Discover Your Perfect Greenwich Vacation Homes

Best Vacation Homes in Greenwich

New
1100 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Pet Friendly House
  • Fireplace/Heating
  • Pet Friendly
  • Air Conditioner
R4,940/Night For 7 Nights R34,573
10.0
Exceptional
(11 Reviews)
2497.23 ft² 8 Guests 4 Bedrooms 2 Bathrooms
House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R6,804/Night For 7 Nights R47,625
New
1 Bedroom 1 Bathroom
Couples Retreat House
  • Hot Tub
  • Pool
  • Balcony/Terrace
R8,563/Night For 7 Nights R59,952
New
1 Bathroom
Family Friendly Hotel
  • Private Pool
  • Fireplace/Heating
  • Pool
R4,715/Night For 7 Nights R33,007
10.0
Exceptional
(8 Reviews)
1205.56 ft² 8 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R5,613/Night For 7 Nights R39,289
10.0
Exceptional
(107 Reviews)
1000 ft² 4 Guests 2 Bedrooms 1 Bathroom
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R3,931/Night For 7 Nights R27,517
10.0
Exceptional
(97 Reviews)
500 ft² 4 Guests 1 Bedroom 1 Bathroom
Ocean View House
  • Private Pool
  • Fireplace/Heating
  • Pool
R7,161/Night For 7 Nights R50,134
10.0
Exceptional
(91 Reviews)
775 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R4,557/Night For 7 Nights R31,896

Greenwich Luxury Rentals

9.6
Exceptional
(33 Reviews)
4329 ft² 10 Guests 4 Bedrooms 5 Bathrooms
Ocean View House
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
R57,823/Night For 7 Nights R404,758
New
5026.75 ft² 10 Guests 5 Bedrooms 6 Bathrooms
Ocean View Villa
  • Oceanfront
  • Hot Tub
  • Pool
R40,922/Night For 7 Nights R286,454
10.0
Exceptional
(17 Reviews)
4706 ft² 12 Guests 6 Bedrooms 5 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Hot Tub
R38,091/Night For 7 Nights R266,633
10.0
Exceptional
(8 Reviews)
5024 ft² 10 Guests 5 Bedrooms 6 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Pool
R35,854/Night For 7 Nights R250,972
10.0
Exceptional
(3 Reviews)
4400 ft² 6 Guests 4 Bedrooms 4 Bathrooms
Family Friendly Condo
  • Hot Tub
  • Fireplace/Heating
  • Pool
R31,290/Night For 7 Nights R219,026
9.8
Exceptional
(15 Reviews)
8 Guests 4 Bedrooms 3 Bathrooms
Ocean View House
  • Hot Tub
  • Fireplace/Heating
  • Ocean View
R21,314/Night For 7 Nights R149,189
10.0
Exceptional
(104 Reviews)
6900 ft² 18 Guests 6 Bedrooms 7 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Hot Tub
R17,871/Night For 7 Nights R125,107
New
1700 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Ocean View House
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
R17,453/Night For 7 Nights R122,177

Greenwich Pet Friendly Vacation Rentals

10.0
Exceptional
(48 Reviews)
1200 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R3,552/Night For 7 Nights R24,856
10.0
Exceptional
(1 Review)
581.25 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Pool
  • Pet Friendly
R3,795/Night For 7 Nights R26,557
New
1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Pet Friendly
  • Air Conditioner
  • Internet
R5,400/Night For 7 Nights R37,807
10.0
Exceptional
(14 Reviews)
1800 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
R5,710/Night For 7 Nights R39,962
9.8
Exceptional
(8 Reviews)
1496.18 ft² 6 Guests 3 Bedrooms 2 Bathrooms
House
  • Pool
  • Balcony/Terrace
  • Pet Friendly
R6,719/Night For 7 Nights R47,035
10.0
Exceptional
(14 Reviews)
585 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Pool
  • Pet Friendly
R3,299/Night For 7 Nights R23,088
10.0
Exceptional
(14 Reviews)
965 ft² 4 Guests 1 Bedroom 1 Bathroom
Ocean View Condo
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
R1,875/Night For 7 Nights R13,135
10.0
Exceptional
(13 Reviews)
960 ft² 3 Guests 1 Bedroom 1 Bathroom
Ocean View Condo
  • Oceanfront
  • Fireplace/Heating
  • Pool
R2,610/Night For 7 Nights R18,272

Greenwich Large Vacation Homes

10.0
Exceptional
(5 Reviews)
740 ft² 4 Guests 1 Bedroom 1 Bathroom
Ocean View Villa
  • Fireplace/Heating
  • Pool
  • Ocean View
R6,040/Night For 7 Nights R42,286
10.0
Exceptional
(1 Review)
1550 ft² 14 Guests 7 Bedrooms 5 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Parking
R4,862/Night For 7 Nights R34,034
10.0
Exceptional
(13 Reviews)
10 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Fireplace/Heating
  • Pool
R8,911/Night For 7 Nights R62,377
10.0
Exceptional
(3 Reviews)
10 Guests 4 Bedrooms 2 Bathrooms
Ocean View House
  • Fireplace/Heating
  • Ocean View
  • Balcony/Terrace
R6,944/Night For 7 Nights R48,618
10.0
Exceptional
(1 Review)
12 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
R11,418/Night For 7 Nights R79,924
10.0
Exceptional
(1 Review)
10 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
R11,236/Night For 7 Nights R78,644
9.8
Exceptional
(12 Reviews)
14 Guests 6 Bedrooms 3 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
R15,535/Night For 7 Nights R108,755
9.8
Exceptional
(9 Reviews)
2100 ft² 12 Guests 5 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R6,328/Night For 7 Nights R44,290

Why Choose Rent By Owner for your Greenwich Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Greenwich

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can significantly enhance your experience, so consider factors such as weather and local events to make the most of your stay in this popular destination.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, you can enjoy a warm escape in this sun-drenched destination, making it an ideal time for outdoor activities and relaxation by the water.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 60°F to 65°F
spring
Spring (March to May)

Springtime brings pleasant weather perfect for exploring the area’s natural beauty and enjoying outdoor leisure activities with comfortable temperatures.

Average Temperature Daytime: 78°F to 85°F - Nighttime: 62°F to 70°F

Off-Season Highlights

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Summer (June to August)

The hot summer months see fewer visitors, providing a more relaxed experience as you savor the warm weather and quieter surroundings.

Average Temperature Daytime: 88°F to 92°F - Nighttime: 74°F to 78°F
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Fall (September to November)

Autumn offers milder temperatures and less crowded conditions, making it an excellent time to explore and enjoy the region’s serene atmosphere.

Average Temperature Daytime: 80°F to 85°F - Nighttime: 66°F to 72°F

Weekly Weather Forecast for Greenwich

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private swimming pool to cool off during warm Florida days.
  • Relax in a spacious outdoor seating area perfect for gatherings or sunset views.
  • Take advantage of the lush landscaped gardens surrounding your rental for peaceful strolls.
  • Make use of an outdoor grill or barbecue for memorable cookouts with family and friends.
  • Unwind in a covered patio or veranda that offers shade and comfort outdoors.
  • Access nearby outdoor recreational facilities, such as tennis courts or walking trails.
  • Experience the convenience of ample parking spaces ideal for exploring the region's attractions.
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Family Activities

  • Jupiter Inlet Lighthouse & Museum: Explore this iconic lighthouse and museum to learn about the area's maritime history and enjoy panoramic views of the region.
  • Relax and play on this family-friendly beach offering soft sands, picnic areas, and gentle waves perfect for children.
  • Discover nature trails, canoe rentals, and outdoor activities that allow your family to immerse in the scenic beauty of the local landscape.
  • Experience shopping, dining, and entertainment options within a vibrant waterfront setting ideal for family outings.
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Adult Activities

  • Golfing at Jupiter Hills Golf Course: Enjoy a round of top-tier golf on picturesque courses that showcase the region's lush landscapes and expert design.
  • Exploring the Jupiter Inlet Lighthouse & Museum: Discover local history and take in stunning views from this iconic lighthouse, a must-visit attraction here.
  • Relaxing at the Beaches of Jupiter: Spend your days lounging or swimming along pristine shoreline areas known for their natural beauty and serene ambiance.
  • Fishing Excursions in Jupiter: Embark on deep-sea or freshwater fishing trips that provide memorable experiences amid the region’s abundant aquatic life.

Greenwich Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take advantage of the region's well-known outdoor activities and natural beauty to create memorable experiences during your stay.
  • Choose a Prime Location: Select a vacation rental in a convenient spot close to the area's key attractions and amenities for effortless exploration.
  • Engage with Community Events: Participate in local events or markets to immerse yourself in the culture and enjoy authentic regional offerings.
  • Plan Outdoor Activities: Make the most of the pleasant weather by scheduling outdoor adventures such as boating, fishing, or relaxing at nearby beaches.

Transportation Options

  • Jupiter Transit Service: Conveniently connect you to the regional transportation network, making it easy to explore this coastal destination and its surrounding areas.
  • Local Bus Services: These affordable buses operate within the region, offering a reliable way to get around when staying in one of the area's vacation rentals.
  • Taxi and Rideshare Options: Popular ride-hailing services provide quick and flexible transportation directly from your accommodations to local attractions in here.
  • Car Rentals: Renting a vehicle is an excellent choice for exploring the region at your own pace, especially when staying near key destinations or scenic spots.

Local Customs Options

  • Respect for the Environment: Locals here take pride in preserving the natural beauty of the area, encouraging visitors to engage in eco-friendly practices during their stay.
  • Celebration of Local Festivals: Participating in traditional festivals and events is a cherished custom that offers insight into the region's rich cultural heritage.
  • Greeting Etiquette: A friendly handshake or a warm smile is the usual way residents welcome newcomers and guests in this coastal community.
  • Community Engagement: Supporting local businesses and participating in neighborhood activities are valued customs that foster a sense of belonging here.

Frequently Asked Questions About Greenwich?

2. How many vacation rentals have private pools in Greenwich?

There are 48 vacation rentals with private pools near Greenwich. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Greenwich are best for families?

If you are looking for a family-friendly vacation home in Greenwich, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Greenwich:

4. How many Rentbyowner vacation rentals are available in Greenwich?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 316 in the Greenwich area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Greenwich. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the individual host or property owner. To understand the specific terms, please review the listing details or contact the owner directly before booking.

6. Are there any hidden fees associated with booking a vacation rental here?

Additional fees, such as cleaning or service charges, are typically outlined in the listing. We recommend reading the full description or reaching out to the host for clarity on any extra costs.

7. How do I ensure my booking is secure and reliable?

Booking through trusted platforms ensures your reservation is protected. Always verify the host’s reviews and ratings, and communicate through the platform’s messaging system for a safe experience.

8. What amenities can I expect from vacation rentals in this region?

Amenities vary by property but often include essentials like Wi-Fi, air conditioning, and kitchen facilities. Details about available amenities are listed in each property’s description.

9. Is it possible to make special requests or modifications to my stay?

Many hosts accommodate special requests; however, these should be discussed directly with the owner prior to booking. Check the listing for any notes on custom arrangements or contact the owner for specific needs.

Greenwich Top Rated Vacation Rentals

10.0
Exceptional
(69 Reviews)
6 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
R5,403/Night For 7 Nights R37,823
10.0
Exceptional
(67 Reviews)
750 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
R6,387/Night For 7 Nights R44,711
10.0
Exceptional
(43 Reviews)
6 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
R5,374/Night For 7 Nights R37,621
10.0
Exceptional
(43 Reviews)
1350 ft² 5 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
R4,700/Night For 7 Nights R32,906
10.0
Exceptional
(38 Reviews)
2060 ft² 8 Guests 4 Bedrooms 3 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
R9,209/Night For 7 Nights R64,465
10.0
Exceptional
(33 Reviews)
1600 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
R8,498/Night For 7 Nights R59,497
10.0
Exceptional
(28 Reviews)
1852 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
R5,526/Night For 7 Nights R38,682
10.0
Exceptional
(23 Reviews)
8 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Hot Tub
R7,293/Night For 7 Nights R51,060