Holiday rentals with a kayak in Caribbean

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Cayo Loco Villa 2 Deserted PinkSand Beach 2 Adults

S2E2 NETFLIX "WORLD'S MOST AMAZING VACATION RENTALS"! Beachfront villa right on deserted secluded pink sand beach! Watch dolphins with your coffee/coconut water/tarts! Beach toys included! Eleuthera means 'freedom'! Tranquil authentic tropical island paradise fusing eco design w/comfort! 1 of 2 brightly colored villas! Beach stroll to dining/bar/pool! Fish/surf/boat/dive/kayak/paddle board/relax! Unspoiled pristine oasis! 1 bed 1-1/2 bath 2 ADULTS ONLY! NO SMOKING/KIDS/LOUD MUSIC/VISITORS/FIRES!

Adorable Boho-Style Beach Villa

This adorable studio apartment has been fully renovated & has everything you need to enjoy the perfect Caribbean getaway. Calypso Cove is directly across from the famous Seven Mile Beach, where you can swim in the crystal clear blue sea every day. The studio has a balcony so you can enjoy the sunset or a morning coffee. Walking distance to supermarket, restaurants, bank and pharmacy, this apartment is in the perfect location. Keurig coffee machine, deck chairs, fins and mask and beach umbrella.

Rum Cove on the Bioluminescent Bay with Ocean View

Welcome to Rum Cove – your private escape on the bioluminescent bay, just steps from the world-famous Rum Point. This bright & breezy 1-bedroom retreat is part of a charming triplex and offers stunning 360° views. Whether you’re relaxing on the patio, kayaking under the stars, or sipping coffee at sunrise, Rum Cove surrounds you with natural beauty & peace. A perfect space for couples, solo travelers or small families looking for a quiet getaway with the best of Cayman Kai on your doorstep.

Villa Arena - Beach Front

Villa Arena is a spacious oceanfront getaway designed for families and groups looking to relax in total privacy. With a newly built climatized pool, direct access to the sea, and a sandy beach just steps away, it offers the perfect blend of comfort and Caribbean charm. Enjoy family-style meals with optional chef service, daily housekeeping, and excursions like Cayo Arena, ATVs, and catamaran tours — all departing from your doorstep. Unwind, recharge, and make lasting memories at Villa Arena.

Tropical Modern Loft | SoHo Style | Concierge

Single night bookings welcome! A luxe art loft experience in the heart of St. Thomas, this exclusive space in a convenient central location provides a chic home base, with sleek design, concierge options, + creative vibes. Perfect for both adventure and serenity. Ample space to lounge, with a balanced historic/contemporary aesthetic, and near beaches, restaurants, historic landmarks, boutiques, + ferry/airport/transportation. Private gated parking and a cafe and art gallery right downstairs.

Villa Soreli - 1 B/R Oceanfront w/Pool

Villa Soreli, a bespoke Ocean Front Luxury Villa rental in Rainbow Bay, Eleuthera Bahamas. This 1 B/R private villa includes a Queen-sized Master bedroom with an additional Sleeper Sofa to accommodate a family of 4- ie. two adults & 2 children. Our villa is fully equipped with a full kitchen, indoor & outdoor shower, high end finishes & a plunge pool overlooking the Caribbean Sea. It is walking distance to Rainbow Bay Beach. Nestled in between the Caribbean Sea and the Atlantic Ocean.

Sailfish Villa Beachfront Magens Bay St. Thomas!

Private beachfront villa on world-famous Magens Bay Beach! Sailfish Villa is a 5BR/4.5BA oceanfront property with direct beach access. This listing features a 1BR/1BA beachfront cottage that sleeps up to 4 guests. Enjoy swimming with sea turtles, snorkeling, and kayaking just steps below the villa. Amenities include an outdoor shower, clear kayak, paddle boards, and stairs to the water. Located in the private neighborhood of Peterborg, just a short shoreline stroll to Magens Bay Beach.

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Villa DelEvan 4B / 1-bedroom villa

Centrally located on the Grace Bay Beach, a perfect place for luxury, rest & tasting the best island cuisine. Close to everything you need for a great vacation: Walking dist. from 4 restaurants - Mango Reef, Shark Bite, Baci & Simone’s. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated property, private parking, 24hr security. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.