We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Holmes Beach, FL

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 394 Rentals in Holmes Beach
loading...
Sort by
From
$165
Per Night
1 / 20
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
From
$150
Per Night
1 / 21
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
From
$143
Per Night
1 / 28
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (5) Make Inquiry
From
$100
Per Night
1 / 23
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (20) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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 offer three locations on... View all property information
Make Inquiry
5 of 5 stars Reviewed August 31, 2014
Everything was perfect on our stay at Ohana North. We had a great time being close to the beach. The place was clean and thoughtfully stocked with things like beach chairs...
5 of 5 stars Reviewed July 17, 2014
This condo is just outstanding, from the decor/amenities to the location. Danny has made sure you have EVERYTHING you need to enjoy your stay. It was very clean and charming. It...
See all reviews
From
$98
Per Night
1 / 45
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (14) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Cove at Sandy point, unit 204 ,3601 East Bay drive, Holmes Beach is a beautiful upper floor, fully air conditioned 2 bed, 2 baths Pool front condo that has been completely remodeled and entirely refurnished in May 2012. Situated near a quiet nature reserve it also benefits from being just a... View all property information
Make Inquiry
5 of 5 stars Reviewed September 21, 2014
Stayed here from the 3rd September to the 12th September. Lorraine is the nicest person to deal with. The condo was perfect. We travelled as a family, me, hubby, daughter aged 15...
5 of 5 stars Reviewed January 4, 2014
We stayed at this wonderful condo over Christmas 2013. I was as described, a short walk to Publix and to beach. The bus stops outside Publix,so there is no need to use your...
See all reviews
From
$243
Per Night
1 / 25
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
** SPECIAL ** Receive $200 off your base rental fee on October and November 2014 stays! When booking, mention or use the promo code STARFISH. With breath-taking views of the Gulf of Mexico from almost every room and just steps to the beach, you may never want to leave the soothing and relaxing... View all property information
Make Inquiry
From
$150
Per Night
1 / 19
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
One bedroom one bath condo located 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 and kitchen sleeps up to 4. There are... View all property information
Make Inquiry
4 of 5 stars Reviewed September 2, 2014
Yes, the room was very dated, as the pictures showed. It would seem for $200 a night, an upgrade in furnishings is due. But, it was clean, and the short walk to the beach made...
See all reviews
From
$193
Per Night
1 / 31
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
*** 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... View all property information
Make Inquiry
5 of 5 stars Reviewed July 19, 2014
This home looked great from the online pictures but was even nicer in person. Mike and Lesley went out of their way to accommodate our young family by purchasing a highchair and...
5 of 5 stars Reviewed March 16, 2014
we should declare an interest in that Mike and Lesley are long standing friends nevertheless this is, the website suggests a jewel of a property. We had a week with my husband's...
See all reviews
From
$100
Per Night
1 / 15
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Seaside Gardens 460 63rd Street Holmes Beach, Fl 34217 This lovely canal front, ground level, attached bungalow offers fantastic views and amenities! Enjoy the shared deep water dock right off of your backyard, community tennis courts, private ping-pong table, board games and so much more! This... View all property information
Make Inquiry
From
$86
Per Night
1 / 8
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
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 2 blocks away with its bright white sand and aquamarine waters. For... View all property information
Make Inquiry
Get the List
From
$142
Per Night
1 / 22
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (11) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
6 reasons why you will love our condos as much as we do: *VIEW! So close to the beach, with a wonderful view from the living room and master bedroom - not to mention from the roof-top terrace! *LOCATION! Close to the beach, grocery store, restaurants and everyday needs. 'We really... View all property information
Make Inquiry
From
$200
Per Night
1 / 18
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Pool
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
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 to 4. There are two double... View all property information
Make Inquiry
5 of 5 stars Reviewed July 21, 2014
Our stays here have always been enjoyable & awesome. Really nice comfortable condo unit & being right on the beach......you can't ask for anything more!!!! Even the Sea Turtles...
See all reviews
From
$193
Per Night
1 / 27
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
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 across the street! There are 18... View all property information
Make Inquiry
From
$170
Per Night
1 / 52
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (9) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A brand NEW 2300 sq/ft, 3 bedroom modern beach house with heated and very private pool. A perfect location just steps from the beach, marina and the main plaza with great shops, a grocery store and restaurants. No need to drive anywhere. Located in a quiet neighborhood with tropical greenery, large... View all property information
Make Inquiry
5 of 5 stars Reviewed October 29, 2014
We had a great time and the house was perfect. Our group was two families with 5 young children and 4 adults. Plenty of room in the house and everyone loved the pool. Alex was...
5 of 5 stars Reviewed September 10, 2014
We stayed in the house for a 4th of July holiday. The house is very well kept and had ample room for 4 adults and 3 children. The house is located a short walk from the beach...
See all reviews
From
$107
Per Night
1 / 10
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 2
Details Make Inquiry
Amenities & Details
  • Dishwasher
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This property can only accept 7 nights stays with a check-in on Saturday Anna Maria Island's newest and finest condominium complex offers several fabulous holiday villas all designer decorated and with floor plans maximizing water views. A heated pool is a great place to relax after a day at the... View all property information
Make Inquiry
From
$175
Per Night
1 / 22
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This is no ordinary rental! It is elegant, immaculate with upscale furnishings & very private while in one of the best locations on the Island! No car necessary while staying in this 1/1 apartment with optional 2nd bedroom (please inquire for availability). Second queen bedroom available for $75... View all property information
Make Inquiry
5 of 5 stars Reviewed July 21, 2014
We spent a fun-filled week at this property. We loved being steps away from this gorgeous beach where the sunsets are amazing. The apartment was spotless and well maintained...
See all reviews
From
$175
Per Night
1 / 10
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Beautiful Condo just steps from the white sandy beach!. Spacious 2 bedroom/ 2 Bath with partial views from the rear lanai. Tastefully decorated and a fully stocked kitchen make this your home away from home!. Unobstructed views from the rooftop deck make for spectacular sunsets. Master bedroom has... View all property information
Make Inquiry
1 of 5 stars Reviewed July 28, 2014
On 7/19/14 we checked in and found the condo had not been cleaned and all of the linens were on top of the washer and were all dirty. We had to start by sweeping floors, cleaning...
See all reviews
From
$485
Per Night
1 / 19
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
La Plage 2 is Island luxury at it's finest. An exquisite example of Mediterranean architecture nestled right on the sands of the Gulf of Mexico, this beachfront enclave will exceed all your expectations. Relax in the tropical splendor of this ultra-luxurious beachfront property on Anna Maria Island... View all property information
Make Inquiry
From
$150
Per Night
1 / 14
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Beach
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
One bedroom one bath condo located 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 and kitchen sleeps up to 4. There are... View all property information
Make Inquiry
From
$770
Per Week
1 / 17
2 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Hammock Haven is a wonderful two bedroom two bath home located at 2702 Avenue C in Holmes Beach. This two story beach get away has a distant gulf view and a peek at the bay. Hammock Haven is close to dining, beach, trolley, and the bay. Stroll the beaches, fish the bay, and explore the many... View all property information
Make Inquiry
From
$319
Per Night
1 / 14
Payment Protection
3 Bedrooms, 4 Bathrooms, Sleeps 9
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
200 feet from the Gulf Beach-Dead End Street. 2200 sqft of air conditioned luxury, 3 Bedroom, 3.5 Bath, All 3 bedrooms have private bath with walk-in shower. Deluxe kitchen with double fridge, wine fridge, double oven, microwave, dishwasher, water distiller and well equipped to cook Thanksgiving... View all property information
Make Inquiry
From
$442
Per Night
1 / 25
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island Paradise is just that- the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any better than this. It is like you are sitting on the deck of a cruise... View all property information
Make Inquiry
From
$150
Per Night
1 / 14
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
One bedroom one bath condo located 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 and kitchen sleeps up to 4. There are... View all property information
Make Inquiry
From
$725
Per Night
1 / 12
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Luxury at Anna Maria Island La Plage 2 6402 Gulf Drive Unit 2 Holmes Beach, FL 34217 La Plage 2 is Island luxury at its finest! An exquisite example of Mediterranean architecture nestled right on the sands of the Gulf of Mexico, this beachfront enclave will exceed all your expectations. Relax... View all property information
Make Inquiry
From
$291
Per Night
1 / 40
4 Bedrooms, 3 Bathrooms, Sleeps 12
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Very spacious 4 bedroom/3 bath home, just a short block to the beach (just over 100 yards), and a couple houses to the free Island trolley! Beautifully tropical landscaped back yard with a Heated Pool surrounded by a large paver deck and plenty of seating options. Huge open Living/Family Room area... View all property information
Make Inquiry
From
$165
Per Night
1 / 16
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Beach
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
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 up to 4. There are two... View all property information
Make Inquiry
From
$96
Per Night
1 / 25
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The perfect spot for the budget-conscious, beach-loving vacationer! This comfortable and clean 2 bedroom/2 bath elevated duplex is only 200 yards from the fabulous white sand beach and crystal-clear waters of the Gulf of Mexico! If rising vacation rental prices have you worried, this is your... View all property information
Make Inquiry
From
$200
Per Night
1 / 15
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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 to 4. There are two double... View all property information
Make Inquiry
From
$2,000
Per Week
1 / 25
Payment Protection
4 Bedrooms, 4 Bathrooms, Sleeps 9
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Wrap yourself in luxury in this owner/designer decorated home offering every amenity to make your trip to paradise a memorable experience. Gaze out from your bedroom balcony to the calming view of the canal. This home is a boater's delight, so bring your boat and enjoy the beautiful gulf waters.... View all property information
Make Inquiry
From
$286
Per Night
1 / 51
6 Bedrooms, 4 Bathrooms, Sleeps 16
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
*** Ask about our specials through the end of the year!! *** The world-famous Old Florida charm of Anna Maria meets brand-new, modern living in Villa Chianti, our latest FABULOUS vacation rental. 6 Bedrooms, sleeps 14. Villa Chianti boasts one of the largest beach entry pools on the island with... View all property information
Make Inquiry
From
$1,050
Per Week
1 / 12
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This cottage duplex is in a great location for all that Anna Maria offers. It is only a few blocks from the beautiful Gulf beaches and is convenient for catching the trolley or heading to any of the shops or restaurants on the island. After a great day on the beach relax in the living room with... View all property information
Make Inquiry
From
$165
Per Night
1 / 15
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Private Beach
  • Shared Outdoor Pool...
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
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 up to 4. There are two... View all property information
Make Inquiry
From
$471
Per Night
1 / 11
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
This luxurious 3 bedroom, 2 1/2 bathroom unit features Direct Gulf front, high floor views, making this one of the most spectacular condos on Anna Maria Island. The interior has deep cherry wood island style furniture, granite countertops, imported tiles, designer kitchen, crown molding and... View all property information
Make Inquiry
From
$485
Per Night
1 / 24
Payment Protection
3 Bedrooms, 7 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
La Plage Unit 9 is the cream of the crop. Direct Gulf Front, high-floor views make this one of the most spectacular luxury condo's on all of Anna Maria Island. What you get on the inside is no less outstanding. The deep cherry wood island style furniture is the finest around. Granite countertops,... View all property information
Make Inquiry
From
$200
Per Night
1 / 30
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (7) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Castnetter Beach Resort is located in the center of beautiful Anna Maria Island and directly across the street from the 7-Acre "Manatee Public Beach." Castnetter's has been a family favorite for Beach-Goers, Sun-Seekers, Boaters, Fishermen and Fun-Lovers alike since 1967. Extensive renovations... View all property information
Make Inquiry
5 of 5 stars Reviewed April 7, 2013
We just got back from a GREATweek on Anna Maria island and stayed in Castnetter #6 which is adjacent to and essentially identical to Castnetter 5. The 2 bedroom condo was...
See all reviews
From
$456
Per Night
1 / 27
Payment Protection
3 Bedrooms, 7 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
You'll be hard-pressed to find something more luxurious than this beautiful three bedroom, two-and-a-half bath unit at the prestigious La Casa Costiera. These high-end condominiums are in demand year-round...take one step inside and you'll immediately know why. You'll find all the luxury touches,... View all property information
Make Inquiry
From
$186
Per Night
1 / 16
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy your Anna Maria Island vacation in this marvelous three bedroom/two bath pool home just 300 yards to the beach! You'll feel instantly at home in this bright and cheery cottage designed with island living in mind. Tropical décor and an open floor plan are perfect accompaniments to beach... View all property information
Make Inquiry
From
$179
Per Night
1 / 9
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 12
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Authentic beach side house sleeps 12 comfortably, has spacious amenities with great outdoor spaces, and has quick access to the beach and trolley line. It's in a quiet area close to one of Florida's greatest stretches of beach! This house was built from two surplus WWII Army barracks in a quiet... View all property information
Make Inquiry
From
$186
Per Night
1 / 25
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
Make Inquiry
From
$1,995
Per Week
1 / 22
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (25) Make Inquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Escape to the Breakers, one of the finest luxury gulf front vacation homes on Anna Maria Island, located at 102 31st Street in Holmes Beach. Enjoy the tropical breezes and aqua-blue surf from the deck overlooking the white sand beach and sparkling Gulf of Mexico. Watch the dolphins cavort in the... View all property information
Make Inquiry
3 of 5 stars Reviewed August 24, 2014
Beach house is in a good location, right on beach and set off main Gulf Drive which can be noisy. Was somewhat dirty with moldy showers but I guess this is expected from a highly...
5 of 5 stars Reviewed July 6, 2014
This is a great little house. Well kept and well stocked. Only drawback is that it sets flush to the public access - parking in the side drive may result in your car getting...
See all reviews
From
$143
Per Night
1 / 15
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
About this property
Very comfortably furnished and updated home equipped with every vacation need. Washer and dryer,cable televisions, Wi-Fi, land line phone, screened rear porch for outdoor smoking only There is an outdoor gas grill.. Well-behaved dogs up to 25 pounds are permitted for extra fee of $100.00. All... View all property information
Make Inquiry
From
$200
Per Night
1 / 21
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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 and kitchen sleeps up to 6 to... View all property information
Make Inquiry
From
$200
Per Night
1 / 15
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
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 to 4. There are two double... View all property information
Make Inquiry
From
$90
Per Night
1 / 21
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
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 swimsuit and toothbrush. Condo... View all property information
Make Inquiry
From
$200
Per Night
1 / 17
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Island Paradise #3 3708 Gulf Drive Unit 3 Holmes Beach, Fl. 34217 Island Paradise is just that- the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any... View all property information
Make Inquiry
5 of 5 stars Reviewed August 17, 2014
The unit was very clean & well kept as well as the entire building. Our view of the Gulf of Mexico from the living room was breath taking. The pool was nice size and clean. We...
See all reviews
From
$120
Per Night
1 / 10
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This lovely property features a tropical setting surrounding a heated swimming pool. The six unit complex is located one block from the beach. Great for family reunions or wedding parties. This unit is a one bedroom one bath full size apartment. King bed in bedroom and a sofa sleeper in the... View all property information
Make Inquiry
From
$130
Per Night
1 / 26
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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 parking and outdoor deck with... View all property information
Make Inquiry
From
$130
Per Night
1 / 12
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
One bedroom two bath room full size apartment with separate bedroom has king size bed. Just steps to the beach. View all property information
Make Inquiry
From
$200
Per Night
1 / 23
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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 and kitchen sleeps up to 6 to... View all property information
Make Inquiry
From
$286
Per Night
1 / 49
6 Bedrooms, 4 Bathrooms, Sleeps 16
Details Reviews (2) Make Inquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
*** Ask about our specials through the end of the year!! *** The world-famous Old Florida charm of Anna Maria meets brand-new, modern living in Villa Chianti, our latest FABULOUS vacation rental. 6 Bedrooms, sleeps 14. Villa Chianti boasts one of the largest beach entry pools on the island with... View all property information
Make Inquiry
4 of 5 stars Reviewed October 2, 2012
This house was beautiful and only a short distance from the beach. We had a large extended family and everyone had plenty of room. The house was clean, but the walls need some new...
See all reviews
Go to map view
Book Online(93)
Use filters to find the best results!

Suitability

  • Wheelchair access (25)
  • Elder access (121)
  • Suitable for children (147)
  • Pet friendly (82)
  • Smoking allowed (1)

Amenities

  • Internet (351)
  • All pools (283)
  • Grill (278)
  • Other outdoor space (232)
  • Parking (217)
  • View all amenities
Filter search results by:
Book Online(93)

Suitability

  • Wheelchair access (25)
  • Elder access (121)
  • Suitable for children (147)
  • Pet friendly (82)
  • Smoking allowed (1)

Amenities

  • Internet (351)
  • All pools (283)
  • Grill (278)
  • Other outdoor space (232)
  • Parking (217)
  • View all amenities
Holmes Beach Vacation Rentals

Holmes Beach is a small town on Anna Maria Island in the Gulf of Mexico just south of Tampa Bay. It boasts miles of gorgeous white, sandy beaches, emerald Gulf waters, abundant sunshine, and an eclectic selection of vacation rentals. Visitors to Holmes Beach can stay anywhere from a luxurious beachfront house to a rustic rental cottage. Friendly locals welcome everyone to relax and enjoy this “Florida old charm” paradise.

Where to Stay in Holmes Beach

Rental homes can provide not only flexibility but the amenities of the best resorts at a fraction of the price. If you are vacationing with the family, having extra space to spread out is also an asset. Whether you want a weekend getaway or a long trip the rental choices are endless, and you’re sure to find something that will fit your family’s needs.

Fun things to do in Holmes Beach

A scooter is an inexpensive and fun way of getting around the island from your vacation rental. If you want to spend a day on the water, there is excellent fishing in the waters surrounding Anna Maria Island. Take a charter boat and head out in the Gulf for an exciting day of sport fishing. The grouper, snapper, or mackerel you catch can provide the ingredients for a delicious seafood dinner at your vacation rental. Inshore or backwater fishing is also very popular.

Enjoy a beach picnic with the locals under the Australian Pines, or find a secluded cove and enjoy some private sunbathing. Prefer an animated beach crowd? Then the all-you-can-eat pancake breakfasts at "Cafe on the Beach" is your scene.

More beach Fun

Join a volley ball game. There are numerous nets along the beach, and there is always an exciting game taking place. Not in for that much activity? Then lie on the beach soak up some sun while you cheer for your favorite team.

Dining and entertainment

Enjoy a burger and a cold beer at Dusty’s Tavern steps away from your vacation rental. The Beach House Restaurant provides beachfront dining and live music for your enjoyment. Enjoy fresh grouper and a beer close to your vacation rental. You can also rest and relax at the pool at your vacation rental and enjoy a barbeque with your family and friends. Whatever your choice, you will leave the island with unforgettable memories.