Holiday houses in Philadelphia

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Top-rated holiday rentals in Philadelphia

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Guest favourite
A charming villa with a spacious covered patio is surrounded by lush greenery. The garden features tropical plants and a seating area with dark-finished furniture. Large windows provide natural light to the interior, while the double-story structure is enhanced by wooden accents and palm trees.
Villa in Ocho Rios

Private Seafront Villa near Ochi

Located directly on the ocean and room for 7 -- bring the Fam! Stylish Villa with three bedroom plus sleeper-den with four full bathrooms offers Caribbean charm and modern sensibilities. Full kitchen, super-comfy living area fronts an expansive dining/bar and lounge area with views of the sea that go on forever. Included: Starlink Wifi, a 65" SmartTV and a/c throughout; your private housekeeper/cook is there to take care of your every need. Enjoy a unique, relaxing Jamaican vacation today!

4.94 out of 5 average rating, 83 reviews
Top Guest favourite
Home in Priory

Star Apple Getaway |Pool |Playground

Relax with the entire family at this peaceful, relaxing & modern getaway. Located in the well sought after gated community, The Crest in Richmond Estate, St Ann. Equipped with 24hr security & surveillance. The complex offers supermarket, private beach, infinity pool, lounge, gym, tennis court, basketball court, children’s playground , panoramic view of the Caribbean Sea & a tranquil space. This house is well suited for up to 8 guests. This listing has outdoor cameras monitoring the premises.

4.98 out of 5 average rating, 102 reviews
Guest favourite
Home in Browns Town

Swing Bed in the Hills: Secure Escape, Fast wifi

Tucked away in the cool hills above Browns Town, this bright villa blends indoor comfort with outdoor serenity. Our signature screened gazebo with swing bed is made for reading, napping, or stargazing; no bugs, just breeze. Inside: 2 king bedrooms, 2.5 baths, full kitchen, 75" TV, dedicated office, and fast Wi-Fi (136 Mbps). Outside: gated parking, local shops steps away, beaches 15 minutes away. Perfect for couples, families, or remote workers craving peace, privacy, and genuine Jamaica. 🇯🇲

4.85 out of 5 average rating, 47 reviews
Top Guest favourite
Home in Runaway Bay

ElizabetShanaya at the Savannah Vistas

Enjoy a stylish experience at this centrally located home away from home. Discover ElizabetShanaya at The Savannah Vistas, nestled along St. Ann’s pristine coastline in Runaway Bay. This lovely home blends comfort and relaxation with authentic island beauty. Offering a magnificent view overlooking the sea, with ocean breezes, and warmth. Whether you're unwinding at the shaded frontyard patio or lounging by the nearby pool, or simply soaking in the serenity, this is your escape in paradise.

5.0 out of 5 average rating, 16 reviews
Guest favourite
A spacious bathroom features a large black Jacuzzi positioned on a multi-step platform, surrounded by glossy black and white tiles. Natural light filters through an arched window dressed in bright yellow curtains. A standing shower is visible, along with a sink and elegant wall-mounted mirror.
Home in Runaway Bay

Cambridge mi casa ur casa w/pool & beach access

We offer newly- renovated comfortable two- floor apts in a friendly safe community overlooking CARDIFF HALL Beach in the Resort Town of Runaway Bay in St. Ann Jamaica ▪️No need to worry about security / safety because there are 24 hour surveillance camera and host lives on property ▪️We offer one 1bdr & 2br ▪️Price starts from 100US for 2 guests and increases by 30US per additional guests ▪️We are about 1hr away from the Sangsters International Airport ✈️ 25 mins from Ocho Rios

4.93 out of 5 average rating, 186 reviews
Superhost
A shaded gazebo offers comfortable seating surrounded by lush greenery. Palm trees and vibrant foliage frame a view of the expansive lawn leading to the beach. The sea glimmers in the distance under a clear blue sky, creating a serene outdoor retreat.
Bungalow in Saint Ann

Kling Kling Beach House

Kling Kling is a beach house with a family feel, set within a large lawn running down to an almost fully private beach, a river for freshwater swimming, a reef for snorkelling, a fantastic housekeeper cook and a one of a kind man about the place. Just mins drive to shops or tourist facilities. Nearby scuba facilities, waterfalls, water parks, markets, tennis , golf, riding, the list goes on, both mainstream and off piste local. For more pics follow our Instagram: klingklingbeachhouse.

4.87 out of 5 average rating, 213 reviews
Top Guest favourite
Condo in Ocho Rios

Salt & Breeze Villa - Apartment in Ocho Rios

Come relax in a clean & stylish space with a tropical vibe. Located in Ocho Rios, Jamaica, you're minutes away from popular attractions including Dunn's River Falls, Mystic Mountain, Dolphin Cove & Green Grotto Caves, with easy access to both ends of the island. The property sits within a secure gated community, offering beach access and an infinity pool, plus great dining nearby at Plantation Smokehouse, Juici Patties, Sharkies & Uncorked. Airport pickup available on request.

5.0 out of 5 average rating, 28 reviews
Top Guest favourite
A charming outdoor deck features several light blue bar stools, arranged around a raised bar area with an umbrella for shade. The wooden structure of the cabin is visible in the background, surrounded by lush greenery and a clear sky.
Cabin in Runaway Bay

A/C cabin outdoor jacuzzi, access to private beach

Take a visit to the historical city of Runaway Bay, St. Ann. Stay at the Cozy Cabin and experience a piece of this historical city. The cabin is nestled in the cool hills of Runaway bay. It is yet, conveniently located just 5 - 10 minutes drive from world renowned restaurants and excursion experiences. Kick back and relax in comfort and style. Get the best of both worlds: the magical Runaway Bay mountains and the beautiful Caribbean sea. A vacation you will never forget!

4.96 out of 5 average rating, 123 reviews
Guest favourite
Home in Runaway Bay

Olive Breeze II

Enjoy an unforgettable stay in our warm and inviting studio, thoughtfully designed to provide the perfect blend of comfort and style. Whether you’re here for a relaxing getaway or a work related visit, this space offers the ideal atmosphere to unwind and feel at ease. Set in a safe and strategically located area, you’ll find have a variety of restaurants, convenience stores and attractions. You will find yourself surrounded by peace, privacy and a sense of home.

5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Plantation Village

NEW~ Pool Access 3BR •Gated • Walk to the Beach

Welcome to your island getaway where laid-back coastal living meets modern comfort. This spacious 3-bedroom, 3.5-bath vacation home is perfectly designed for you with a quick stroll to the onsite private beach ✨ Why You’ll Love This Home ✔︎ Private beach access ✔︎ Secure gated community with 24/7 security ✔︎ Pool access ✔︎ Spacious, modern design ✔︎ Seamless self check-in via keypad ✔︎ Free on-site parking ✔︎ Fully air-conditioned

4.86 out of 5 average rating, 22 reviews
Superhost
Villa in Runaway Bay

Sea Vista Escape | Pool | Hot Tub | Gated | For 12

Welcome to Sea Vista Escape. A luxury villa in the Greater Ocho Rios. Perfect for families, friends, reunions, birthdays, anniversaries, bachelor/bachelorette trips, and special events. • Ocean views • Hot tub • Game room • Fast Wi-Fi • Gated community • Private chef & catering available • Airport transfers & celebration packages

5.0 out of 5 average rating, 3 reviews
Superhost
Villa in Ocho Rios

Las Olas Villa 4BR Pool, Chef, Ocho Rios

Escape to Las Olas Villa, a private four-bedroom retreat near Ocho Rios with pool, basketball court and four ensuite king bedrooms. Our concierge team arranges everything from private chef to yacht charters, in-villa massages, and airport transfers, excursions and more! Arrive, unwind, and let Jamaica come to you.

5.0 out of 5 average rating, 7 reviews

Popular amenities for Philadelphia holiday rentals