Family Friendly Villa Collection

Family Friendly Villa Collection

We want to make your family villa vacation as comfortable as possible. Our villa specialists have handpicked properties that are particularly accommodating for families with young children. They can offer detailed insights into each property, including specifics about swimming pool depth, secure fencing, and other child-friendly features like playgrounds, kid’s clubs, and babysitting services. We can help you find the perfect family-friendly property for your vacation.

Smugglers Cove is great for beach lovers, because the guests have direct access to Paynes Bay. The villa is spacious and beautifully decorated, and has a friendly staff. There's several ...
Paynes Bay Beach is just below the balcony at Smugglers Cove #4

Smugglers Cove #4

3 Bedrooms
3 Bathrooms
Barbados
  • Beachfront
  • AC
Details
Crescent Beach villa sits in beautiful, peaceful Bequia, with a view of the beach below. You’ll love listening to the gentle waves and breeze blowing through, and the hillside ...
Crescent Beach Villa is located above Crescent Beach and has amazing ocean views
1 BR rate.

Crescent Beach Villa

3 Bedrooms
3 Bathrooms
Bequia, St. Vincent & Grenadines
  • Pool
  • AC
Details
Casa Luna 17 is great for families who want a bit of privacy at a great price. Kids can stay on the lower level in two suites, and the basement-level bathroom ...
There is an amazing beach cove at Casa Luna Villas

Casa Luna 17

3 Bedrooms
4 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • AC
  • Resort Villa
Details
Edge of Paradise is a great choice for three couples who want to relax by Grace Bay. The villa comes with a cooler, and an electric golf cart so you ...
Edge of Paradise is located just a few minutes from Grace Bay Beach

Edge of Paradise

3 Bedrooms
3 Bathrooms
Leeward, Turks and Caicos
  • Near Beach
  • Pool
  • AC
Details
If you love Grace Bay and Smith's Reef, you'll love Sandpebble. Its right by the sea, near Turks and Caicos' best snorkeling, and has gorgeous ocean views. There's a good ...
Aerial view of the Sandpebble property

Sandpebble

3 Bedrooms
3+ Bathrooms
Grace Bay, Turks and Caicos
  • Beachfront
  • Pool
  • AC
Details
Tradewinds is ideal for three couples who want to vacation on Grace Bay without sacrificing privacy. The villa is surrounded by thick gardens and has a private path to the ...
Tradewinds Villa is located near Grace Bay Beach
Specials.

Tradewinds

3 Bedrooms
3 Bathrooms
Grace Bay, Turks and Caicos
  • Near Beach
  • Pool
  • AC
Details
Seashells is a great choice for a beachfront family vacation. It's steps away from the sea, has three-stories of space, and offers tons of outdoor space. The pool isn't that ...
Seashells Villa is set on a beautiful stretch of beach

Seashells

3 Bedrooms
3+ Bathrooms
Barbados
  • Beachfront
  • Pool
  • AC
Details
Porters is a family-friendly villa with a great location, elegant design, and gorgeous gardens. The villa's three bedrooms are all kings or twins that can be made up as kings, ...
Porters Villa is located in St. James

Porters

3 Bedrooms
3 Bathrooms
Barbados
  • Near Beach
  • Pool
  • AC
Details
On The Rocks has a classic, beach house vibe in one of Turks and Caicos's most underrated areas. Chalk Sound is absolutely gorgeous, well-developed, and famous solely with locals and ...
On the Rocks is located in Silly Creek on Chalk Sound

On the Rocks

3 Bedrooms
3 Bathrooms
Chalk Sound, Turks and Caicos
  • Pool
  • AC
Details
This three-bedroom resort villa has everything you need for an easy family vacation. Everything has been thought of for you, from the kitchen gadgets to the complimentary cribs to the ...
Seafire Resort

The Residences at Seafire 3 Bedroom South

3 Bedrooms
3+ Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • AC
Details
If you’re looking for an Anguilla beachfront rental, this resort villa is worth a look. It’s right on Meads Bay, one of the island’s most gorgeous beaches, ...
Tranquility Beach - Beachfront Penthouse Villa is located on Meads Bay Beach
Specials.

Tranquility Beach - Beachfront Penthouse

3 Bedrooms
3+ Bathrooms
Anguilla
  • Beachfront
  • AC
  • Resort Villa
Details
Viceroy Sugar Beach's Three Bedroom Villa Residence is the ideal rental for a luxurious beachfront experience. The beach is steps from the veranda, and the resort's endless activities are minutes ...
The Viceroy 3 Bedroom Villa Residences are set in the foothills of the Pitons and the Caribbean Sea

Viceroy Sugar Beach - Three Bedroom Villa Residence - Beachfront

3 Bedrooms
3+ Bathrooms
Soufriere, St. Lucia
  • Beachfront
  • Pool
  • AC
Details
This gorgeous villa is perfect if you want to be near Seven Mile Beach, but away from the crowds. There’s tons to do at and around the villa, so ...
Casa Luna 4 is located in the resort community along the coastline just south of Seven Mile Beach

Casa Luna 4

3 Bedrooms
4 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • AC
  • Resort Villa
Details
This spacious, beachfront villa has a convenient location within walking distance of dining, attractions, and excursions. Even though Rum Point Beach and Cayman Kai are minutes away, Les Jalousies has ...
Les Jalousies is located in Cayman Kai

Les Jalousies

3 Bedrooms
3 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • Pool
  • AC
Details
Love this sweet villa that sits just above the quaint fishing village of Corossol. It's perfect for a family with all three bedrooms located on the same level, a super ...
AKA Villa is located in Corossol with great views of Gustavia Harbor
1 BR rate.

Aka Villa

3 Bedrooms
2 Bathrooms
Corossol, St. Barts
  • Pool
  • AC
Details
Modern design, beach access, and three bedrooms make this penthouse the perfect rental for your next vacation. It’s right on Meads Bay, which is one of the island’s ...
Tranquility Beach Anguilla is located on Meads Bay Beach
Specials.

Tranquility Beach - Penthouse

3 Bedrooms
3+ Bathrooms
Anguilla
  • Beachfront
  • AC
  • Resort Villa
Details
Sapphire Beach 401 has easy beach access near great snorkeling, restaurants, and activities. It’s a great choice for your next family vacation, because there’s a king suite, a queen ...
Sapphire Beach 401 has views right over the beach
2 BR rate.

Sapphire Beach 401

3 Bedrooms
3 Bathrooms
Barbados
  • Beachfront
  • AC
  • Resort Villa
Details
If you want gorgeous views, interiors, and design, Adharra is a great choice. This Pointe Milou villa has a quiet location near the island's hot spots, and the views are ...
Infinity Villa is located on a hilltop in Pointe Milou overlooking Lorient Bay
2 BR rate.

Adharra

3 Bedrooms
3 Bathrooms
Pointe Milou, St. Barts
  • Pool
  • AC
Details
Sailrock Resort is a great part of the island to stay on if you want tranquility, convenience, and seclusion. The resort's neighborhood is low-density and off the beaten path, so ...
Sailrock Resort Oceanfront Coral Villa is located oceanfront on the Sailrock Peninsula

Sailrock Resort Oceanfront Coral Villa

3 Bedrooms
3 Bathrooms
South Caicos, Turks and Caicos
  • Pool
  • AC
  • Resort Villa
Details
Vacationing with teens? This is the perfect villa. This two-bedroom beach house and one-bedroom cottage is incredible for families who want to be near all the action without spending their ...
Beach Enclave Long Bay is located on the southeastern edge of Providenciales

BE - 2 Bedroom Beach Front Plus 1 Bedroom Cottage at Long Bay

3 Bedrooms
3+ Bathrooms
Long Bay, Turks and Caicos
  • Beachfront
  • Pool
  • AC
  • Resort Villa
Details
The Cottage at Meads Bay is extremely popular due to it's direct beach access on one of the island’s most beautiful beaches. It offers three spacious bedrooms, an updated ...
The Cottage at Meads Bay photo

The Cottage at Meads Bay

3 Bedrooms
3+ Bathrooms
Anguilla
  • Beachfront
  • AC
Details
No Limit is a charming villa with gorgeous ocean views and a spacious exterior with several lounging and dining areas. You’ll never want to go inside! There are two ...
No Limit is located on a hillside in Terres Basses overlooking Baie Longue
2 BR rate.
Specials.

No Limit

3 Bedrooms
3+ Bathrooms
Terres Basses (French side), St. Martin
  • Pool
  • AC
Details
Casa Luna 16 has next-level benefits for anyone seeking privacy, resort amenities, and luxury. The exterior is tricked out for entertaining and dining, and the resort's pool and barefoot beach are ...
Casa Luna 16 is located in the exclusive resort at the very end of Seven Mile Beach

Casa Luna 16

3 Bedrooms
3 Bathrooms
Grand Cayman, Cayman
  • Beachfront
  • AC
  • Resort Villa
Details
Blu in Turks and Caicos is definitely the place to be! With its stunning sunsets and a mere hop, skip, and a jump to the beach, you'll be sure to ...
Villa Blu is located steps from Grace Bay beach

Blu

3 Bedrooms
3 Bathrooms
Grace Bay, Turks and Caicos
  • Pool
  • AC
Details
Cheemaun Beach Villa is ideal for family holidays and romantic retreats. Convenience and excitement are combined at this beachfront property on Oil Nut Bay, just steps from the resort beach ...
Cheemaun Beach Villa is located Steps from Oil Nut Bay’s white sand beach

Cheemaun Beach Villa

3 Bedrooms
3+ Bathrooms
Virgin Gorda, BVI, British Virgin Islands
  • Beachfront
  • Pool
  • AC
  • Resort Villa
Details
With its prime water front location, Belvedere Villa in North Caicos offers an amazing three-bedroom retreat boasting stunning ocean views, a private pool, and a sense of calm and serenity. ...
Belvedere Villa is located in North Caicos

Belvedere

3 Bedrooms
3+ Bathrooms
North Caicos, Turks and Caicos
  • Pool
  • AC
Details
Escape to Driftwood Villa and let yourself be captivated by the mesmerizing views of St. John. With its hillside location in Ditleff Point, this luxurious retreat offers you breathtaking vistas ...
Driftwood Villa on Ditleff Point

Driftwood

3 Bedrooms
4+ Bathrooms
Rendezvous Bay, St. John
  • Pool
  • AC
Details
Beachi at Coral Cove is the ultimate beachfront property in Barbados. With an amazing terrace offering breathtaking views, three bedrooms, and direct access to the beach, this is the perfect ...
Aerial view of beachfront access at Beachi - Coral Cove #9

Beachi

3 Bedrooms
3 Bathrooms
Barbados
  • Beachfront
  • AC
Details
Osprey villa has gorgeous sunset views and outdoor amenities perfect for a family vacation. The waterfront location is enhanced by a seaside deck, kayaks, and an oceanfront gazebo. There's a ...
Osprey is located on the ocean side of Chalk Sound

Osprey Villa

3 Bedrooms
3 Bathrooms
Taylor Bay-Sapodilla Bay, Turks and Caicos
  • Pool
  • AC
Details
Caribbean vacations offer much more than you might imagine, especially if you have never heard about the wonderful accommodation options. One is the beautiful Hummingbird Villa of St. Lucia. This ...
Hummingbird Villa photo

Hummingbird Villa

3 Bedrooms
3 Bathrooms
Cap Estate, St. Lucia
  • Pool
Details
The beautifully landscaped and stylish Saline Reef is a great vacation spot for families with children over 12, or adults who want an exclusive get-away location. The views from this three-bedroom ...
Saline Reef Villa photo
2 BR rate.

Saline Reef Villa

3 Bedrooms
3 Bathrooms
Cap Estate, St. Lucia
  • Near Beach
  • Pool
  • AC
Details
Terres Basses is known as one of St. Martin's nicest areas, and Callisto does not disappoint. The villa consists of 3 bedrooms with en-suite bathrooms, a living room with a piano ...
Callisto Villa is located on a hillside in Terres Basses and enjoys sunset views over Baie Longue
2 BR rate.
Specials.

Callisto

3 Bedrooms
3+ Bathrooms
Terres Basses (French side), St. Martin
  • Pool
  • AC
Details
Anchorage Villa is a warm, sun-drenched property with a spacious living room and an open-concept dining area. The housekeeper prepares breakfast and lunch every day, so you can explore the ...
Anchorage Villa is on the western end of the Sandy Lane Estate

Anchorage Villa

3 Bedrooms
3 Bathrooms
Barbados
  • Pool
  • AC
Details
Guests will be immediately taken with the sleek, peaceful influence of Japan when they enter Plein Ciel Villa. The high vaulted ceilings and tile floors keep the villa cool on ...
Plein Ciel Villa photo
2 BR rate.

Plein Ciel Villa

3 Bedrooms
2 Bathrooms
Marigot, St. Barts
  • Pool
  • AC
Details
You're bound to enjoy the gardens, but there are many other features in this estate to make you feel at home. The high vaulted ceilings and tile floors keep the ...
Canefield house sits on a lovely hillside in the heart of Tortola
2 BR rate.

Canefield House

3 Bedrooms
3+ Bathrooms
Tortola, BVI, British Virgin Islands
  • Pool
  • AC
Details
Abby Villa is the perfect St. Barts getaway for three couples who want a cozy, peaceful location near multiple beaches. This hillside beauty has chic, white interiors, top-notch appliances, and ...
Abby Villa photo
2 BR rate.

Abby Villa

3 Bedrooms
3 Bathrooms
Vitet, St. Barts
  • Pool
  • AC
Details
At Rocky Point, you have the opportunity for privacy and excitement, as well as spectacular ocean views. This three-bedroom villa offers two acres of sand and beach, tropical vegetation, and ...
The pool at Rocky Point villa!

Rocky Point at COMO Parrot Cay

3 Bedrooms
3 Bathrooms
Parrot Cay, Turks and Caicos
  • Beachfront
  • Pool
  • AC
  • Resort Villa
Details
Terres Basses in St. Martin is known for fine beaches and great scenery, and La Magnolia Villa is situated to enjoy these. The home overlooks the ocean, so the water ...
La Magnolia sits on a hilltop over Baie Longue with a great view of the ocean
1, 2 BR rates.
Specials.

La Magnolia Villa

3 Bedrooms
3 Bathrooms
Terres Basses (French side), St. Martin
  • Pool
  • AC
Details
This villa is great for a few couples or a family. All three bedrooms have ensuite bathrooms, and two are kings while the third has two twins. There's a common ...
Sweet Return Villa is located near the golf course and Rendezvous Bay
2 BR rate.

Sweet Return Villa

3 Bedrooms
3 Bathrooms
Anguilla
  • Pool
  • AC
Details
If you're ready for a Caribbean escape with views galore, then Eaglesnest is the place for you. It's location on Contant Point gives you panoramic views of Great Cruz Bay, ...
Eaglesnest is located on a hillside overlooking Great Cruz Bay
1, 2 BR rates.

Eaglesnest Villa

3 Bedrooms
3 Bathrooms
Great Cruz Bay, St. John
  • Pool
  • AC
Details
Casawapa is great for couples traveling together or family vacations. The rooms are equal in size and separated by the living area, which gives your guests plenty of privacy. Outside, ...
The One Villa sits on the Colombier hillside overlooking the Caribbean
2 BR rate.

The One

3 Bedrooms
3 Bathrooms
Colombier, St. Barts
  • Pool
  • AC
Details
Located on a hillside in Marigot, Au Couer du Rocher is an open home. It is stylishly furnished and also includes partial air-conditioning, a fully equipped kitchen, a large living ...
Au Coeur du Rocher is located on a on a hillside in Marigot
1, 2 BR rates.

Au Coeur du Rocher

3 Bedrooms
3+ Bathrooms
Marigot, St. Barts
  • Pool
  • AC
Details
Dasha Villa is quickly building a roster of loyal fans. A recent visitor summed up her stay at the villa by saying, 'It was just what we needed! Perfect, relaxing, ...
Dasha Villa is located on a hillside overlooking Views of Gouverneur
1, 2 BR rates.

Dasha Villa

3 Bedrooms
3 Bathrooms
Lurin, St. Barts
  • Pool
  • AC
Details
Whether you want to relax by the pool for your entire vacation, or you're an adventurer who wants a lot of action, Victoria Villa is the place to stay. In ...
Victoria Villa is located in the Oyster Pond neighborhood on a hillside overlooking Orient Bay
Specials.

Victoria Villa

3 Bedrooms
3+ Bathrooms
Oyster Pond (Dutch side), St. Martin
  • Pool
  • AC
Details
Mer Soleil is a contemporary villa located in Gouverneur just a five minute drive to the pristine beach. Stop and have a long lunch at the Santa Fe restaurant, then ...
Amazing views from the deck
2 BR rate.

Mer Soleil

3 Bedrooms
3 Bathrooms
Gouverneur, St. Barts
  • Pool
  • AC
Details
Harmony House is an elegantly furnished, fully-equipped, three-bedroom villa with everything you need for a relaxing Barbados getaway. The bedrooms are spacious and come with ensuite bathrooms and private balconies. ...
Harmony House is just steps away from Gibbes Beach

Harmony House

3 Bedrooms
3+ Bathrooms
Barbados
  • Beachfront
  • Pool
  • AC
Details
Reef Pearl Villa, with it's private swimming pool, relaxing hammock, and perfect beachfront location is the ideal getaway spot for family or group of friends. Located a quick minutes' walk ...
Ocean kayaks - Ask for availability
2 BR rate.

Reef Pearl Villa

3 Bedrooms
3 Bathrooms
Grace Bay, Turks and Caicos
  • Beachfront
  • Pool
  • AC
Details
Conch Beach has everything you could possibly want in a family vacation rental, from the bedrooms to the design to the location. For starters, the Master Suite is huge and ...
Conch Beach Villa is located on the beautiful Grace Bay Beach

Conch Beach Villa

3 Bedrooms
3 Bathrooms
Grace Bay, Turks and Caicos
  • Beachfront
  • Pool
  • AC
Details
You can see the ocean from every room in this beachfront villa, and natural light enhances the tropical vibe. You can sunbathes on a cushioned lounger, dangle your feet in ...
Fathom's End - Mahogany Bay is located right on the beach at Mahogany Bay

Fathom's End - Mahogany Bay

3 Bedrooms
3+ Bathrooms
Barbados
  • Beachfront
  • Pool
  • AC
Details
Sunset Reach has the benefit of being directly on Mullins Beach, a crowd-favorite for snorkeling, water sports, and its famed beach bar. The villa features 3 bedrooms, making it perfect for ...
Sunset Reach sits a few feet from the sea on Mullins Beach
2 BR rate.

Sunset Reach Villa

3 Bedrooms
3 Bathrooms
Barbados
  • Beachfront
  • AC
Details
Blue Lagoon Villa is a family friendly, wheelchair accessible villa that can easily sleep up to ten people. With a classic master bedroom and unique guest suites, everyone in your ...
Blue Lagoon Villa photo
2 BR rate.

Blue Lagoon Villa

3 Bedrooms
3 Bathrooms
Virgin Gorda, BVI, British Virgin Islands
  • Near Beach
  • Pool
  • AC
Details
This villa would be so fun for your next family vacation. Kids will love the pool, teens will love the home entertainment system and tanning chairs, and you'll love the ...
Bel'Ombre photo
1, 2 BR rates.

Bel'Ombre

3 Bedrooms
3 Bathrooms
Marigot, St. Barts
  • Pool
  • AC
Details
Experience luxury living at Villa Buena, a modern cliffside retreat near San José. Marvel at panoramic views of Es Torrent bay from terraced gardens and a heated infinity pool. Inside, ...
Villa Buena photo

Villa Buena

3 Bedrooms
4 Bathrooms
Ibiza, Spain
  • Pool
  • AC
Details
Experience the ultimate island getaway at Maxi Cooper in the British Virgin Islands. Revel in the stunning 180 degree ocean views while lounging on ample outdoor space with your favorite cocktail ...
Maxi Cooper Villa in Tortola

Maxi Cooper

3 Bedrooms
3+ Bathrooms
Tortola, BVI, British Virgin Islands
  • Pool
  • AC
Details
Sol e Luna is very private with gardens that surround the house giving guests the option of dressing or not. The large, open interiors also make it an ideal spot ...
Sol e Luna is located in the desirable Terres Basses
1, 2 BR rates.
Specials.

Sol e Luna Villa

3 Bedrooms
3 Bathrooms
Terres Basses (French side), St. Martin
  • Pool
  • AC
Details
Panarea Villa is truly beautiful, with a great housekeeper and lush gardens all around. I think this villa is ideal for a casual, laid-back Caribbean vacation, especially for young families ...
Panarea is located in Anguilla's West End, just minutes away from the island's most beautiful beache
1, 2 BR rates.

Panarea Villa

3 Bedrooms
3 Bathrooms
Anguilla
  • Near Beach
  • Pool
  • AC
Details
Tuscany Resort is one of my favorite properties on Turks and Caicos. At WhereToStay.com, we only list resorts that feel like a private villa. Tuscany made our list because ...
The Tuscany Resort is located on East Grace Bay Beach
1, 2 BR rates.
Specials.

Tuscany

3 Bedrooms
3 Bathrooms
Grace Bay, Turks and Caicos
  • Beachfront
  • Pool
  • AC
  • Resort Villa
Details
Located within walking distance to a grocery store and restaurants, Ecoute les Vagues sits right on Flamands Beach, giving guests easy access to swimming, snorkeling, and sunbathing galore. The villa ...
Ecoute les Vagues is located right on the beach in Flamands Bay

Ecoute les Vagues

3 Bedrooms
2 Bathrooms
Flamands, St. Barts
  • Beachfront
  • Pool
  • AC
Details
Sea Bird is a one-of-a-kind villa in Mont Jean, St. Bart's, with 3 bedrooms, a full kitchen, and large living areas for lounging, watching TV, or enjoying meals. The master bedroom ...
Sea Bird Villa is located on a hilltop in Mont Jean overlooking the Caribbean
1, 2 BR rates.

Sea Bird Villa

3 Bedrooms
3 Bathrooms
Mont Jean, St. Barts
  • Pool
Details
Your family will love staying at The Harbour #17. This brightly colored home is right on the harbor and nestled in the island's most happening bay. You can walk to everything, ...
The Harbour #17 is located in the Harbour Townhomes overlooking the harbour on Rodney Bay
2 BR rate.

The Harbour #17

3 Bedrooms
3+ Bathrooms
Rodney Bay, St. Lucia
  • Near Beach
  • AC
  • Resort Villa
Details