House holiday rentals in Caribbean

Rincón Sea Beach Cottage w/Pool, Steps to Beach!

This unique beach house w/pool, is in the quaint, desirable beach community of Sea Beach Colony, in the heart of Rincon. Only 5 houses from the beach, with ocean views, walking distance to all. Filled with art, & lovely furnishings, this tropical home offers the experience of Caribbean coastal life. Sleeps 5 total / 2 bdrm/1.5 bth in Main house, Casita -1 full w/full bath for guests. The outdoor kitchen, dining & living room are magazine worthy & there is even an outdoor soaking tub. WIFI & AC

Family Getaway | Private Pool | Entertainment

Welcome Home Nestled in a safe, family-oriented neighborhood, our spacious home offers a peaceful getaway for all guests. Family-Friendly: Saltwater pool and game room. Comfortable and Relaxing: Spacious, clean, and cozy. Outdoor areas for sunbathing and fireplace evenings. Explore with Ease: Walk-friendly area near stores and restaurants. Bikes available. Amenities Galore: BBQ grill, outdoor fireplace, and more. Seamless Experience: Great communication, smooth check-in, and check-out.

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, 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!

Welcome to Paradise at CollinsCoveCaptiva!

Welcome to your dream getaway in this beautifully updated, turnkey Key West-style home located in the heart of Captiva Island within walking distance to the village. Nestled in the charming Sunset Captiva community—lined with brick-paver streets—this home offers direct access to award-winning beaches and a private marina on the Bay. Boater’s Paradise? Immediate availability for the brand-new HOA-maintained boat docks. Or spend your days relaxing in the oversized, heated resort-style pool.

STUNNING Canal Ranch Walk to the Tigertail Beach

NEW LISTING! Newly Remodeled 4 Bed, 2 Bath that sits in a very exclusive location less than 2 blocks from Tigertail Beach! Our vacation home offers an abundance of updated space! Plenty of outdoor entertaining within the large enclosed pool area. Enjoy the several "extras" to use during your stay including, bikes, beach chairs, coolers, and much more! You won't find a better value for your family and be able to walk to the beach! Please note: TV in every room set up for streaming ONLY

❤ 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.

Yellow Home Free Pontoon Rental! See details

If you book your stay for the days shown below May 10th - May 23rd, 2025 May 26th - June 7th, 2025 July 5th - July 26th, 2025 Receive a free 2 day boat rental for a week reservation, 1 day for a 3 days or more reservation. Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home nestled off of US 1. Kayaks included with the rental. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

Cottage between Sanibel and Edison / Ford Estate

This is the ultimate getaway for our guests. Yes…. you’re going to have an entire house for yourself . Feel free to enjoy 2 bedroom / 2 bathroom house with a Florida room, plus outside patio with gazebo(BBQ) and large back yard. Our newly renovated retreat is in the perfect location that is close to the beach, near all the best restaurants, and has all the amenities you will need for a breezy family vacation. Cleaning fee only $49!

Beachfront home with private access, walk to town!

Welcome to your own private getaway directly on Siesta Beach! Meticulous, updated unit with amazing location to the village and access to tow You will literally, walk out your door, down the steps, and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedroom 3 bathroom beachfront home with Gulf views that sleeps 8.