Holmes Beach beach vacation rentals

4.77 out of 5 average rating, 104 reviews

A bright studio apartment features a spacious bed dressed in light grey linens. Two bedside lamps provide soft illumination. A small kitchenette is visible, while a doorway leads to a bathroom with modern fixtures. Natural light enters through a door leading to the private patio.

Apartment in Siesta Key

Gertrude's Siesta | Patio & 1-min to Beach/Village

The Village Studio Top location on island! Apartment with full kitchen, private patio, gated courtyard, in world famous Siesta Village! Leave the car behind and walk to white-sand beaches, 20 bars and restaurants, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Experience a combination of fun ease and relaxation you can't get in other vacations! Book a special getaway now! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta

4.88 out of 5 average rating, 153 reviews

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

Home in Indian Rocks Beach

The image showcases a serene beach scene with soft white sand in the foreground, gently lapping waves in a range of turquoise and green hues, under a clear blue sky featuring wispy clouds. The tranquil waters stretch to the horizon.

4.99 out of 5 average rating, 167 reviews

Luxe BeachHouseA Heated Pool, 2 min walk to Beach

Welcome to your home away from home. Sand,sun and ocean breeze are waiting for you. Our modern Beach House is located 2 minutes walk from the beautiful and quite beach with direct beach access.Its a newly built three story house with nice backyard,heated pool,hot tub and beautiful rooftop. We have everything that you need for bigger groups of families to relax on your Beach vacation.Our Beach House is in a quite neighborhood and still walking distance from restaurants,bars and stor. BTR#2099

A covered porch area features comfortable seating surrounding a low table, with a view of a heated pool. String lights create a soft illumination along the ceiling, while lush greenery surrounds the outdoor space, enhancing the tranquil atmosphere.

4.96 out of 5 average rating, 122 reviews

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

4.92 out of 5 average rating, 294 reviews

❤ Villa & Garden in Downtown ~ 5 Min to Beaches

Our bright and contemporary Heart Villa offers the quintessential Sarasota downtown and beach experience. It is nestled among tropical trees in a charming cul-de-sac in historic Laurel Park – right in the heart of downtown with loads of restaurants, boutiques, and sights on offer. Several fantastic beaches are just 5-mins ride away! And the villa's private garden is the perfect place to enjoy alfresco dining! We’ve poured our hearts & souls into this villa, it's our family business.

An outdoor space features a modern tabletop air hockey game and a classic skee-ball machine, inviting friendly competition. The area is surrounded by a lush green garden, with wooden fencing providing privacy, while natural light streams in through screened windows.

4.95 out of 5 average rating, 19 reviews

Warm, Luxury Oasis in Central Sarasota

Choose to stay at a home which has it all. Professionally designed and hosted by a 10-year SuperHost, this property offers incredible value. Superbly comfortable beds and linens, SUPER FAST internet, thoughtful furnishings, tons of activities & games, fully equipped for babies and toddler needs, extremely central location, large, high-end TVs, a jacuzzi, 2-person hammock, in-ground fire pit…. And fur babies welcome… you name it, this home has it. Welcome to Sarasota Paradise.

A spacious living area features a light gray sofa arranged around a dark coffee table, with a neutral area rug underneath. A flat-screen television is mounted on the wall, and large windows allow natural light to illuminate the space, creating a welcoming environment.

4.98 out of 5 average rating, 390 reviews

The Cottage at Central Park II

If you are looking for the perfect family home to cater to your every need, then look no further! With plenty of space to spread out, natural light that pours into every room, an expansive and private fenced in yard, screened-in porch and outfitted kitchen- this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

Apartment in St. Pete Beach

A tidy outdoor area features charming green accents with a bright door leading to a unit. String lights create a soft illumination above a pathway lined with white stones and lush greenery, while a small table and chairs invite relaxation in the pleasant Florida climate.

4.8 out of 5 average rating, 311 reviews

Cactus-Themed Retreat,Walk to Beach<1 mile: 4plex

🌵Fiesta Siesta – Where Every Day Feels Like a Party!🌴 Feed me tacos and tell me I’m pretty—because life’s too short for anything less! Welcome to Fiesta Siesta, a fun, vibrant escape just steps from Upham Beach in sunny St. Pete Beach. One of four uniquely themed units in a gated complex, this playful retreat is decked out in a vibey cactus theme that’s all about fiesta and siesta—because, why choose? Book now and let the fiesta begin! 🎉🌮

4.82 out of 5 average rating, 135 reviews

Two wooden beach chairs are placed under a large blue striped umbrella, with a cooler positioned between them. The serene turquoise waters and sandy beach create a relaxing coastal scene, with gentle waves lapping at the shore.

Home in Bradenton Beach

50 Steps to Beach Villa Hot Tub 1bd modern cottage

Luxury Beach Cottage w/ HOT TUB, Fire Pit & BBQ. 1 bed/1bath sleeps 4 This is your chance to enjoy a unique getaway on the nicest beach! Stay in our newly remodeled beach cottage. White sandy beach & turquoise water is literally 50 ft from the door. Everything you need for a delightful & relaxing day at the beach is included. Chairs, beach towels, umbrella,. Enjoy the convenience of this premium location across Gulf blvd to Beach.

4.98 out of 5 average rating, 238 reviews

A serene beachscape is captured under a clear blue sky, featuring soft white sands that lead to gentle waves. The water transitions from light turquoise to deep blue. A few figures can be seen enjoying the shoreline in the distance, enhancing the peaceful atmosphere.

Apartment in Dunedin

My Favorite Place 🍊downtown & city approved

LEGAL, CITY APPROVED 1 bedroom apartment w full kitchen, living , dining & separate bedroom located on the red brick streets of downtown Dunedin. Private entrance. BIKES Super clean Private driveway free parking Two great bikes Great for couples Tastefully decorated. Comfortable Queen bed. Luxurious bedding. Super clean. Shampoo, conditioner, body wash, coffee, tea, drinking water provided. SUPER CLEAN No pets

Cottage in Indian Rocks Beach

A view of the beach is captured from a balcony, showcasing vibrant turquoise waters and a sandy shore. Sunbathers and colorful umbrellas dot the beach, while charming coastal cottages frame the scene. The image conveys a relaxed atmosphere, with soft ocean waves visible in the background.

5 out of 5 average rating, 42 reviews

Upper Deck prime area no condos/crowds

The location is one of the best on the West Coast. I’ve had only 5 stars from my guests. Our places are fully stocked and very clean. This whole property is award winning! Plus, we attract artists -Also our cottages have appeared on many calendars, cards and artists' canvas.

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Popular amenities for Holmes Beach vacation rentals

Laptop-friendly workspace

Stay near Holmes Beach's top sights

Anna Maria Island278 locals recommend

Ana Maria Island Beach14 locals recommend

Holmes Beach11 locals recommend

Anna Maria Island Chamber374 locals recommend

The Sandbar Restaurant168 locals recommend

The Waterfront Restaurant99 locals recommend

Vacation rentals in Holmes Beach

4.93 out of 5 average rating, 27 reviews

A tranquil beach scene features clear turquoise waters with gentle waves lapping the shore. Several individuals are seen swimming and enjoying the water, while the sandy beach stretches under a blue sky dotted with soft clouds. Sparse greenery lines the beach in the background.

Home in Nokomis

Last minute May ,house 2 Mil beach .Pets welcome

4.83 out of 5 average rating, 12 reviews

A spacious living and dining area features a modern sectional sofa contrasting against light wood flooring. A large flat-screen television is mounted on the wall, and a dining table with multiple chairs is visible in the background. Soft lighting enhances the open layout.

Home in Largo

Brand new home, Modern design, Close to Beaches

Townhouse in Holmes Beach

An aerial view captures a beachside community with white homes nestled among palm trees. The coastline and ocean are visible in the background, while nearby buildings and roadways provide context for the location. The neatly arranged rooftops highlight the peaceful neighborhood ambiance.

4.99 out of 5 average rating, 137 reviews

Summer Discounts Available! Steps from the Beach!

4.93 out of 5 average rating, 60 reviews

An aerial view showcases a spacious property featuring a heated private pool and a vibrant pickleball court. A serene pond is visible in the background, surrounded by greenery. The layout includes well-maintained outdoor spaces and convenient access to the home.

Home in Bradenton

Pickleball! Pond! Private Heated Pool! Foosball

A spacious bedroom features a elegant white bedframe with a black-and-white patterned comforter. A lamp sits on a nightstand beside the bed. A ceiling fan is visible above, and natural light enters through a window with multiple panes.

5 out of 5 average rating, 3 reviews

Walk to the beach.

Hotel room in Clearwater Beach

A dock area is visible over calm waters, featuring a wooden table surrounded by four black woven chairs. Buildings and palm trees can be seen in the background, creating a relaxed waterfront atmosphere.

4.72 out of 5 average rating, 240 reviews

Bay Apartment 3

5 out of 5 average rating, 3 reviews

Home in Siesta Key

Rustic Sands - 650

4.86 out of 5 average rating, 145 reviews

A tranquil lagoon-style pool is surrounded by lush tropical landscaping. Soft lighting enhances the evening atmosphere. A staircase leads to a second-level balcony, while shaded lounges offer a relaxing spot near the water's edge, creating a serene environment for guests.

Townhouse in Siesta Key

"Relax Here" -Royal Palm Suite- Siesta Key Beach

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Other great vacation rentals in Holmes Beach

4.97 out of 5 average rating, 31 reviews

The exterior of the home features a spacious driveway leading to a two-story structure with a charming balcony. Lush greenery and manicured landscaping enhance the inviting curb appeal, complemented by soft sunset colors illuminating the sky.

Home in Palma Ceia

SouthTampa-Family&Group Oasis-3K bd, private pool

Apartment in Indian Rocks Beach

4.8 out of 5 average rating, 273 reviews

Enjoy brand new vacation 2/2 condo & water park!

4.89 out of 5 average rating, 9 reviews

Home in Tampa

Bring your family and friends to our luxury airbnb

4.91 out of 5 average rating, 173 reviews

A well-maintained staircase with beige carpeting is pictured, featuring white wooden railings and spindles. The walls are painted in a neutral tone, and a small wall-mounted shelf is visible beside the stairs, enhancing the clean design.

Condo in Redington Beach

2min walk to the beach/pool, BBQ/great area, RO110

4.89 out of 5 average rating, 103 reviews

Home in Tampa

Luxury Home centrally located in Tampa Bay!

5 out of 5 average rating, 6 reviews

Home in Bradenton

Luxury ~ Heated Pool ~ Games ~ near AMI, IMG, SRQ

5 out of 5 average rating, 26 reviews

Condo in Indian Shores

Amazing views & steps to beach 2B-2Bath-Pool 333