Location

Dates

Guests

Vacation rentals in Holmes Beach, Florida, United States

[Living area] Smart TV with Netflix & sofa bed

[Dining area] Free bikes, kayaks & beach gear are included in this rental!

[Kitchen] Fully stocked & equipped kitchen with updated appliances. Coffee maker & complimentary coffee provided.

[Living area] Smart TV with Netflix & sofa bed

Here's one of my 5-star reviews...improving every day!

Walk score 82 | bikes | kayak | 214mbps | foam bed

1 bedroom·1 bath

St. Petersburg • Florida

$ 496,00 USD totaal voor 3 nachten

24–27 okt 2026

Entrance to Sunray

patio outside private to Sunray

The SunRay Tiny House

XLTwin bed with nested twin below

XLTwin bed with nested twin below

The SunRay Tiny House

1 bedroom·1 bath

St. Petersburg • Florida

4(6 reviews)

$ 246,42 USD totaal voor 3 nachten

1–4 nov 2026

The tiny home sits on a private 1.5 acre inland peninsula!

[Patio] Shared outdoor living space with fire pit

[Living area] This luxury 270sqft craftsman style tiny home is in the ideal location for your beach getaway.

Outdoor dining options available in the screened in lounge.

[Kitchen] Fully equipped kitchen featuring stainless steel appliances & gas cooktop. Coffee maker for all the coffee lovers out there!

·@Tiffanythetinyhome| island | netflix|bike|hammock

1 bedroom·1 bath

Sarasota • Florida

$ 449,00 USD totaal voor 3 nachten

24–27 okt 2026

[Living area] Smart TV with Netflix & Hulu

Waterfront tiny home sits on a private 1.5 acre inland peninsula! The perfect location for bird watching & kayaking around the lake.

[Living area] Doorway to the left leads into the main bedroom.

[Kitchen] Fully stocked & equipped kitchen with large farm sink and convection cooktop.

[Living area] French doors open up into the spacious backyard. Sofa converts into a bed for additional sleeping space.

@Shellmateisland |tiny home| island| bikes| kayaks

1 bedroom·1 bath

Sarasota • Florida

$ 571,00 USD totaal voor 3 nachten

24–27 okt 2026

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

7 bedrooms·7 baths

Madeira Beach • Florida

$ 5.555,08 USD totaal voor 3 nachten

24–27 okt 2026

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

2 bedrooms·2 baths

Madeira Beach • Florida

$ 1.865,94 USD totaal voor 3 nachten

24–27 okt 2026

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath

Madeira Beach • Florida

$ 1.669,59 USD totaal voor 3 nachten

24–27 okt 2026

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath

Madeira Beach • Florida

$ 1.568,57 USD totaal voor 3 nachten

24–27 okt 2026

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

1 bedroom·1 bath

Madeira Beach • Florida

$ 1.516,36 USD totaal voor 3 nachten

24–27 okt 2026

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

1 bedroom·1 bath

Madeira Beach • Florida

$ 1.568,57 USD totaal voor 3 nachten

24–27 okt 2026

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

Park & Pool Across the Street and 9 Mins to Beach

4 bedrooms·2 baths

St. Petersburg • Florida

4.95(43 reviews)

$ 1.482,00 USD totaal voor 7 nachten

24–31 okt 2026

Spotless & Tranquil Bungalow (Allergen Friendly)

Ra the Tortoise, he loves cucumbers so bring some snackies!

Spotless & Tranquil Bungalow (Allergen Friendly)

Spotless & Tranquil Bungalow (Allergen Friendly)

Spotless & Tranquil Bungalow (Allergen Friendly)

Spotless & Tranquil Bungalow (Allergen Friendly)

1 bedroom·1 bath

Parrish • Florida

5(82 reviews)

$ 718,80 USD totaal voor 3 nachten

1–4 mrt 2027

Comfortable sleeper sofa for guests while immersed in the tranquil ocean vibe!

Wonderful open space living area to relax and watch your favorite game or a good movie!

Have a picnic right on the water with the breathtaking view!

Enjoy your morning coffee and breakfast at the open concept dining area.

The bay beach in the community is a day of fun and sun!

Bahia Beach Calm Ruskin Retreat

2 bedrooms·1½ baths

Ruskin • Florida

$ 637,75 USD totaal voor 3 nachten

24–27 okt 2026

Comfortable sleeper sofa for guests while immersed in the tranquil ocean vibe!

Wonderful open space living area to relax and watch your favorite game or a good movie!

Enjoy your favorite movie or watch your favorite team on this nice smart TV and relax!

Enjoy your morning coffee and breakfast at the open concept dining area.

Breathtaking views off the living area!

Bahia Beach Calm Ruskin Retreat

2 bedrooms·1½ baths

Ruskin • Florida

$ 586,25 USD totaal voor 3 nachten

3–6 nov 2026

Private screened pool with lounge chairs and easy indoor-outdoor access

Primary bedroom — king bed with coastal luxury bedding, wall-mounted smart TV, and direct sliding glass door access to the private screened pool.

Coastal dining room at Sun Oasis — a farmhouse-style table set for six with blue place settings and teal glassware, teal front door visible beyond, flowing into the living room.

Full living room — two plush sofas, striped armchair, coastal round ottoman, oversized Oasis on 40th turtle 70-inch TV art, guest book on the coffee table, and the game room archway beyond.

Screened private pool with string lights for relaxing evening swims

Sun Oasis Heated Pool Game Room and Wood Fire Pit Near St Pete Beaches

3 bedrooms·2 baths

St. Petersburg • Florida

5(72 reviews)

$ 703,97 USD totaal voor 3 nachten

25–28 okt 2026

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

1 bedroom·1 bath

Madeira Beach • Florida

$ 607,00 USD totaal voor 3 nachten

24–27 okt 2026

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

1 bedroom·1 bath

Madeira Beach • Florida

$ 607,00 USD totaal voor 3 nachten

24–27 okt 2026

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 1

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 2

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 4

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 5

1 Bedroom Apartment/ Pets friendly/ 15 mins DTSP image 6

1Bedroom/ 10 mins to Downtown Saint Peterburg

1 bedroom·1 bath

St. Petersburg • Florida

4.36(25 reviews)

$85 – $95/ nacht(excl. kosten & belastingen)

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

0 bedrooms·1 bath

St. Petersburg • Florida

4.32(19 reviews)

$ 316,00 USD totaal voor 3 nachten

24–27 okt 2026

Beautiful Sarasota villa in a quiet tropical setting with a screened lanai for comfortable outdoor living. Surrounded by palm trees and lush landscaping, this peaceful retreat offers privacy and relaxation just minutes from beaches and attractions.

Sarasota Villa with Pool Access Tennis Near Beach image 2

Sarasota Villa with Pool Access Tennis Near Beach image 3

Sarasota Villa with Pool Access Tennis Near Beach image 4

Sarasota Villa with Pool Access Tennis Near Beach image 5

Sarasota Villa with Pool Access Tennis Near Beach

2 bedrooms·2 baths

Sarasota • Florida

5(5 reviews)

$ 1.543,58 USD totaal voor 7 nachten

24–31 okt 2026

Magnolia near the beach and downtown St. Pete image 1

Magnolia near the beach and downtown St. Pete image 2

Magnolia near the beach and downtown St. Pete image 3

Magnolia near the beach and downtown St. Pete image 4

Magnolia near the beach and downtown St. Pete image 5

Magnolia near the beach and downtown St. Pete

5 bedrooms·3 baths

St. Petersburg • Florida

4.85(150 reviews)

$ 773,23 USD totaal voor 3 nachten

26–29 okt 2026

Property grounds

Private kitchen

Beachfront Condo at La Contessa!, 3BD/3BA, Poolside Cabana, Private Fishing Pier

3 bedrooms·3 baths

Redington Beach • Florida

5(12 reviews)

$ 11.215,25 USD totaal voor 30 nachten

15 nov – 15 dec 2026

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

Florida Beachside Home

2 bedrooms·2 baths

Walton County • Florida

5(12 reviews)

$ 739,50 USD totaal voor 3 nachten

24–27 okt 2026

Casa Noir by Perez Benitez image 1

Casa Noir by Perez Benitez image 2

Casa Noir by Perez Benitez image 3

Casa Noir by Perez Benitez image 4

Casa Noir by Perez Benitez image 5

Casa Noir by Perez Benitez

4 bedrooms·2 baths

St. Petersburg • Florida

5(6 reviews)

$300/ nacht(excl. kosten & belastingen)