Oyster Bay vacation rentals
We found 271 vacation rentals — enter your dates for availability
Select from 17 houses, 21 condos, and other vacation rentals to find the perfect place for your stay in Oyster Bay. Whether you’re traveling with friends, family, or even pets, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.
Vacation rentals with weekly discounts - Oyster Bay
Showing deals for:Nov 21 - Nov 28
Image gallery for Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
9.29.2 out of 10 rating
Wonderful
(12 reviews)
Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
Naples, FL
10% off
Price is CA $266
CA $266
CA $2,446 total
CA $2,446 total
includes taxes & fees
Image gallery for Boaters Paradise : 3 bedroom waterfront home close to downtown Naples Fl.
9.69.6 out of 10 rating
Exceptional
(118 reviews)
Boaters Paradise : 3 bedroom waterfront home close to downtown Naples Fl.
Naples, FL
9% off
Price is CA $898
CA $898
CA $7,908 total
CA $7,908 total
includes taxes & fees
Image gallery for Townhome in the heart of Old Naples - Near 5th Ave, 3rd Street, Beach, Golf Cart
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Townhome in the heart of Old Naples - Near 5th Ave, 3rd Street, Beach, Golf Cart
Naples, FL
5% off
Price is CA $656
CA $656
CA $5,895 total
CA $5,895 total
includes taxes & fees
Image gallery for Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.
Naples, FL
15% off
Price is CA $335
CA $335
CA $2,990 total
CA $2,990 total
includes taxes & fees
Image gallery for Beautiful Downtown located canal home with pool only 1 mile to 5th Ave
1010 out of 10 rating
Exceptional
(21 reviews)
Beautiful Downtown located canal home with pool only 1 mile to 5th Ave
Naples, FL
10% off
Price is CA $361
CA $361
CA $3,366 total
CA $3,366 total
includes taxes & fees
Image gallery for Prime Location in Naples - Walking Distance to 5th Ave & Pet Friendly!
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Prime Location in Naples - Walking Distance to 5th Ave & Pet Friendly!
Naples, FL
10% off
Price is CA $452
CA $452
CA $4,017 total
CA $4,017 total
includes taxes & fees
Image gallery for Location and Lifestyle at its Finest!
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Location and Lifestyle at its Finest!
Naples, FL
10% off
Price is CA $684
CA $684
CA $6,674 total
CA $6,674 total
includes taxes & fees
Image gallery for Royal Palm flat
1010 out of 10 rating
Exceptional
(10 reviews)
Royal Palm flat
Naples, FL
10% off
Price is CA $143
CA $143
CA $1,457 total
CA $1,457 total
includes taxes & fees
Image gallery for Newly Remodeled Cozy Home, Excellent location, 3 miles to beaches and 5th Ave!
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Newly Remodeled Cozy Home, Excellent location, 3 miles to beaches and 5th Ave!
Naples, FL
5% off
Price is CA $263
CA $263
CA $2,512 total
CA $2,512 total
includes taxes & fees
Image gallery for Beautiful Condo In The Heart Of Olde Naples!
9.49.4 out of 10 rating
Exceptional
(39 reviews)
Beautiful Condo In The Heart Of Olde Naples!
Naples, FL
10% off
Price is CA $497
CA $497
CA $4,419 total
CA $4,419 total
includes taxes & fees
Image gallery for Look no Further We have all 5 Stars reviews for a reason at Naples Bay Resort
1010 out of 10 rating
Exceptional
(94 reviews)
Look no Further We have all 5 Stars reviews for a reason at Naples Bay Resort
Naples, FL
10% off
Price is CA $372
CA $372
CA $4,307 total
CA $4,307 total
includes taxes & fees
Image gallery for “Rare Find” Paradise on Naples Bay! In the prestigious Royal Harbor!
1010 out of 10 rating
Exceptional
(9 reviews)
“Rare Find” Paradise on Naples Bay! In the prestigious Royal Harbor!
Naples, FL
5% off
Price is CA $453
CA $453
CA $4,241 total
CA $4,241 total
includes taxes & fees
Image gallery for Keys stilt cottage lower unit
9.69.6 out of 10 rating
Exceptional
(33 reviews)
Keys stilt cottage lower unit
Naples, FL
10% off
Price is CA $116
CA $116
CA $1,189 total
CA $1,189 total
includes taxes & fees
Image gallery for Royal Palm House 2 story home near Naples Bay and Beach
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Royal Palm House 2 story home near Naples Bay and Beach
Naples, FL
10% off
Price is CA $247
CA $247
CA $2,337 total
CA $2,337 total
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
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Chalet
Find the best place to stay - Oyster Bay
Boaters Paradise : 3 bedroom waterfront home close to downtown Naples Fl.
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
118 reviews(118 reviews)
Newly listed Waterfront Townhouse in Old Naples
Sleeps 6 · 2 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
Sleeps 5 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
12 reviews(12 reviews)
Paradise on the Bay!
Sleeps 6 · 3 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Royal Palm House 2 story home near Naples Bay and Beach
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
STUNNING POOL HOME, 4 BEDS/4 BATHS, DOWNTOWN NAPLES, FL
Sleeps 10 · 4 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Top rated rentals - Oyster Bay
Awesome property and resort!
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
We had an amazing week here with our teenagers. Property was exactly as advertised, very clean, and came with all the necessary amenities. Resort facilities were impressive and resort staff were very friendly and professional. Walking/biking distance to beach, great restaurants and shopping.
Kreshka Y.
Stayed Jul 2023
Great location, beautiful property!
1010 out of 10
Exceptionalexceptional
42 reviews(42 reviews)
The condo, amenities and location were wonderful. We highly recommend, we’ll be back!
Terry H.
Stayed Jan 2023
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental in Oyster Bay?
In Oyster Bay, condos are the most popular type of vacation rental, with around 16 available in this charming coastal area. These condos often come equipped with modern amenities such as fully stocked kitchens, open-plan living spaces, and access to communal facilities like pools and fitness centres. Many are situated near local attractions, providing easy access to the scenic waterfront and nearby parks.
Are there any beach house rentals in Oyster Bay?
In Oyster Bay, Florida, there are approximately 85 beach house rentals available, primarily located in charming neighbourhoods close to the waterfront and the picturesque Oyster Bay Harbor. These beach houses typically come equipped with modern amenities, including spacious living areas, fully equipped kitchens, and outdoor decks or patios superb for enjoying the coastal breeze. Many properties also feature private gardens and swimming pools, making them ideal for families or groups looking to relax and enjoy the sun.
How much does it cost to rent a vacation home in Oyster Bay?
Prices for vacation rentals in Oyster Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oyster Bay to more spacious homes.
Are there any discounts for Oyster Bay vacation house rentals?
You can find great discounts on house rentals in Oyster Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Oyster Bay vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oyster Bay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Oyster Bay?
A long-stay vacation rental in Oyster Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Oyster Bay for a vacation rental?
The best time to visit Oyster Bay for a vacation rental is during the peak season from January to March. This period attracts travellers looking to escape colder climates and enjoy the pleasant warmth of Florida. With average temperatures in the low to mid-20s Celsius, it's an ideal time for outdoor activities, including kayaking in the bay, fishing, and exploring the beautiful coastal trails.
January, in particular, is a popular month, as visitors flock to the area for its mild weather and vibrant atmosphere. The stunning beaches and nature parks nearby provide excellent opportunities for relaxation and sightseeing, making it easy to immerse yourself in the natural beauty of Oyster Bay.
If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience with the chance to enjoy the tranquil beaches and local attractions without the crowds, while still benefiting from the warm Florida climate. October is a lovely time to explore the area's charming local eateries and shops at your leisure.
Are there any remote work vacation rentals in Oyster Bay?
In Oyster Bay, there are numerous remote work-friendly vacation rentals available, with around 25 options to choose from. This charming area offers a tranquil environment ideal for those looking to balance work and leisure. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces with desks and office chairs, and some even feature computer monitors, ensuring that you have all the tools needed for productivity during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Oyster Bay vacation rental?
Book your Oyster Bay vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oyster Bay?
In Oyster Bay, visitors can enjoy a selection of attractions that highlight the area's natural beauty and rich history. The scenic Oyster Bay Town Park offers lovely waterfront views and ample space for picnicking and outdoor activities, making it a great spot for families and nature lovers alike. Nearby, the historic Planting Fields Arboretum State Historic Park features beautiful gardens and a stunning mansion, providing a glimpse into the area's past.
Can I change or cancel my Oyster Bay home rental booking on Vrbo?
To find Oyster Bay vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Oyster Bay vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.