50 Best Holmes Beach Vacation rentals on Holiday Lettings - House rentals

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1,603 Vacation rentals

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

(2) Excellent 

21

Condo rental in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The number 3 island in the United States so says Trip Advisor. The best island beach sand so says Conde Nast Travelers. So who wouldn't want to stay right on the beach in an immaculate and roomy 2 bedroom, 2 bath condominium in the Tiffany Place Condominium located on …see more

from $179 / night

$1,250 / week

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from $179 / 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

(2) Excellent 

20

Apartment rental 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 0.6 mi
  • Ask about children
Totally furnished apartment close to the beach. Spend quality time in a nice neighborhood. Enjoy activities such as playing tennis, kayaking, water skiing, fishing, painting, swimming, walking your dog and meeting new people at the dog park , the library or the Communit …see more

from $129 / night

$900 / week

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from $129 / night

(5) Very Good 

14

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
LaPlayita 5 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 6 people. Unforgetable Vacations Created Here!~ Vaulted Ceiling in Living Room. Upper Level Master Bedroom/Bath. Lower Level Bedroom/Bath. Telephone, Cable TV, wi-fi internet service available. Fully Furnis …see more

from $115 / night

$800 - $1,540 / week

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from $115 / night

(5) Excellent 

27

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 0.3 mi
  • Child friendly
This property is available for rentals 7 nights or more. 99 steps from the beach! Elegantly furnished two bedroom and two bath condo with brand new Tommy Bahama style furnishings. Sit by the heated pool after a stroll on the white, sandy beach of Holmes Beach just acr …see more

from $193 / night

$1,500 - $1,780 / week

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from $193 / night

(22) Excellent 

Certificate of Excellence

32

Vacation home accommodation

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
**DISCOUNTS FOR RENTALS OF 28 NIGHTS OR MORE ANY TIME OF YEAR** *****PLEASE ASK US ABOUT SPECIAL PRICING FOR YOUR STAY***** LARGE HEATED FREE-FORM, LUXURY POOL AND SPA WITH SPACIOUS PAVED SURROUND - ADDED AUGUST 2014 TOGETHER WITH TROPICAL LANDSCAPING, AUTOMATED GAR …see more

Certificate of Excellence

from $229 / night

$1,600 - $2,500 / week

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from $229 / night

(14) Excellent 

37

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
5 reasons why you will love our condos as much as we do: *LOCATION! Close to the beach, grocery store, restaurants and everyday needs. 'We really appreciate not having to use a car to buy milk. Also, with several restaurants within half a mile, it's so n …see more

from $143 / night

$999 - $2,150 / week

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Responds fast!
avg. 1 hour 3 minutes

from $143 / 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

(3) Excellent 

23

Vacation home with shared pool in Holmes Beach

Anna Maria Island / Holmes Beach

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
510 Bayview - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. Island Elegance for the whole family!~ Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and surf. …see more

from $494 / night

$3,500 - $6,000 / week

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from $494 / night

(2) Excellent 

31

Vacation cottage with swimming pool in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This newly remodeled Florida gem backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably priced, this quaint 3 bedroom, 1 bath cottage has a spacious backyard equipped with a pool, hammock, patio furniture, grill, brick fir …see more

from $225 / night

$1,240 / week

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from $225 / night

27

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Sandy Point 111 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000289 Condo in quiet, residential area about 4 blocks to the beach. Walking distance to grocery, shops and restaurants. Laundry in unit. Overlooks mangroves. Heated pool. Anna Mari …see more

from $135 / night

$700 - $1,430 / week

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from $135 / night

14

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 0.1 mi
  • Child friendly
Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel applia …see more

from $150 / night

$888 - $2,375 / week

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Responds fast!
avg. 2 hours 7 minutes

from $150 / night

29

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
5801 DePalmas - Private home 3 Bedroom / 2 Bath , maximum occupancy of 6 people. Comfy and Cozy Florida Living!~ Cute cozy ground level home 3 Bedroom/ 2Bath close to the beach on a quiet dead end street. Fully furnished with linens towels, cooking utensils, basic …see more

from $128 / night

$890 - $1,089 / week

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from $128 / night

(4) Very Good 

23

Vacation apartment rental

Anna Maria Island / Holmes Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Horizon West 112 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 4 people. VRC16-000683 Beach Bound.....This is your place!~ 2 bedroom 2 bath condo 1 very short block to beach. Beautifully decorated with comfortable furniture. Everything you need for a relaxing vac …see more

from $115 / night

$730 - $1,500 / week

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from $115 / 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

27

Vacation condo in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Cast Villa sits in the heart of Anna Maria Island directly across from the famous Manatee County public beach W/life guard which features a gift/surf shop, restaurant, Tiki bar, live music and more. Beach is groomed daily and has lifeguards. Walk to Publix grocery s …see more

from $175 / night

$1,480 - $1,550 / week

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from $175 / night

23

Vacation villa in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Air conditioning
Lush tropical landscaped setting. Beautifully maintained two bedroom vacation rental on gorgeous Anna Maria Island. Secluded beaches, shopping, restaurants, golf, fishing and relaxation. Apartment includes full kitchen, 50' flat screen TV in living room, flat screen TV …see more

from $136 / night

$950 / week

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from $136 / night

(3) Very Good 

13

Cottage rental in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This cottage is located "on the beach" 3007 Avenue F, beautiful Holmes beach. It is the downstairs unit (1 of 2). The cottage is very comfortable and sleeps 4 comfortably with additional space for a pull-out. This quaint cottage is hidden away on a dead end street …see more

from $180 / night

$1,140 / week

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Responds fast!
avg. 1 hour 59 minutes

from $180 / 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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Responds fast!
avg. 3 hours 27 minutes

from $135 / night

34

Vacation apartment with shared pool in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
West Bay Cove 222 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. West Bay Cove is a great location for taking advantage of everything that Anna Maria Island has to offer. Only a block from the public beach area, close to the grocery store, several shops …see more

from $87 / night

$900 / week

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from $87 / night

(2) Excellent 

21

Vacation townhouse in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool
Newly Remodeled & Professionally Decorated Large Townhome in Desirable North Beach Village, one Block from beautiful White Sand Beaches. Brand new Upscale Furnishings in all Rooms. Big Flat Screen Smart TV's in all rooms with Premium HD Cable & WiFi powerful enough to …see more

from $225 / night

$1,500 - $2,500 / week

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from $225 / night

(2) Very Good 

16

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
3011 Ave E-1 - Triplex Condo 4 Bedroom/ 2 Bath , maximum occupancy of 8 people. VRC16-000050 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 gues …see more

from $200 / night

$1,350 - $2,100 / week

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from $200 / 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

21

Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 60 nights min

  • 2 bedrooms
  • Sleeps 6
  • 60 nights min
  • Child friendly
This newly decorated and refurbished condo is the answer to your dreams this fall. This 2 bedroom 1.5 bath condo is 300 steps to the beautiful white sands and crystal blue waters of Anna Maria Island. The condo is completely turn-key ready--nothing to bring but your swi …see more

from $90 / night

$630 / week

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from $90 / 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 8 minutes

from $200 / 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

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

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

24

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
Bright and light condo on the second floor with view to the Palma Sola Bay (left side) and a peek-a-boo-view to the beach (right side) but only some steps away from the blue green water of the Gulf. 7 miles of white sandy beaches invite you for walking, swimming or only …see more

from $100 / night

$650 - $1,400 / week

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from $100 / night

(2) Excellent 

22

Holmes Beach Vacation cottage rental

Anna Maria Island / Holmes Beach

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.02 mi
  • Swimming pool
ANNA MARIA ISLAND #3 TOP 10 ISLAND'S IN U.S.A. Palm Isle 3203,our 2 bedroom island decorated condo is across the street from the beaches of Anna Maria Island. Steps from the heated pool and fully landscaped setting, along with all the amenities of home, your fa …see more

from $199 / night

$1,300 / week

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Responds fast!
avg. 1 hour 3 minutes

from $199 / 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

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

(2) Very Good 

18

Holmes Beach Vacation condo rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This two bedroom, two-bath condo has been tastefully renovated and refurbished. The kitchen has new appliances and granite countertops. All the new furnishings make this a very comfortable home away from home. It has a private screened balcony off the living room and b …see more

from $130 / night

$900 - $1,050 / week

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from $130 / night

18

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Recently updated two bedroom two bath condo located at Runaway Bay. Property has the largest pool on Annamarie Island. Walking distance to excellent restaurants and beach. Offers a view of the bay. Tennis court and shuffleboard on site. It is an upstairs unit. …see more

from $125 / night

$800 - $1,200 / week

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from $125 / night

12

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Old Florida charm in a completely remodeled house only 1 1/2 short blocks to an uncrowded beach. Ours is a 2 bedroom/2 bath home which sleeps 5. It is the larger 1/2 of a duplex house with exclusive use of the solar heated saltwater pool in the privately fenced backyard …see more

from $208 / night

$1,450 / week

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Responds fast!
avg. 1 hour 10 minutes

from $208 / night

17

Vacation condo in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
Three bedroom condo directly overlooking the Gulf of Mexico. Watch the dolphins while eating your breakfast or the beautiful Gulf sunsets over wine or while eating dinner. Master bedroom has a king size bed and en suite bathroom with shower and walk-in closet. Second …see more

from $185 / night

$1,295 / week

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from $185 / night

(2) Excellent 

15

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
  • Child friendly
  • Air conditioning
Come relax and enjoy your beach vacation at The Dolphin Club! 2 bedrooms and 1 bathroom, the master bedroom has a queen bed and the other has 2 twin beds. There is also a sleeper couch in the living room which can sleep 2 people. Fully air conditioned. Includes covered …see more

from $110 / night

$700 - $1,200 / week

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Responds fast!
avg. 1 hour 13 minutes

from $110 / night

11

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Sandy Point 205 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. VRC16-000291 Sit on your balcony and listen to the gentle sway of the mangroves as you sip on your cocktail and bask in the Florida warmth! 2 bedroom, 2 bath condo in quiet, residential area abo …see more

from $135 / night

$700 - $1,430 / week

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from $135 / night

24

Holmes Beach Vacation home rental

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0.4 mi
  • Child friendly
  • Air conditioning
Authentic spacious beach cottage charm in a mid-century shell. Located a couple blocks from Florida's best powder sand beach and situated across from Bimini Bay with use of our dock. Explore the quiet paradise where the locals live. The Pine Ave shops and famous Beach B …see more

from $214 / night

$1,500 - $1,890 / week

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Responds fast!
avg. 3 hours 40 minutes

from $214 / night