has everything you could need or want for a memorable vacation. Conveniently close to shopping and restaurants yet out of the way and quiet. Sunbow Bay offers two heated pools, tennis courts, elevators, undercover parking and every conceivable …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$120

2 BR / 2 BA / Sleeps 6

2 Reviews

$120

Inquire

While Away

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

The While Away, located at 6203 Holmes Blvd. in Holmes Beach is a two bedroom, two bath, ground level duplex with a private heated pool. This very spacious duplex is located in a quiet, residential neighborhood just a short stroll to the beach, shopping or the library. It’s a perfect spot to relax, unwind and …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Overall OK

Left on Aug 21, 2014 for a stay in July 2014

The property was clean and we'll kept. The AC had trouble maintaining a constant, comfortable temp during the day. We arrived on Thursday and discovered on Friday night that the washing machine was broken. We reported the problem to property management on Saturday and to their credit, they had someone out they same day; however, it wasn't fixed until the following Tuesday.

About a 5 minutes …

PreviousNext property

$135

3 BR / 2 BA / Sleeps 6

4 Reviews

$135

Inquire

Palm Cay 5

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Palm Cay 5 located at 3000 Gulf Drive in Holmes Beach is a very spacious three bedroom, two bath town home located west of Gulf Drive for easy beach access. The complex features a very large heated pool and onsite laundry room. The complex is about one half block to the beach and is very convenient to shopping and …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

We had a wonderful stay, in a great location, and in a spacious

Left on Jul 26, 2012 for a stay in July 2012

We loved the rental property! It was very rencently renovated and the owners must take pride in their property, as they have selected stunning appointments, materials, and finishes for the unit, certainly blowing the majority of its competitors out of the water since most investors merely choose the cheapest and standard "rental" quality materials and finishes. The property is very spacious, …

PreviousNext property

$156

3 BR / 3 BA / Sleeps 6

1 Reviews

$156

Inquire

Key Largo Cottage

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Key Largo Cottage 315 62nd St. Holmes Beach, Fl. 34217 Step into Key Largo Cottage and feel the sun-drenched, tropical ambience. This newly-constructed cottage has a heated pool complete with swim-up table and waterfall surrounded by lush foliage which creates a private backyard oasis. The inside has beautiful …
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Can't wait to go back

Left on Jul 22, 2014 for a stay in July 2014

Anna Maria Island is our new destination. Great place for families traveling with kids of all ages. House was in a great location. Easy 5 min walk to the beach made even easier with the provided metal cart. Toss all your stuff in there and go. Beach is very clean and deep. Great shelling and watch out for the sea turtle nests which are clearly marked.

Comfortable beds, well equipped …

1 23456
page 1 of 9
Load more