Holiday rentals in Philadelphia

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Top-rated holiday rentals in Philadelphia

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
The exterior of a modern two-story building is showcased, featuring a combination of light and dark materials. Lush greenery surrounds the property, and a driveway leads to a garage. Large windows provide ample natural light, while balconies add to the contemporary aesthetic.
Home in Plantation Village
5 out of 5 average rating, 10 reviews

Elite Escape @ Paradisiac (near Ocho Rios)

Escape to paradise in this stylish & fun 3-bedroom, 3.5-bath beachside retreat near Ocho Rios! Perfect for families, this spacious home combines modern design & tropical charm. Enjoy bright, airy interiors, comfortable beds, and an open living space ideal for creating memories. With a view of the Caribbean Sea, you’ll find relaxation and adventure at your doorstep. Whether you’re soaking up the sun, exploring local attractions, or simply unwinding, this family-friendly getaway is yours to enjoy!

Guest favourite
The villa's exterior is showcased with a well-maintained façade, featuring decorative arches above large windows. The front entrance is framed by double doors. A paved driveway leads to a garage, with tropical plants lining the pathway and a backdrop of rolling hills under a clear blue sky.
Villa in Runaway Bay
4.83 out of 5 average rating, 47 reviews

Lakeside Villa • Spacious Villa Near the Beach

Welcome to this beautiful cosy villa, located in a quiet neighbourhood of Runaway Bay, featuring 3 bedrooms and 2 bathrooms. There is 24 hour security in the gated community. We're located 1 hour from Kingston, 45 min from Montego Bay and 15 min from Ocho Rios which includes many tourist attractions such as Dunn's River Falls, Dolphin Cove, Mystic Mountain, Chukka Cove, River rafting and Ocho Rios shopping complex. Enjoy a relaxed environment with sea breeze and a mountain view. Contact us!

Guest favourite
Home in Browns Town
4.85 out of 5 average rating, 46 reviews

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. 🇯🇲

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
4.94 out of 5 average rating, 160 reviews

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

Guest favourite
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 Laughlands District
4.88 out of 5 average rating, 206 reviews

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.

Superhost
The two-story villa is shown at dusk, with warm light glowing from the large open spaces inside. Comfortable lounge chairs line the stone pathway, leading to a spacious garden. Lush greenery surrounds the villa, creating a serene outdoor environment.
Villa in St Ann
4.71 out of 5 average rating, 7 reviews

Luxury Oceanfront villa, Tallawah#6 at Chukka Cove

Escape to Paradise at TALLAWAH, Villa 6 Unwind in this stylish two-bedroom villa on Jamaica’s north coast, tucked away in the exclusive Chukka Cove. Sweeping views of the Caribbean Sea and sunsets to match. Enjoy an open-concept living space with French doors, open to lush garden and seaside patio, perfect place to relax and recharge. Peaceful, romantic, unforgettable! Brings the magic of Jamaica to your doorstep. Come. Relax. Unwind. Experience the magic of Tallawah Villa 6.

Top guest favourite
Home in Saint Ann's Bay
5 out of 5 average rating, 42 reviews

Drax Hall Villa, Private Beach, 5-Star Hosting

15 min to downtown Ocho Rios. 11 min to Dunn’s River Falls, Mystic Mountain and Dolphin Cove. Walking distance to Starbucks, KFC, Pizza Hut & supermarket. Complimentary access to private beach: The Cove, which is a 15 min walk/ 3 min drive. Secure gated community: - shared pool - tennis court - 24-hr security A peaceful, low key atmosphere, suitable for families + professionals. NO PARTIES. Need more room? Ask about our sister property.

Guest favourite
Flat in Salem
5 out of 5 average rating, 14 reviews

Beachside Bliss at Paradisiac Beach Club

Welcome to your coastal escape at the exclusive ‎Paradisiac Beach Club where luxury meets laid back island charm our beachside retreat offers the perfect blend of comfort and style, just moments from pristine white sands and turquoise Waters. whether you’re looking to sip cocktail at sunset, unwind in the serene seaside setting or explore vibrant, local culture this is the ideal base for your dream getaway.

Superhost
Home in Runaway Bay
4.9 out of 5 average rating, 10 reviews

Gated Runaway Bay Townhome w/ Pool Near Beach

Welcome to this modern 2-bedroom, 2.5-bath townhome in Runaway Bay, Jamaica. Located in a secure gated community with 24-hour security and a shared pool, the home is just 5 minutes from the beach. Both bedrooms feature private balconies, and all rooms are air-conditioned with TVs. Perfect for couples, families, or friends seeking comfort, privacy, and easy access to beaches and attractions

Guest favourite
Home in Discovery Bay
4.88 out of 5 average rating, 16 reviews

Chillin in D’Bay

Come Chillin’ in D’Bay — Your Home Away From Home 🇯🇲 Stay in our cozy, modern tropical home in Discover Bay, St. Ann. 2 bedrooms • 2 bathrooms • Ocean view • Gated community Just 5 minutes from the beach, with outdoor dining, laundry, and all the comforts you need — budget-friendly and full of island vibes. Relax, explore, and enjoy Jamaica — come chill with us in D’Bay! 🌴

Guest favourite
Villa in St. Ann Parish
4.84 out of 5 average rating, 165 reviews

Zade's Vacation Home w/Private Pool, Jaccuzi, BBQ

We have the perfect spot for a getaway with family and friend!. We are conveniently located 6 minutes from the town of Ocho Rios, 2 mins from the highway and in close proximity to most of the island's attractions. Our property is very modern and equipped with a backyard pool and a BBQ pit. Please feel free to request additional information.

Top guest favourite
A spacious living area features high, slanted ceilings and large windows dressed with soft blue curtains. Comfortable seating is arranged around a central coffee table. A flat-screen TV is mounted on the wall, complemented by decorative vases and colorful cushions.
Bungalow in Richmond Estate
4.96 out of 5 average rating, 138 reviews

❤️ Villa 382• Next to Pool• Full AC• 4 Smart TVs

A relaxed beachy atmosphere with a host of amenities to include: • Next to the pool/ clubhouse/ gym • Fast WiFi • Entire house air conditioned • Netflix/ YouTube in bedrooms & living room • Cable in bedrooms and living room • Self check-in • Barbecue grill • Corn hole • Board games • Fully stocked Kitchen

Popular amenities for Philadelphia holiday rentals

  1. Airbnb
  2. Jamaica
  3. Saint Ann
  4. Philadelphia