Entire home
🏖️Private Pool with Backyard Oasis-Canal Front-Osprey Retreat🏖️
Photo gallery for 🏖️Private Pool with Backyard Oasis-Canal Front-Osprey Retreat🏖️





Reviews
6.06.0 out of 10
Popular amenities
- Balcony
- Private pool
- Barbecue grill
- Air-conditioning
- Refrigerator
- Washing machine
Explore the area

Fort Myers Beach, FL
- Sterling Ave BeachPlace, Sterling Ave Beach11 min walk
- Estero Boulevard BeachPlace, Estero Boulevard Beach12 min walk
- Castle BeachPlace, Castle Beach4 min drive
- Fort Myers, FL (RSW-Southwest Florida Intl.)Airport, Fort Myers, FL (RSW-Southwest Florida Intl.)58 min drive
Rooms & beds
4 bedrooms (sleeps 8)
1st Floor In-Law Suite Bedroom
1 King Bed
2nd Floor Guest Bedroom
1 Queen Bed
2nd Floor Guest Bedroom
2 Single Beds
2nd Floor Master Bedroom
1 King Bed
3 bathrooms
Guest Bathroom
Guest Bathroom
Master Bathroom
Spaces
Deck or patio
Kitchen
Balcony
About this property
🏖️Private Pool with Backyard Oasis-Canal Front-Osprey Retreat🏖️
Top Reasons to Book Osprey Retreat:
* Gorgeous, Canal Front Home with Stunning Water Views
* Large Freeform Private Pool
* Pet Friendly (Additional Fees Apply)
* Short, Easy Walk to the Beach (approx. 0.2 miles)
* Indoor Porch and Balcony
* Dock Available for Securing Jet Skis, Paddle Boards, or a Kayak
* Professionally Managed
Welcome to Osprey Retreat—a peaceful poolside haven designed with extended families in mind. This 4-bedroom, 3-bath home features a main-level living space upstairs with 3 bedrooms, 2 bathrooms, a fully stocked kitchen, and open living and dining areas that open to bay and pool views. The private in-law suite downstairs offers a separate entrance, its own kitchen, living area, bedroom, and bath—perfect for grandparents or guests wanting extra space. Lounge by the pool, dine al fresco, or watch tropical birds by the bay. Just a 5-minute stroll to the beach, and there’s even a wagon for your chairs and gear!
The Bed Setup:
1st Floor In-Law Suite
Guest Bedroom: King Bed with Private Bathroom
2nd Floor
Master Bedroom: King Bed
Guest Bedroom: Queen Bed
Guest Bedroom: Twin Bed + Twin Daybed
NOTE: Access to the downstairs level is through the garage. Renters will have access to the garage, but not for cars, as the owner keeps an extra car in the garage for their use when they are here. We ask guests to please rinse (outdoor shower) off before entering the pool to remove tanning lotions and debris.
The home does have a spillover spa, but it currently is out of order.
**If you are traveling with a pet, please call the reservations team with the within 24 hours of placing your reservation. Guests are responsible for paying a non-refundable pet fee for dogs under 30lbs is $200 per dog, dogs above 30lbs is $300 per dog.*
Area Activities:
Welcome to Fort Myers Beach! There are multiple state parks nearby that are waiting for your adventures. Jump on the trolley to take you south to the secluded Lover's Key State Park or go north to Bowditch Point Park. The Fish Tale Marina offers boat rentals and dockage for those wanting to get out on the water. Travel around the island in style in a rented Moke or golf cart. Trolley service is also available from Estero Boulevard to the Times Square area, the central hub of Fort Myers Beach. Several restaurants, shops, and bars have come back since the hurricane. If a day trip is what you are looking for check out the Key West Express for an unforgettable trip to Key West. Don’t forget to see Sanibel Lighthouse which is less than 15 miles away! Please note that the area is currently rebuilding after Hurricane Ian. Despite the changes, the island continues to get better and better, inviting you to bask in the sun, sand, and amazing sunsets once again. As local restaurants continue to reopen, you'll have lots of opportunities for entertainment and dining experiences. We're excited to welcome you back.
21591 Madera Rd
Beach Access 17A
STR 26-0355
* Gorgeous, Canal Front Home with Stunning Water Views
* Large Freeform Private Pool
* Pet Friendly (Additional Fees Apply)
* Short, Easy Walk to the Beach (approx. 0.2 miles)
* Indoor Porch and Balcony
* Dock Available for Securing Jet Skis, Paddle Boards, or a Kayak
* Professionally Managed
Welcome to Osprey Retreat—a peaceful poolside haven designed with extended families in mind. This 4-bedroom, 3-bath home features a main-level living space upstairs with 3 bedrooms, 2 bathrooms, a fully stocked kitchen, and open living and dining areas that open to bay and pool views. The private in-law suite downstairs offers a separate entrance, its own kitchen, living area, bedroom, and bath—perfect for grandparents or guests wanting extra space. Lounge by the pool, dine al fresco, or watch tropical birds by the bay. Just a 5-minute stroll to the beach, and there’s even a wagon for your chairs and gear!
The Bed Setup:
1st Floor In-Law Suite
Guest Bedroom: King Bed with Private Bathroom
2nd Floor
Master Bedroom: King Bed
Guest Bedroom: Queen Bed
Guest Bedroom: Twin Bed + Twin Daybed
NOTE: Access to the downstairs level is through the garage. Renters will have access to the garage, but not for cars, as the owner keeps an extra car in the garage for their use when they are here. We ask guests to please rinse (outdoor shower) off before entering the pool to remove tanning lotions and debris.
The home does have a spillover spa, but it currently is out of order.
**If you are traveling with a pet, please call the reservations team with the within 24 hours of placing your reservation. Guests are responsible for paying a non-refundable pet fee for dogs under 30lbs is $200 per dog, dogs above 30lbs is $300 per dog.*
Area Activities:
Welcome to Fort Myers Beach! There are multiple state parks nearby that are waiting for your adventures. Jump on the trolley to take you south to the secluded Lover's Key State Park or go north to Bowditch Point Park. The Fish Tale Marina offers boat rentals and dockage for those wanting to get out on the water. Travel around the island in style in a rented Moke or golf cart. Trolley service is also available from Estero Boulevard to the Times Square area, the central hub of Fort Myers Beach. Several restaurants, shops, and bars have come back since the hurricane. If a day trip is what you are looking for check out the Key West Express for an unforgettable trip to Key West. Don’t forget to see Sanibel Lighthouse which is less than 15 miles away! Please note that the area is currently rebuilding after Hurricane Ian. Despite the changes, the island continues to get better and better, inviting you to bask in the sun, sand, and amazing sunsets once again. As local restaurants continue to reopen, you'll have lots of opportunities for entertainment and dining experiences. We're excited to welcome you back.
21591 Madera Rd
Beach Access 17A
STR 26-0355
Our prices include all fees. No hidden fees.
Add dates for prices
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Waterfront Luxury | Walk to Beach | Heated Pool
South Island
Waterfront Luxury | Walk to Beach | Heated Pool
South Island
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (74 reviews)
10/10
Exceptional
(74 reviews)

End of cul-de-sac! 4-bed 3 bath South Facing spill over spa pool. 2 king suites
Pelican
End of cul-de-sac! 4-bed 3 bath South Facing spill over spa pool. 2 king suites
Pelican
- Pool
- Hot tub
- Kitchen
- Washing machine
9.8 out of 10, Exceptional, (36 reviews)
9.8/10
Exceptional
(36 reviews)

Times Square Gem! 4BR Canal front home, private Pool/Spa, Sleeps 12
Fort Myers Beach
Times Square Gem! 4BR Canal front home, private Pool/Spa, Sleeps 12
Fort Myers Beach
- Pool
- Hot tub
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (124 reviews)
10/10
Exceptional
(124 reviews)

Family Friendly Beach Home with Large Heated Pool
Fort Myers Beach
Family Friendly Beach Home with Large Heated Pool
Fort Myers Beach
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (160 reviews)
10/10
Exceptional
(160 reviews)

Coastal Luxury Oasis: Private Saltwater Pool & Beach Access
Mid Island
Coastal Luxury Oasis: Private Saltwater Pool & Beach Access
Mid Island
- Ocean view
- Pool
- Kitchen
- Washing machine
9.4 out of 10, Exceptional, (91 reviews)
9.4/10
Exceptional
(91 reviews)

Luxe Canal Home, Boat Rental, Walk to Cape Harbour
Pelican
Luxe Canal Home, Boat Rental, Walk to Cape Harbour
Pelican
- Pool
- Hot tub
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (50 reviews)
10/10
Exceptional
(50 reviews)

WALK TO BEACH! - Luxury Waterfront w/4 ensuites, Pool/Spa, Bikes, Kayaks, Dock/ Direct Gulf Access
Yacht Club
WALK TO BEACH! - Luxury Waterfront w/4 ensuites, Pool/Spa, Bikes, Kayaks, Dock/ Direct Gulf Access
Yacht Club
- Pool
- Hot tub
- Kitchen
- Washing machine
9.6 out of 10, Exceptional, (94 reviews)
9.6/10
Exceptional
(94 reviews)

Ocean view, Tiki, Heated Pool, Game Room - The Seahorse - Roelens
Fort Myers Beach
Ocean view, Tiki, Heated Pool, Game Room - The Seahorse - Roelens
Fort Myers Beach
- Pool
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (67 reviews)
9.8/10
Exceptional
(67 reviews)

Location! Welcome To Bare Feet Retreat. Steps From Times Square And The Beach
Fort Myers Beach
Location! Welcome To Bare Feet Retreat. Steps From Times Square And The Beach
Fort Myers Beach
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (114 reviews)
10/10
Exceptional
(114 reviews)

Canal Front 4 Bedroom 3 Bath home, with elevator, pool & heated spa. No steps!
Mid Island
Canal Front 4 Bedroom 3 Bath home, with elevator, pool & heated spa. No steps!
Mid Island
- Pool
- Hot tub
- Kitchen
- Washing machine
9.0 out of 10, Wonderful, (17 reviews)
9.0/10
Wonderful
(17 reviews)

244 Flamingo | Canal Front Home with Dock & Private Pool!
Mid Island
244 Flamingo | Canal Front Home with Dock & Private Pool!
Mid Island
- Pool
- Hot tub
- Kitchen
- Washing machine
9.4 out of 10, Exceptional, (18 reviews)
9.4/10
Exceptional
(18 reviews)

🌊Gorgeous Harbor Views | Private Elevator | Premier Island Escape🌊
Fort Myers Beach
🌊Gorgeous Harbor Views | Private Elevator | Premier Island Escape🌊
Fort Myers Beach
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)

Island Villa with 33 Foot Infinity Pool, Dock and Boat Access, Dolphin Visits
Fort Myers Beach
Island Villa with 33 Foot Infinity Pool, Dock and Boat Access, Dolphin Visits
Fort Myers Beach
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (62 reviews)
10/10
Exceptional
(62 reviews)

⚓Anchors Away: Private Pool | Pet Friendly | Fenced Yard⚓
Fort Myers Beach
⚓Anchors Away: Private Pool | Pet Friendly | Fenced Yard⚓
Fort Myers Beach
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (15 reviews)
10/10
Exceptional
(15 reviews)

Charming Fort Myers Beach home suited for families
South Island
Charming Fort Myers Beach home suited for families
South Island
- Pool
- Hot tub
- Kitchen
- Washing machine
9.8 out of 10, Exceptional, (72 reviews)
9.8/10
Exceptional
(72 reviews)

AMAZING RATES & RAVE REVIEWS! Stunning private pool! 3min walk to the Beach 🏖
Mid Island
AMAZING RATES & RAVE REVIEWS! Stunning private pool! 3min walk to the Beach 🏖
Mid Island
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (33 reviews)
10/10
Exceptional
(33 reviews)

Dolphin House : pool home on the Gulf of Mexico : walk to the beach
Bonita Beach
Dolphin House : pool home on the Gulf of Mexico : walk to the beach
Bonita Beach
- Ocean view
- Pool
- Kitchen
- Washing machine
9.8 out of 10, Exceptional, (114 reviews)
9.8/10
Exceptional
(114 reviews)

⛱️Private Pool, Canal Front Private Home with Dock-Beach House Paradise⛱️
Mid Island
⛱️Private Pool, Canal Front Private Home with Dock-Beach House Paradise⛱️
Mid Island
- Pool
- Kitchen
- Washing machine
- Dryer
9.2 out of 10, Wonderful, (5 reviews)
9.2/10
Wonderful
(5 reviews)

Family, heated Pool hot/tub, Dogs ok, 400' from Beach, Fast WIFI. Fishing. Dock
Mid Island
Family, heated Pool hot/tub, Dogs ok, 400' from Beach, Fast WIFI. Fishing. Dock
Mid Island
- Pool
- Hot tub
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (31 reviews)
10/10
Exceptional
(31 reviews)

Large 5BR Home | Pool, Bonus Rooms & Walk to Beach & Dining
TP Hill's
Large 5BR Home | Pool, Bonus Rooms & Walk to Beach & Dining
TP Hill's
- Pool
- Hot tub
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (42 reviews)
10/10
Exceptional
(42 reviews)
